Biomolecules Notes
Biomolecules Notes
biochenmistry.
CARBOHYDRATES
Hydrates of carbon having general formula, C,(H,O), is known carbohydrates.
                                                            as
For example. glucose (CH,0) fits into the general formula, C(H,O)
                                                               not considered as
But all the compounds having general formula C,(H,O), are
                                                            fits into this general
carbohydrates. For example, Ethanoic acid (CHCOOH)
                   but it is not a carbohydrate. Also, all carbohydrates do
                                                                               not
formula,   C(H,O)2,
fit into the   general formula C(H,O), e.g.,   rhamnose   (CH,20). Chemically
                                                                    or ketones
carbohydrates are defined as optically active polyhydroxy aldehydes
or the compounds which produce such
                                        units on hydrolysis. Carbohydrates are
                                                            which are sweet to
also known as saccharides. Some of the carbohydrates
taste, are also called sugars.
Classification of         Carbohydrates :
                                                                   can   be divided
On the basis     of their behaviour upon hydrolysis, carbohydrates
intothree main groups
                                                                           into
)     Monosaccharides : A          carbohydrate which cannot be hydrolyzed
                                                                ketone is called
      simpler unit of polyhydroxy aldehyde
                                                           or
              (CHO,), + nH,O
                                                       nCHO,
               Starch or Cellulose                     Glucose
      Sugar and non-sugars : In general monosaccharides                             and   oligosaccharides,   are   crystalline solids, soluble in
      wate and sweet to              taste,    are   collectively     known    as sugars. The polysaccharides,             on the other
                                                                                                                                            hand,   ar
      amorphous insoluble            in water and       tasteless,     are   known as non-sugars.
      Reducing         and    non-reducing carbohydrates                      The   carbohydrates containing        free   aldehydic (-C-H) o
      ketonic    (C      =
                              0) group
                                    reduce Fehling's solution and Tollen's reagent are known
                                              can                                                                                      as
                                                                                                                                              reducing
      carbohydrates. All monosacchanides whether aldose or ketose are reducing in nature.
      The   carbohydrates in which the reducing parts are                    not free cannot reduce     Fehling's solution    and Tollen's reagent
      are   known as non-reducing carbohydrates.
      For   example,         in sucrose       reducing part      of   glucose    is bonded with the       reducing part       of fructose. So this
      disaccharide is non-reducing. All disaccharides except sucrose are reducing in nature.
All polysaccharides like starch, cellulose, glycogen etc. are non-reducing carbohydrates.
Monosaccharides
      fa monosaccharide contains                  an   aldehyde       group, it is known    as an   aldose and if it contains          keto
                                                                                                                                   a          group,it
      is known as a ketose.
Preparation of Glucose
                                                                             H                     nCHO
                                         (CHp),+ nH,O                   393 K; 2-3 bar
                                          Starch or
                                                                                                    Glucose
                                          Cellulose
Structure of Glucose
                                                                                                                        cellulose etc. It is
   Glucose is an aldohexose and is the
                                                 monomer       of many      larger carbohydrates like starch,
                                                 on    the Earth.
   the most abundant     organic compound
CHO CH N-OH
                                                                      CN
                               CHO                             CHK
                                                               OH
                                                 HCN
                               (CHOH)                          (CHOH)                Cyanohydrin of glucose
                                                (1 eq.)
                               CHOH                            CHOH
acid upon oxidation with mild-oxidising agents like Bromin water, Tollen's reagent, Fehling's solution ete
CHO CoOH
                                                        Br,-Water
                                             (CHOH),                  (CHOH)          Gluconic acid
CH,OH CH,OH
                                         CHO                                          CHO
                                                           5(CH,CO),o
                                                          (Acetic anhydride)
                                         (CHOH),                                      (CH-0-C-CH)
                                                                                                O
                                         CH,OH                                        CH-O-C-CH,
                This confirms the presence of five -OH groups attached to different carbon atoms in glucose.
 6.         Presence of Primary Alcoholic (CH,2 - OH) Group : On oxidation with nitric acid, glucose as well as
            gluconic acid both yield the dicarboxylic acid, saccharic acid.
                                      (CHOH)
                                                       HNO                             HNO
                                                                     (CHOH)                   (CHOH).
7.     Spatial Arrangement of -OH Groups: The exact spatial arrangement of 5- OH groups in glucose was
       provided by Fischer after studying many other properties of it. The configuration of open chain structure
       ofglucose can be represented by Fischer projection formula as
                                                                        CHO
                                                                               - OH
                                                                H
HO- -H
H -OH
H- OH
                                                                        CH,OH
                                                                 D(+)-Glucose
      Glucose is corectly named as D(+) - Glucose. 'D' before the name of glucose represents the configuration
     whereas+            represents dextrorotatory nature       ofthe molecule. It should be noted that there is no direct
     relation between D, L configurations with d and I or (+) or (-) notations.
 Limitations of      Open   Chain Structure of Glucose
      The open chain structure of glucose explains most of the properties of glucose except following ones
     1.     Although glucose has an aldehydic group. it does not give, 2, 4-DNP test, Schiff's test and also it de
            not react with NaHSO, or NH, to form addition product.
     2.     The pentacetate of glucose formed upon acetylation of glucose, daoes not react with hydroxylamine, Thi
            indicates the absence of aldehydic (-CHO) group.
     3.    The existence of   glucose     in   a   and   B- anomeric   forms could not be   explained by the open chain structura
           The   a-form  of glucose having m.p. 419 K is obtained by crystallising form of concentrated
                                                                                                        solution                of
           glucose   at 303 K while the B-form having m.p. 423 K is obtained by crystallising of hot and
                                                                                                                         saturated
           aqueous solution at 371 K.
                     H-C-OH                                 H                                     HO-C-H
                     H           OH                         H           OH                          H        OH
                   HO         -H                            HO           H                       HO           HO
                   H          OH                              H         OH                          H4       OH
                     H                                        H        OH                           H
Pyran
  Pyran is a six membered ring with one oxygen and five carbon atoms in the ring. The cyclic structure of glucose
  is more   correcty represented by Haworth structure as given                t
                                      CHOH                                         CHOH
                              H                             H                      H
                                                                                    5         OOH
                                      OH                                           OH
                            HO        3                     OH               HO                      H
                                                                                    3
                                      H              OH                            H           OH
                          a-D-(+)-Glucopyranose                              B-D-(+)-Glucopyranose
Fructose and Its Structure
    Fructose is an important ketohexose. It is obtained by the hydrolysis of sucrose. On the basis of molecula
    weight determination, elemental analysis and various reaction its molecular formula is found
                                                                                                                  to be   H29, and
    open chain structure of it can be written as
CH,OH
                                                               HO--H
                                                               HFOH
                                                               HFOH
                                                                 CH,OH
                                                               D-(--Fructose
    It contains a ketonic functional group at C-2 and six-carbon atoms in straight chain. Naturally occuring fructose
Furan
Furan is a five-membered cyclic compound with one oxygen and four carbon atoms.
                                                                                    HO-C-CHOH
                                     HOH,C-C-OH
                                         HO        H                                 HO            H
H OH H OH
                                          H                                          H
                                               CH,OH                                       CH,OH
                                        o-D-(--Fructofuranose                       B-D---Fructofuranose
                                                                                                           structures as:
                                                   of fructose     can   be represented    by Haworth
    The   cyclic   structures    of two anomers
                                                           1                          6
                                 HOH,C                     CHOH               HOHC             O           OH
                                                   OH/OH                                   H       OH/CH,OH
                                         HH        3                                               3
                                              OH       H                                   OH          H
a-D-(--Fructofuranose P-D-(--Fructofuranose
           Ci2H22011
              Lactose
                                   »CsH1205+
                                      Glucose
                                              CsH120
                                               Galactose
                              HO
           C2H22011
             Maltose
                                        CgH20+CsH120s
                                         Glucose Glucose
 In   disaccharides the two monosaccharides units                           are joined together by           an    oxide    linkage formed by    the loss
 of   a   water molecule and the          linkage     is known         as   glycosidic linkage.
The disacharides may be                 reducing      or   non-reducing depending upon                  the      position   of   linkage between the   two
monosaccharide units.
() Sucrose
Sucrose is formed by the glycosidic linkage between C-1 of a-D-(+)-9lucose and C, of p-D-(-) fructose :
                                         CH
                                   H                  O          H          HOHC
                                         H
                                                                       **********
                                         OH                                                            HO
                               HO
                                                                     ************         3              4       CHOH
                                                                                                                  6
                                                                     Glycosidic           OH                 H
                                         H             OH             linkage
          As the reducing parts of glucose and fructose are involved in glycosidic linkage, sucrose is a non-reducing
          sugar.
          Sucrose is dextrorotatory in nature but upon hydrolysis it gives the equimolar mixture of D-glucose
          (l+52.5) and D-fructose (o, = -92.4) which is laevorotatory. Thus the hydrolysis of sucrose changes
          the sign of rotation, from dextro (+) to laevo () and the product so formed is known as invert sugar.
(i)       Maitose : Maltose is formed by the glycosidic linkage between C-1 of one glucose unit to the C-4 of
          another glucose unit.
                                                                                              6
                                             CHOH                                             CH,OH
                                    H                             H                   H                             H
                                          H                                                   H
                                          OH               H                                  OH
                                   HO
                                                           2          -0                                            OH
                                                                                               3
                                             H              OH                                H              OH
                                                 ()                                                   (11)
                                         a-D-Glucose                                              a-D-Glucose
                                                                        Maltose
          Maltose is a reducing sugar because the C-1 of second glucose unit is not involved in glycosidic linkage
          and in solution it can show
                                                reducing properties    so   it is   a   reducing sugar.
   (ii)   Lactose: Lactose is found in milk so it is also
                                                           known as milk sugar. It is formed                          by the glycosidic
          linkage between C-1 of B-D-galactose unit and C-4 of
                                                               B-D-glucose unit.
                                                6
                                                CH,OH                                     CH,OH
                                      HO                    O.                      H
                                                                                                         O    OH
                                                                                          H
                                                OH               H B-linkage              QH
                                          H                                                                   H
                                                H           OH                             H             OH
                                                B-D-Galactose                                  B-D-Glucose
                                                                       Lactose
Polysaccharides
   Polysaccharides are long chain polymer of monosaccharides joined together by glycosidic linkages. For
   example, starch, cellulose. glycogen etc. They mainly act as the food storage or structural materials.
   Starch    (CH,O), : Starch             is the main     storage polysaccharide of plants. High content of starch          is found in
   cereals, roots, tubers and            some   vegetables.
          (CgH,OhasslaseC2H2,0,1                                   CH20g:D-glucose
                Starch                        Maltose
    Starch is  polymer of a-D-(+) Glucose coming of two components namely Amylose and
                a
    is water soluble
                                                                                            Amylopectin. Amylose
                    component, which constitutes about 15 20% of starch. It is a straight chain polysaccharide
    containing a-D-(+Hglucose units joined together by a-glycosidic linkage involving C-1 of one glucose unit and
    C4 of the next. It can have 200 1000
                                            o-D-(+-glucose units held by C1 C4 glycosidic linkage.   -
                                                        a-Link                                   o-Link
                                                                   Amylose
    Amylopectin          isbranched chain
                                  a
                                                            polysaccharide
                                                                        insoluble in water. It constitutes about
    80      85% starch. It is a branched chain
                                                          polymer of a-D-glucose units in which chain is formed by
    C1-C4 glycosidic linkage             whereas branching occurs by C1 C6 glycosidic linkage.
                       CH,OH                           CH,OH
H O,
                       OH      H        -0             OH
                                                                         -link
H OH H OH
                                                                             Branch at C
                                    CH,OH                                CH                                 CH,OH
                               H                   H                                       H            H
                                    H                                    H
OH OH O OH
H OH H OH H OH
                                                            -Link                              0-Link
                                                                         Amylopectin
Cellulose
    Cellulose is a straight chain polysaccharide composed of only B-D-glucose units. In cellulose there is B-
    glycosidic linkages between C-1 of one glucose unit and C-4 of the next glucose unit. Cellulose occurs mainly
    in plants and it is the most abundant organic substance in plant kingdom. It is the chief constituent of the
    cell walls of plants.
                                                              HOH,C
                                                                             -o O
                                                                     OH
                                              HOHC
                                                                                OH
OH
                                                              OH
                                    HOH,C
                                                                                               B-links
                                         OH
                                               OH
                                                               Cellulose
Glycogen
   Its structure is similar to amylopectin with more branching than in amylopectin. It is also known as animal
   starch. In body, carbohydrates are stored as glycogen and when the body needs glucose, enzymes break the
   glycogen down to glucose. Glycogen is present in liver, muscle and brain. It is also found in yeast and fung.
Importance of Carbohydrates
   Carbohydrates are essential for life in both plants and animals. Carbohydrates are stored in plant as starch
   and in animals as glycogen. Cell wall of bacteria and plant is made up of cellulose. Furniture used in daily
   life, are made              in the form of wood, clothe we wear is also made from cellulose in the form of
                   fromcellulose
   cotton fibre.
PROTEINS
    The term protcin is           the
                        derived from     Greek word Proteins' which means of prime importance. Proteins are high
   molecular mass complex biopolymer of oa-amino acids present in all living cells. They occur in every part of the
   body and form the fundamental basis of structure and functions of life.
  Proteins are the most abundant biomolecules of theliving system. Chief sources of proteins are milk. cheese
  pulses, peanuts, fish etc.
 Amino Acids: The compoundcontaining-NH, and-COOH functional groups are known as amino acid, depending
 upon the relative position of -NH, group with respect to -coOH group, amino acids are classified into a, B. 7,8
 and so on amino acid. Hydrolysis of proteins gives only a-amino acids represented as
                                                R-CH-COOH
                                                   NH2
 Proteins may contain other functional groups also.
Nomenclature of a-Amino Acids: All a-amino acids have their trival names which generally reflect the property
 of the
          amino acids or their sources. For example, glycine is so named since it has sweet taste (in Greek, Glycos
means cheese)
       meufa-G7lyine Aim
  Classification of Amino Acids: Dependingupon the relative number of amino and carboxyl groups in the moiecuies
  amino acids are classified as acidic, basic or neutral, depending upon the relative number of amino and carboxyi
  groups. Equal numberof-NH, &-CoOH groups make the amino acid neutral, more -NH, group than-coo
  group make the amino acid basicand more -COOH group than-NH, groupmake the amino acid acidic.> ( l u t a
  Essential and non-essential amino acids:Theáminoacidswhich cannot be synthesized in the body are known
  as
     essential amino acids which must be taken through diet. The amino acids, which can be synthesized in the A              e
  body are known as non-essential amino acids.                                                                             aud
  Physical Properties of a-Amino Acids: Amino acids are generally colourless, crystalline, water-soluble, hign
  melting solids.They behave like salts rather than simple amines or carboxylic acids due to the presence of both-
  COOH&-NH, groups
   n aqueous solution amino acid can exist as a dipolar ion known as zwitter ion if-COOH group loses H        ion and-
                      O
           between-C- and-NH-groups             ofthe peptide bond.
H9
                                                                                   N
                                                                                                N            N
                                                                                 RCH           RCH        RCH
                                                     H                           C-O-HNC0-H-NC-0
                                                                               O-CR                 HCR      HCR
                                                    N                            HCR            N-H--O=C
                                                                                    N-H-O-C
                                                                                                                 N-H
                                                                                 RÇH           RCH           RCH
                                                                              ~H-NHCRCO-- HCR
                                                                                           0-H-N R
                                                                                  C             C            C
          CO of an adjacent tum of the helix as shown above figure. In B-structure all peptide chains are strelcheo
          out to nearly maximum extension and then laid side by side which are held together by intermolecular
          H-bonds. The structure resembles the pleated folds of drapery and therefore is known as B-pleated sheet.
      (3)   Tertiary Structure: The tertiary structure of proteins represents overallfolding of the polypeptide chains i.e,
            further folding of secondary structure. It gives rise to two major molecular shapes namely fibrous and globular.
            The main forces which stabilizesthe 2°&3° structures of proteins are hydrogen bonds, disulphide linkages,
            van   der Waals and electrostatic forces of attraction.
      (4)   Quatermary Structure: Some of the proteins are composed of two or more polypeptide chains referred to as
            Sub units. Ihe spatial arrangement of these subunits with respect to each other is known as quaternary
            structure.
eseeo bee
egeed
    Denaturation    of Proteins :
                                  The lossinbiological activity of a protein due to unfolding of globules and uncoiling of
    helix is called denaturation of protein. During denaturation secondary and tertiary structures are destroyed but
    primary structure remains intact. The coagulation of egg white on boiling is a common example of denaturation.
    Another example is curding of milk which is caused due to the formation of lactic acid by the bacteria present in
    milk. The reverse of denaturation is called renaturation.
                                                          Urea      CO, + NH
     (vi)          Urease
                                                          Proteins> amino acids
    vi) Pepsin
                                                          Proteins amino acids
    (vii) Trypsin
    (ix) Diastase                                        Starch      Maltose
   Efficiency: Even a            small amount of enzymes are          highly efficient. This is because their molecules are regenerated
   during their catalytic activity.
                 Those chemical substances which tend to reduce activity of a             particular enzyme are called enzyme inhibitors.
VITAMINS
     Vitamins   are   organic compounds which   are   essential for normal growth of life for animals, some bacteria and
  micro organism. Vitamins not synthesized
                                are
  through food. They are essential dietary factor.
                                                      by animals (except vitamin D). Vitamins are supplied to the organiem
                   Deficiency Diseases: Skin swelling around the mouth. Cracking of lips at the edges, bulging of eye
                   cells.
           (c)     Vitamin-B, : Niacin (Nicotinic Acid) and Nicotinamide
                   Natural Sources: Mushroom, Ground nut,
                                                          Bread etc.
                   Deficiency Disease: Pellagra
           (d)     Vitamin B,: Pantothenic
                   Natural Sources : Ground nut,    Soyabean, Liver, Kidney
                   Deficiency Disease: Swelling in stomach and intestines
           (e)     Vitamin B: Pyridoxine
                   Natural Sources     Yeast milk, Egg yolk, Cereals, Grams
                  Deficiency Disease: Convulsions
       (           Vitamin B12: Cyanocobalamine
                   Natural Sources: Meat, Fish,     Egg, Curd, Milk   etc.
                   Deficiency disease: Pernicious anemia, degradation of nervous system.
           (9)    Vitamin   C:Ascrobic Acid
                  Natural   source:   Citrus fruits, Amla and Green   leafy vegetables.
                  Deficiency disease: Scurvy, tooth decrease bleeding of gums.
(2)        Fat Soluble Vitamins
           (a)    Vitamin-A: Retinol
                   Natural Sources Fish liver oil, Carrots, Butter and Milk
                  Natural Sources: Spinach and      other green leafy vegetables, tomato, potato, cabbage, edible oil, liver
                  etc.
                                                    Enzyme, Nuclease
                            Nucleic Acid                                       Nucleotide
                                                                                    NH,
                                                  MgO in H,0/A
                                                                           H,PO,+      Nucleoside
                                                                                    Ho
                                                                               Sugar+Heterocyclic bases
      Sugars:    Two sugars     present    in   nucleic acid     are   ribose and   deoxyribose.
      Ribose is present in RNA and         deoxyribose in DNA.
      These sugars    are   present in furanose form.
     Bases     These are derivatives of purine and pyrimidine.
                                    1
                                    N                                                   N3
                                                Purine                           Pyrimidine
    Purine Bases:
                                        NH
                     HC
                                        C=N                                                   NH
                       NC          -N           CH
                                                                          N CN                     NH
                            H                                              H
                             NH,
                                                  H                      H
                                                                                         HC           NH
                             C                                       N
                      HC            N
                                                                                         HC
                      HC     N
                                                         HC
                                                                 N
                                                                 H
                                                                         O=o                     N
                                                                                                 H
                                                                                                          o
                                H
                                                                                             Uracil (U)
                                                              Thymine (T)
                           Cytosine (C)
                                                                                5
                            5
                                                       Base   O-P-0-H,C                               Base
                 HO- HC                   O-
                                                   /H                           H                 H/H
                             HH
                                                                                     OH           OH
                                    OH            OH
                                    Nucleoside                                          Nucleotide
                                          Base                                                                Base
                                                                               O-P-0-CH,
         O-P-0-CH,
                O
                                                                                                      Sugar
                                 Sugar
                                                                               Phosphodiester 3
                                                                               linkage                O
                                    OH
O-P O
                                                                                                               Base
                                                                                                     5'CH,
                                               |Base
            O-P-0-CH,                                                                                  o
                                    0                                                                      Sugar
                                     Sugar                                                                3
                                                                                                          OH
                                    OH                                                        3'end of chain
                                              chain is as shown    below.
                    version   of nucleic acid
    A simplified
                                     Base                        Base
           Base
     nfarmmation reaarding the sequence of nucleotides in the chain of a nucleic acid is called its primary structure.
    Ncleic acids have a secondary structure also. Two nucleic acid chains are held together by hydrogen bonds
    hehween pairs of bases. Adenine forms hydrogen bonds with thymine whereas cytosine forms hydrogen bonds
    with guanine.
    in secondany structure of RNA, helices are present which are only single stranded. Sometimes they fold back
    on   themselves to form a double helix sturcture.
                                                       5
                                                       GE
                                                        A=T-
                                                             T=A-
                                                                  ET-
                                                           C=G-
                                                           G=CC
                                                           T=A-
                                                           C=G
T=
                                                           GEC
                                                           A=T-
                                                                   T-A
                                                            A==T
                                                              -T=A-
                                                           -C=G
                                                       G=C
                                                   5              3'
                                            Double strand helix structure for DNA
Example 5:        The third component present     alongwith deoxyribose     and a base in DNA   is
Solution          Phosphoric acid.