HMG-CoA

HMG-CoA
이름
	IUPAC 이름 (9R,21S)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9,21-tetrahydroxy-8,8,21-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide
	기타 이름 3-hydroxy-3-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl coenzyme A
식별자
CAS 번호	1553-55-5 ;
3D 모델(JSmol)	인터랙티브 이미지;
체비	체비:61659 ;
켐스파이더	392859 ;
ECHA InfoCard	100.014.820
IUPHAR/BPS	3040;
메슈	HMG-CoA
펍켐 CID	445127;
CompTox 대시보드 (EPA)	DTXSID00935181 ;
	인치 InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1 키: CABVTRNMFUDM-VRHQGPGPSA-N ; InChI=1/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1 키: CABVTRNMFUDM-VRHQGPGPBX;
	스마일즈 O=C(O)C[C@](O)CC(=O)SCNC(=O)CC(=O)[C@H]C(C)COP(=O)COP(=O)OP(O)O.OC[C@H]3O[C@H](n2cnc1c(nc12)N)[C@H](O)[C@H]3OP(=O)(O)o;
특성.
화학식	C27H44N7O20P3S
어금질량	911.661 g/190
	달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
	이버라이시(?)
	Infobox 참조 자료

β-히드록시 β-메틸글루타릴-CoA(HMG-CoA)는 3-히드록시-3-메틸글루타릴 코엔자임 A로도 알려져 있으며 메발로네이트 및 케토제네시스 경로의 중간이다.HMG-CoA synthase에 의해 아세틸 CoA와 아세토아세틸 CoA로 형성된다.1950년대 일리노이 대학에서 Minor J. Coon과 Bimal Kumar Bachhawat의 연구는 그 발견을 이끌었다.^[1]^[2]null

HMG-CoA는 leucine, isoleucine, valine을 포함하는 분기 체인 아미노산의 신진대사 중간 물질이다.^[3]그것의 즉각적인 전구체는 β-메틸글루타코닐-코아(MG-CoA)와 β-히드로xy β-메틸부티릴-코아(HMB-CoA)이다.^[4]^[5]^[6]null

HMG-CoA 환원효소는 콜레스테롤의 생합성에 필요한 단계인 메발론산으로 HMG-CoA의 변환을 촉진한다.null

생합성

인간 내 류신 대사

Diagram of leucine, HMB, and isovaleryl-CoA metabolism in humans

엘루신

브랜치 체인아미노
산성아미노트란스페라아제

근육: α-케투아소카프로이트(α-KIC)

간: α-케투아소카프로이트(α-KIC)

브랜치 체인 α-케토아시드데히드로제아제
(미토콘드리아)

KIC-다이옥시겐아제
(사이토솔)

이소발레릴-CoA

β-히드록시
β-메틸부티레이트
(HMB)

배설됨
소변으로
(10–40%)

HMB-CoA

β-히드록시 β-메틸글루타릴-CoA
(HMG-CoA)

β-메틸크로토닐-코아
(MC-CoA)

β-메틸글루타코닐-CoA
(MG-CoA)

CO₂

O₂

CO₂

H₂O

CO₂

H₂O

알 수 없는
효소

L-루신 대비 HMB 및 이소밸러리-CoA에 대한 인체 대사 경로.^[4]^[7]^[6]두 가지 주요 경로 중 L-루신은 대부분 이소발레릴-CoA로 대사되는 반면 약 5%만이 HMB로 대사된다.^[4]^[7]^[6]

메발론산길

메발로네이트 합성은 아세틸-CoA의 두 분자의 베타-케토티올라제-분석된 클라이센 응축으로 시작하여 아세토아세틸 CoA를 생성한다.다음 반응은 아세틸-CoA와 아세토아세틸-CoA가 결합하여 HMG-CoA 싱타아제에 의해 촉매되는 프로세스인 HMG-CoA를 형성하는 것이다.^[8]null

메발로네이트 생합성성의 마지막 단계에서 NADPH에 의존하는 산화효소인 HMG-CoA 환원효소는 HMG-CoA를 메발로네이트로 변환하는 촉매제로서 이 경로의 1차 규제 지점이다.메발로네이트는 인간의 콜레스테롤을 포함한 다양한 최종 산물에 통합된 이소프로노이드 그룹의 전구체 역할을 한다.^[9]null

메발론산길

케토제네시스 경로

HMG-CoA 리아제는 그것을 아세틸 CoA와 아세토아세테이트로 분해한다.null

케토제네시스

참고 항목

스테로이드 유발 효소

참조

^ Sarkar DP (2015). "Classics in Indian Medicine" (PDF). The National Medical Journal of India (28): 3. Archived from the original (PDF) on 2016-05-31.
^ Surolia A (1997). "An outstanding scientist and a splendid human being". Glycobiology. 7 (4): v–ix. doi:10.1093/glycob/7.4.453.
^ "Valine, leucine and isoleucine degradation - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories. 27 January 2016. Retrieved 1 February 2018.
^ ^a ^b ^c Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". Journal of the International Society of Sports Nutrition. 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064. PMID 23374455.
^ Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids. 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. S2CID 11120110. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).
^ ^a ^b ^c Kohlmeier M (May 2015). "Leucine". Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. pp. 385–388. ISBN 978-0-12-387784-0. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
그림 8.57: L-루신의 대사
^ ^a ^b Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids. 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. S2CID 11120110. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).
^ Garrett RH (2013). Biochemistry. Cengage Learning. p. 856. ISBN 978-1-305-57720-6.
^ Haines BE, Steussy CN, Stauffacher CV, Wiest O (October 2012). "Molecular modeling of the reaction pathway and hydride transfer reactions of HMG-CoA reductase". Biochemistry. 51 (40): 7983–95. doi:10.1021/bi3008593. PMC 3522576. PMID 22971202.

이 생화학 기사는 단조롭다.위키피디아를 확장하여 도울 수 있다.

[Classics_in_Indian_Medicine-1] Sarkar DP (2015). "Classics in Indian Medicine" (PDF). The National Medical Journal of India (28): 3. Archived from the original (PDF) on 2016-05-31.

[An_outstanding_scientist_and_a_splendid_human_being-2] Surolia A (1997). "An outstanding scientist and a splendid human being". Glycobiology. 7 (4): v–ix. doi:10.1093/glycob/7.4.453.

[HMG_biosynthesis-3] "Valine, leucine and isoleucine degradation - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories. 27 January 2016. Retrieved 1 February 2018.

[ISSN_position_stand_2013-4] Wilson JM, Fitschen PJ, Campbell B, Wilson GJ, Zanchi N, Taylor L, Wilborn C, Kalman DS, Stout JR, Hoffman JR, Ziegenfuss TN, Lopez HL, Kreider RB, Smith-Ryan AE, Antonio J (February 2013). "International Society of Sports Nutrition Position Stand: beta-hydroxy-beta-methylbutyrate (HMB)". Journal of the International Society of Sports Nutrition. 10 (1): 6. doi:10.1186/1550-2783-10-6. PMC 3568064. PMID 23374455.

[HMB_athletic_performance-related_effects_2011_review-5] Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids. 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. S2CID 11120110. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).

[Leucine_metabolism-6] Kohlmeier M (May 2015). "Leucine". Nutrient Metabolism: Structures, Functions, and Genes (2nd ed.). Academic Press. pp. 385–388. ISBN 978-0-12-387784-0. Retrieved 6 June 2016. Energy fuel: Eventually, most Leu is broken down, providing about 6.0kcal/g. About 60% of ingested Leu is oxidized within a few hours ... Ketogenesis: A significant proportion (40% of an ingested dose) is converted into acetyl-CoA and thereby contributes to the synthesis of ketones, steroids, fatty acids, and other compounds
그림 8.57: L-루신의 대사

[HMB_athletic_performance-related_effects_2011_reviewb-7] Zanchi NE, Gerlinger-Romero F, Guimarães-Ferreira L, de Siqueira Filho MA, Felitti V, Lira FS, Seelaender M, Lancha AH (April 2011). "HMB supplementation: clinical and athletic performance-related effects and mechanisms of action". Amino Acids. 40 (4): 1015–1025. doi:10.1007/s00726-010-0678-0. PMID 20607321. S2CID 11120110. HMB is a metabolite of the amino acid leucine (Van Koverin and Nissen 1992), an essential amino acid. The first step in HMB metabolism is the reversible transamination of leucine to [α-KIC] that occurs mainly extrahepatically (Block and Buse 1990). Following this enzymatic reaction, [α-KIC] may follow one of two pathways. In the first, HMB is produced from [α-KIC] by the cytosolic enzyme KIC dioxygenase (Sabourin and Bieber 1983). The cytosolic dioxygenase has been characterized extensively and differs from the mitochondrial form in that the dioxygenase enzyme is a cytosolic enzyme, whereas the dehydrogenase enzyme is found exclusively in the mitochondrion (Sabourin and Bieber 1981, 1983). Importantly, this route of HMB formation is direct and completely dependent of liver KIC dioxygenase. Following this pathway, HMB in the cytosol is first converted to cytosolic β-hydroxy-β-methylglutaryl-CoA (HMG-CoA), which can then be directed for cholesterol synthesis (Rudney 1957) (Fig. 1). In fact, numerous biochemical studies have shown that HMB is a precursor of cholesterol (Zabin and Bloch 1951; Nissen et al. 2000).

[8] Garrett RH (2013). Biochemistry. Cengage Learning. p. 856. ISBN 978-1-305-57720-6.

[9] Haines BE, Steussy CN, Stauffacher CV, Wiest O (October 2012). "Molecular modeling of the reaction pathway and hydride transfer reactions of HMG-CoA reductase". Biochemistry. 51 (40): 7983–95. doi:10.1021/bi3008593. PMC 3522576. PMID 22971202.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

Search

HMG-CoA

네임스페이스

더

목차

생합성

메발론산길

케토제네시스 경로

참고 항목

참조

이름

IUPAC 이름 (9R,21S)-1-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]-3,5,9,21-tetrahydroxy-8,8,21-trimethyl-10,14,19-trioxo-2,4,6-trioxa-18-thia-11,15-diaza-3,5-diphosphatricosan-23-oic acid 3,5-dioxide
기타 이름 3-hydroxy-3-methylglutaryl CoA; 3-hydroxy-3-methylglutaryl coenzyme A
식별자
CAS 번호	1553-55-5^Y
3D 모델(JSmol)	인터랙티브 이미지
체비	체비:61659^Y
켐스파이더	392859^Y
ECHA InfoCard	100.014.820
IUPHAR/BPS	3040
메슈	HMG-CoA
펍켐 CID	445127
CompTox 대시보드 (EPA)	DTXSID00935181
인치 InChI=1S/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1^Y 키: CABVTRNMFUDM-VRHQGPGPSA-N^Y InChI=1/C27H44N7O20P3S/c1-26(2,21(40)24(41)30-5-4-15(35)29-6-7-58-17(38)9-27(3,42)8-16(36)37)11-51-57(48,49)54-56(46,47)50-10-14-20(53-55(43,44)45)19(39)25(52-14)34-13-33-18-22(28)31-12-32-23(18)34/h12-14,19-21,25,39-40,42H,4-11H2,1-3H3,(H,29,35)(H,30,41)(H,36,37)(H,46,47)(H,48,49)(H2,28,31,32)(H2,43,44,45)/t14-,19-,20-,21+,25-,27+/m1/s1 키: CABVTRNMFUDM-VRHQGPGPBX
스마일즈 O=C(O)C[C@](O)CC(=O)SCNC(=O)CC(=O)[C@H]C(C)COP(=O)COP(=O)OP(O)O.OC[C@H]3O[C@H](n2cnc1c(nc12)N)[C@H](O)[C@H]3OP(=O)(O)o
특성.
화학식	C₂₇H₄₄N₇O₂₀P₃S
어금질량	911.661 g/190
달리 명시된 경우를 제외하고, 표준 상태(25°C [77°F], 100 kPa)의 재료에 대한 데이터가 제공된다.
이버라이시^YN(?)
Infobox 참조 자료