HMG-CoA

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HMG-CoA
HMG coenzyme A.svg
Names
IUPAC name
(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
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.014.820
MeSH HMG-CoA
Properties
C27H44N7O20P3S
Molar mass 911.661 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

β-Hydroxy β-methylglutaryl-CoA (HMG-CoA), also known as 3-hydroxy-3-methylglutaryl-CoA, is an intermediate in the mevalonate and ketogenesis pathways. It is formed from acetyl CoA and acetoacetyl CoA by HMG-CoA synthase. The research of Minor J. Coon and Bimal Kumar Bachhawat in the 1950s at University of Illinois led to its discovery.[1][2]

HMG-CoA is a metabolic intermediate in the metabolism of the branched-chain amino acids, which include leucine, isoleucine, and valine.[3] Its immediate precursors are β-methylglutaconyl-CoA (MG-CoA) and β-hydroxy β-methylbutyryl-CoA (HMB-CoA).[4][5][6]

Biosynthesis[edit]

Mevalonate pathway[edit]

HMG-CoA reductase converts it into mevalonic acid.

Mevalonate pathway

Ketogenesis pathway[edit]

HMG-CoA lyase breaks it into acetyl CoA and acetoacetate.

See also[edit]

References[edit]

  1. ^ Debi P. Sarkar (2015). "Classics in Indian Medicine" (PDF). The National Medical Journal of India (28): 3. Archived from the original (PDF) on 2016-05-31.
  2. ^ Avadhesha Surolia (1997). "An outstanding scientist and a splendid human being" (PDF). Glycobiology. 7 (4): v–ix. doi:10.1093/glycob/7.4.453.
  3. ^ "Valine, leucine and isoleucine degradation - Reference pathway". Kyoto Encyclopedia of Genes and Genomes. Kanehisa Laboratories. 27 January 2016. Retrieved 1 February 2018.
  4. ^ 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.
  5. ^ 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
    Figure 8.57: Metabolism of L-leucine