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'''HMG-CoA''' (or '''3-hydroxy-3-methylglutaryl-coenzyme A''') is an intermediate in the [[mevalonate pathway|mevalonate]] and [[ketogenesis]] pathways. It is formed from [[acetyl CoA]] and [[acetoacetyl CoA]] by [[HMG-CoA synthase]]. The researches of [[Minor J. Coon]] and [[Bimal Kumar Bachhawat]] in the 1950s at [[University of Illinois]] led to its discovery.<ref name="Classics in Indian Medicine">{{cite journal | url=http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf | title=Classics in Indian Medicine | author=Debi P. Sarkar | journal=The National Medical Journal of India | year=2015 | issue=28 | pages=3}}</ref><ref name="An outstanding scientist and a splendid human being">{{cite journal | url=https://glycob.oxfordjournals.org/content/7/4/453.1.full.pdf | title=An outstanding scientist and a splendid human being | author=[[Avadhesha Surolia]] | journal=Glycobiology | year=1997 | volume=7 | issue=4 | pages=v–ix | doi = 10.1093/glycob/7.4.453}}</ref>
'''HMG-CoA''' (or '''3-hydroxy-3-methylglutaryl-coenzyme A''') is an intermediate in the [[mevalonate pathway|mevalonate]] and [[ketogenesis]] pathways. It is formed from [[acetyl CoA]] and [[acetoacetyl CoA]] by [[HMG-CoA synthase]]. The researches of [[Minor J. Coon]] and [[Bimal Kumar Bachhawat]] in the 1950s at [[University of Illinois]] led to its discovery.<ref name="Classics in Indian Medicine">{{cite journal | url=http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf | title=Classics in Indian Medicine | author=Debi P. Sarkar | journal=The National Medical Journal of India | year=2015 | issue=28 | pages=3 | deadurl=yes | archiveurl=https://web.archive.org/web/20160531082638/http://www.nmji.in/archives/Volume-28/Issue-3/Classics-in-Indian-Medicine.pdf | archivedate=2016-05-31 | df= }}</ref><ref name="An outstanding scientist and a splendid human being">{{cite journal | url=https://glycob.oxfordjournals.org/content/7/4/453.1.full.pdf | title=An outstanding scientist and a splendid human being | author=[[Avadhesha Surolia]] | journal=Glycobiology | year=1997 | volume=7 | issue=4 | pages=v–ix | doi = 10.1093/glycob/7.4.453}}</ref>


It is also an intermediate in the metabolism of [[leucine]]. Its immediate precursor is [[3-methylglutaconyl CoA]].
It is also an intermediate in the metabolism of [[leucine]]. Its immediate precursor is [[3-methylglutaconyl CoA]].

Revision as of 08:59, 27 October 2017

HMG-CoA
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 Edit this at Wikidata
MeSH HMG-CoA
  • 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 checkY
    Key: CABVTRNMFUVUDM-VRHQGPGLSA-N checkY
  • 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
    Key: CABVTRNMFUVUDM-VRHQGPGLBX
  • O=C(O)C[C@@](O)(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n2cnc1c(ncnc12)N)[C@H](O)[C@@H]3OP(=O)(O)O
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).
checkY verify (what is checkY☒N ?)

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

It is also an intermediate in the metabolism of leucine. Its immediate precursor is 3-methylglutaconyl CoA.

Mevalonate pathway

Main article: Mevalonate pathway

HMG-CoA reductase converts it into mevalonic acid.

Mevalonate pathway

Ketogenesis pathway

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

Ketogenesis

See also

References

  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. {{cite journal}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  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.


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