Acetoacetyl-CoA

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Acetoacetyl-CoA
Acetoacetyl coenzyme A.svg
Names
Preferred IUPAC name
S-{(9R)-1-[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]-3,5,9-trihydroxy-8,8-dimethyl-3,5,10,14-tetraoxo-2,4,6-trioxa-11,15-diaza-3λ5,5λ5-diphosphaheptadecan-17-yl} 3-oxobutanethioate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH acetoacetyl+CoA
  • InChI=1S/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1 checkY
    Key: OJFDKHTZOUZBOS-CITAKDKDSA-N checkY
  • InChI=1/C25H40N7O18P3S/c1-13(33)8-16(35)54-7-6-27-15(34)4-5-28-23(38)20(37)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-19(49-51(39,40)41)18(36)24(48-14)32-12-31-17-21(26)29-11-30-22(17)32/h11-12,14,18-20,24,36-37H,4-10H2,1-3H3,(H,27,34)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t14-,18-,19-,20+,24-/m1/s1
    Key: OJFDKHTZOUZBOS-CITAKDKDBD
  • O=C(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
C25H40N7O18P3S
Molar mass 851.609 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Acetoacetyl CoA is the precursor of HMG-CoA in the mevalonate pathway, which is essential for cholesterol biosynthesis. It also takes a similar role in the ketone bodies synthesis (ketogenesis) pathway of the liver. In the ketone bodies digestion pathway (in the tissue), it is no longer associated with having HMG-CoA as a product or as a reactant.

It is created from acetyl-CoA, a thioester, which reacts with the enolate of a second molecule of acetyl-CoA in a Claisen condensation reaction,[1] and it is acted upon by HMG-CoA synthase to form HMG-CoA. During the metabolism of leucine, this last reaction is reversed. Some individuals may experience Acetoacetyl-CoA deficiency.[2] This deficiency is classified as a disorder ketone body and isoleucine metabolism that can be inherited.[3]

Mevalonate pathway

Additionally, it reacts with NADPH-dependent acetoacetyl-coenzyme A reductase, also known as PhaB, in a pathway that produces polyester polyhydroxyalkanoate (PHA). The reduction of acetoacetyl-coA by Pha creates (R)-3-hydroxybutyryl-CoA, which polymerizes to PHA.[4] The pathway is present in bacteria such as Ralstonia eutropha and the PCC6803 strain of Synechocystis.[5]

References

  1. ^ Bruice PY (2017). Organic chemistry. Pearson. ISBN 978-0-13-404228-2. OCLC 974910578.
  2. ^ Tsuda H, Shiraki M, Inoue E, Saito T (August 2016). "Generation of poly-β-hydroxybutyrate from acetate in higher plants: Detection of acetoacetyl CoA reductase- and PHB synthase- activities in rice". Journal of Plant Physiology. 201: 9–16. doi:10.1016/j.jplph.2016.06.007. PMID 27372278.
  3. ^ Bose KS, Sarma RH (October 1975). "Delineation of the intimate details of the backbone conformation of pyridine nucleotide coenzymes in aqueous solution". Biochemical and Biophysical Research Communications. 66 (4): 1173–1179. doi:10.1016/0006-291x(75)90482-9. PMID 2.
  4. ^ Matsumoto K, Tanaka Y, Watanabe T, Motohashi R, Ikeda K, Tobitani K, et al. (October 2013). "Directed evolution and structural analysis of NADPH-dependent Acetoacetyl Coenzyme A (Acetoacetyl-CoA) reductase from Ralstonia eutropha reveals two mutations responsible for enhanced kinetics". Applied and Environmental Microbiology. 79 (19): 6134–6139. doi:10.1128/aem.01768-13. PMC 3811355. PMID 23913421.
  5. ^ Taroncher-Oldenburg G, Nishina K, Stephanopoulos G (October 2000). "Identification and analysis of the polyhydroxyalkanoate-specific beta-ketothiolase and acetoacetyl coenzyme A reductase genes in the cyanobacterium Synechocystis sp. strain PCC6803". Applied and Environmental Microbiology. 66 (10): 4440–4448. doi:10.1128/aem.66.10.4440-4448.2000. PMC 92322. PMID 11010896.

See also:

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