Isobutyryl-CoA

Last updated
Isobutyryl-CoA
Isobutyryl-coenzyme A.png
Names
IUPAC name
3′-O-Phosphonoadenosine 5′-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methylpropanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl dihydrogen diphosphate]
Systematic IUPAC name
O1-{{#parsoidfragment:0}}{[(2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methyl} O3-[(3R)-3-hydroxy-2,2-dimethyl-4-{[3-({2-[(2-methylpropanoyl)sulfanyl]ethyl}amino)-3-oxopropyl]amino}-4-oxobutyl] dihydrogen diphosphate
Other names
Isobutyryl-coenzyme A
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
MeSH Isobutyryl-coenzyme+A
PubChem CID
  • InChI=1S/C25H42N7O17P3S/c1-13(2)24(37)53-8-7-27-15(33)5-6-28-22(36)19(35)25(3,4)10-46-52(43,44)49-51(41,42)45-9-14-18(48-50(38,39)40)17(34)23(47-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,34-35H,5-10H2,1-4H3,(H,27,33)(H,28,36)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/t14-,17-,18-,19+,23-/m1/s1 X mark.svgN
    Key: AEWHYWSPVRZHCT-NDZSKPAWSA-N X mark.svgN
  • CC(C)C(=O)SCCNC(=O)CCNC(=O)C(C(C)(C)COP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)(O)O)O
Properties
C25H42N7O17P3S
Molar mass 837.62 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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Isobutyryl-coenzyme A is a necessary cofactor required for Polyketide synthase (PKS) enzyme(s), to catalyze the a,b-dehydrogenation of acyl-CoA esters to make many natural products via Polyketide synthase (PKS) assembly lines, as well as PKS-NRPS hybrid assembly lines. The resulting products comprise antibiotics and other bioactive molecules. Notably, isobutyryl-coenzyme A is also an intermediate in the metabolism of the amino acid valine, and it is structurally similar to intermediates in the catabolism of other small amino acids.

Defective Isobutyryl-coenzyme A, produced by the body, often results in a metabolic disease. [1] [2]

See also

References

  1. ↑ Nguyen, Tien V; Andresen, Brage S; Corydon, Thomas J; Ghisla, Sandro; Abd-El Razik, Nasser; Mohsen, Al-Walid A; Cederbaum, Stephen D; Roe, Diane S; Roe, Charles R; Lench, Nicolas J; Vockley, Jerry (2002-09-01). "Identification of isobutyryl-CoA dehydrogenase and its deficiency in humans". Molecular Genetics and Metabolism. 77 (1): 68–79. doi:10.1016/S1096-7192(02)00152-X. ISSN   1096-7192.
  2. ↑ "XIE, Zhenhua, Chan ZHANG, Xian LI, Linfei LI, Mengjun XIAO, Rui LI, Shuying LUO, Yaodong ZHANG, and Dongxiao LI. "3-Hydroxy-isobutyryl-coenzyme A hydrolase deficiency: a case report and literature review."". Chinese Journal of Neurology: 348-354. 2021.


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