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I9381

Sigma-Aldrich

Isovaleryl coenzyme A lithium salt hydrate

≥90%

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Synonym(s):
IV-CoA
Empirical Formula (Hill Notation):
C26H44N7O17P3S · xLi+ · yH2O
Molecular Weight:
851.65 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24896155
NACRES:
NA.51

Quality Level

200

Assay

≥90%

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].[H]O[H].CC(C)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)([O-])=O)n2cnc3c(N)ncnc23

InChI

1S/C26H44N7O17P3S.3Li.H2O/c1-14(2)9-17(35)54-8-7-28-16(34)5-6-29-24(38)21(37)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-20(49-51(39,40)41)19(36)25(48-15)33-13-32-18-22(27)30-12-31-23(18)33;;;;/h12-15,19-21,25,36-37H,5-11H2,1-4H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41);;;;1H2/q;3*+1;/p-3/t15-,19-,20-,21+,25-;;;;/m1..../s1

InChI key

RABPIYFVNICBEC-YVBWDKSKSA-K

Related Categories

General description

Isovaleryl coenzyme A is an intermediate in leucine catabolism. Iv-CoA is synthesized from β-methylbutyric acid by the action of enzyme acyl CoA synthetase. The conversion of isovaleryl-CoA to methylcrotonyl-CoA is catalyzed by the enzyme isovaleryl-CoA dehydrogenase in leucine catabolism pathway. The enzyme isovaleryl-CoA oxidase also calalyzes this conversion in fatty acid β-oxidation pathway.

Application

Isovaleryl coenzyme A (IV-CoA ) lithium salt hydrate may be used:
  • as substrate for β-Hydroxy-β-methylbutyric acid synthesis in cell-free extracts from G. reessii
  • in high-performance liquid chromatography (HPLC) for the characterization of IV-CoA from lymphocytes
  • as a substrate in isovaleryl-CoA dehydrogenase assay

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tobias Bock et al.
Nucleic acids research, 45(4), 2166-2178 (2016-12-13)
Isovaleryl coenzyme A (IV-CoA) is an important building block of iso-fatty acids. In myxobacteria, IV-CoA is essential for the formation of signaling molecules involved in fruiting body formation. Leucine degradation is the common source of IV-CoA, but a second, de
Lee et al.
Archives of microbiology, 169(3), 257-262 (1998-03-28)
Galactomyces reessii accomplishes the enzymatic transformation of beta-methylbutyric acid (isovaleric acid) to beta-hydroxy-beta-methylbutyric acid. The enzymatic basis for this bioconversion was evaluated by analyzing cell-free extracts of G. reessii for enzyme activities commonly associated with leucine catabolism. G. reessii extracts
K Däschner et al.
Plant physiology, 126(2), 601-612 (2001-06-13)
We recently identified a cDNA encoding a putative isovaleryl-coenzyme A (CoA) dehydrogenase in Arabidopsis (AtIVD). In animals, this homotetrameric enzyme is located in mitochondria and catalyzes the conversion of isovaleryl-CoA to 3-methylcrotonyl-CoA as an intermediate step in the leucine (Leu)
G Tajima et al.
Journal of inherited metabolic disease, 27(5), 633-639 (2005-01-27)
Maple syrup urine disease (MSUD) is caused by a congenital defect of the branched-chain alpha-ketoacid dehydrogenase complex (BCKADC), and is one of the target disorders in newborn screening. However, it is not always easy to confirm the diagnosis; conventional methods
Helge B Bode et al.
Journal of bacteriology, 188(18), 6524-6528 (2006-09-06)
Isovaleryl-coenzyme A (IV-CoA) is the starting unit for some secondary metabolites and iso-odd fatty acids in several bacteria. According to textbook biochemistry, IV-CoA is derived from leucine degradation, but recently an alternative pathway that branches from the well-known mevalonate-dependent isoprenoid
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