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I9381

Sigma-Aldrich

Isovaleryl coenzyme A lithium salt hydrate

≥90%

Synonym(s):

IV-CoA

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About This Item

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

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

I9381-5MG:
I9381-BULK:
I9381-VAR:
I9381-10MG:
I9381-1MG:

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
Taifo Mahmud et al.
Chembiochem : a European journal of chemical biology, 6(2), 322-330 (2004-12-28)
A biosynthetic shunt pathway branching from the mevalonate pathway and providing starter units for branched-chain fatty acid and secondary metabolite biosynthesis has been identified in strains of the myxobacterium Stigmatella aurantiaca. This pathway is upregulated when the branched-chain alpha-keto acid
Helge B Bode et al.
Chembiochem : a European journal of chemical biology, 10(1), 128-140 (2008-10-11)
Isovaleryl-CoA (IV-CoA) is usually derived from the degradation of leucine by using the Bkd (branched-chain keto acid dehydrogenase) complex. We have previously identified an alternative pathway for IV-CoA formation in myxobacteria that branches from the well-known mevalonate-dependent isoprenoid biosynthesis pathway.
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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