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H2012

Sigma-Aldrich

Hexanoyl coenzyme A trilithium salt hydrate

≥85%

Synonym(s):

Caproyl Coenzyme A trilithium salt

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About This Item

Empirical Formula (Hill Notation):
C27H43Li3N7O17P3S · xH2O
CAS Number:
103476-19-3
Molecular Weight:
883.48 (anhydrous basis)
UNSPSC Code:
41106305
PubChem Substance ID:
24895496
NACRES:
NA.51

Quality Level

200

assay

≥85%

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].O.CCCCCC(=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/C27H46N7O17P3S.3Li.H2O/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34;;;;/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42);;;;1H2/q;3*+1;/p-3/t16-,20-,21-,22+,26-;;;;/m1..../s1

InChI key

YMMJFYLVSRICJX-ZTADYLHKSA-K

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Application

Hexanoyl coenzyme A trilithium salt hydrate may be used as a standard for liquid chromatography-tandem mass spectrometry (LC-MS/MS).

Biochem/physiol Actions

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Hexanoyl CoA is involved in fatty acid oxidation, lipid biosynthesis, and ceramide formation. Ghrelin O-acyltransferase (GOAT) has a preference for n-hexanoyl-CoA over n-octanoyl-CoA as an acyl donor. Hexanoyl CoA is also used as a starter unit for polyketide biosynthesis.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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LC-MS/MS-based analysis of coenzyme A and short-chain acyl-coenzyme A thioesters
Neubauer S, et al.
Analytical and Bioanalytical Chemistry, 407(22), 6681-6688 (2015)
Nobutaka Funa et al.
The Biochemical journal, 367(Pt 3), 781-789 (2002-07-26)
RppA, which belongs to the type III polyketide synthase family, catalyses the synthesis of 1,3,6,8-tetrahydroxynaphthalene (THN), which is the key intermediate of melanin biosynthesis in the bacterium Streptomyces griseus. The reaction of THN synthesis catalysed by RppA is unique in
Miao He et al.
The Journal of biological chemistry, 278(39), 37974-37986 (2003-07-12)
Rat and human short/branched chain acyl-CoA dehydrogenases exhibit key differences in substrate specificity despite an overall amino acid identity of 85% between them. Rat short/branched chain acyl-CoA dehydrogenases (SBCAD) are more active toward substrates with longer carbon side chains than
Hideko Ohgusu et al.
Biochemical and biophysical research communications, 386(1), 153-158 (2009-06-09)
Ghrelin is a peptide hormone in which serine 3 is modified by n-octanoic acid through GOAT (ghrelin O-acyltransferase). However, the enzymological properties of GOAT remain to be elucidated. We analyzed the in vitro activity of GOAT using the recombinant enzyme.
C M D Swarbrick et al.
Acta crystallographica. Section D, Biological crystallography, 71(Pt 4), 986-995 (2015-04-08)
Acyl-CoA thioesterases catalyse the hydrolysis of the thioester bonds present within a wide range of acyl-CoA substrates, releasing free CoASH and the corresponding fatty-acyl conjugate. The TesB-type thioesterases are members of the TE4 thioesterase family, one of 25 thioesterase enzyme

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