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D5269

Sigma-Aldrich

Decanoyl coenzyme A monohydrate

≥90%

Synonym(s):

Capryl CoA monohydrate, Decanoyl CoA monohydrate

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About This Item

Linear Formula:
C31H54N7O17P3S
CAS Number:
Molecular Weight:
939.80
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

Assay

≥90%

form

powder

storage temp.

−20°C

SMILES string

O.CCCCCCCCCC(=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/C31H54N7O17P3S.H2O/c1-4-5-6-7-8-9-10-11-22(40)59-15-14-33-21(39)12-13-34-29(43)26(42)31(2,3)17-52-58(49,50)55-57(47,48)51-16-20-25(54-56(44,45)46)24(41)30(53-20)38-19-37-23-27(32)35-18-36-28(23)38;/h18-20,24-26,30,41-42H,4-17H2,1-3H3,(H,33,39)(H,34,43)(H,47,48)(H,49,50)(H2,32,35,36)(H2,44,45,46);1H2/t20-,24-,25-,26+,30-;/m1./s1

InChI key

IRILGPHKFKSRQN-ASEPKIFHSA-N

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General description

Decanoyl coenzyme A is a substrate for acyltransferase. It is a substrate for human liver glycine-N-acylase.

Application

Decanoyl coenzyme A (Decanoyl CoA) is coupled with S-adenosylmethionine (SAM) by Vibrio cholera CqsA enzyme to produce a potent quorum-sensing molecule, 3-aminotridec-2-en-4-one (Ea-CAI-1.
Decanoyl coenzyme A monohydrate has been used in the phosphatidylinositol 4,5-bisphosphate inhibition studies (LC-CoA) and in the human diacylglycerol acyltransferase 1 and 2 assays.

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

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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Jocelyn E Manning Fox et al.
Metabolism: clinical and experimental, 52(10), 1313-1319 (2003-10-18)
Recent evidence demonstrates that long-chain acyl coenzyme A esters (CoAs) activate cardiac and beta-cell plasma-membrane (pmK(ATP)) adenosine triphosphate (ATP)-sensitive potassium channels. In this study, we have investigated the differential effects of acyl CoAs of short and medium side-chain length on
Nasrin Jahan et al.
Journal of molecular biology, 392(3), 763-773 (2009-07-28)
CqsA is an enzyme involved in the biosynthesis of cholerae autoinducer-1 (CAI-1), the major Vibrio cholerae autoinducer engaged in quorum sensing. The amino acid sequence of CqsA suggests that it belongs to the family of alpha-oxoamine synthases that catalyse the
Fouzia A Sattar et al.
Chemical communications (Cambridge, England), 46(19), 3348-3350 (2010-05-06)
Alpha-methylacyl-CoA racemase (AMACR; P504S) catalysed exchange of straight-chain fatty acyl-CoA alpha-protons. One alpha-proton was removed in each catalytic cycle, with the pro-S proton preferred. This reaction was most efficient for straight-chain substrates with longer side-chains. 2-Methyldecanoyl-CoA underwent alpha-proton exchange 3x
Purification and characterization of acyl coenzyme A: alcohol acyltransferase of Neurospora sp.
Yamauchi H, et al.
Agricultural and Biological Chemistry, 53(6), 1551-1556 (1989)
Yunzhou Wei et al.
ACS chemical biology, 6(4), 356-365 (2011-01-05)
Vibrio cholerae, the causative agent of the disease cholera, uses a cell to cell communication process called quorum sensing to control biofilm formation and virulence factor production. The major V. cholerae quorum-sensing signal CAI-1 has been identified as (S)-3-hydroxytridecan-4-one, and

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