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Key Documents

O6877

Sigma-Aldrich

Octanoyl coenzyme A lithium salt hydrate

≥95% (HPLC)

Synonym(s):

Capryloyl coenzyme A lithium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C29H50N7O17P3S · xLi+ · yH2O
CAS Number:
Molecular Weight:
893.73 (free acid basis)
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

assay

≥95% (HPLC)

form

powder

solubility

H2O: soluble-25 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].O.CCCCCCCC(=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/C29H50N7O17P3S.3Li.H2O/c1-4-5-6-7-8-9-20(38)57-13-12-31-19(37)10-11-32-27(41)24(40)29(2,3)15-50-56(47,48)53-55(45,46)49-14-18-23(52-54(42,43)44)22(39)28(51-18)36-17-35-21-25(30)33-16-34-26(21)36;;;;/h16-18,22-24,28,39-40H,4-15H2,1-3H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44);;;;1H2/q;3*+1;/p-3/t18-,22-,23-,24+,28-;;;;/m1..../s1

InChI key

VWXPWBSHKDXAFH-SMMZWZJBSA-K

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Application

Coenzyme A functions as an acyl group carrier, acetyl-CoA. Octanoyl coenzyme A is a donor molecule for the acylation (octanylation) of Ghrelin and other peptides by ghrelin O-acyltransferase(s) (GOAT).

Biochem/physiol Actions

Medium-chain fatty acid covalently linked to coenzyme A.

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)

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The expression of ghrelin O-acyltransferase (GOAT) in human tissues.
Lim CT, Kola B, Grossman A, Korbonits M.
Endocrine J., 58, 707-710 (2011)
Amparo Romero et al.
European journal of endocrinology, 163(1), 1-8 (2010-04-28)
The ghrelin-ghrelin receptor system is one of the most important mechanisms regulating energy balance and metabolism. Among other actions, central and peripheral administration of ghrelin increases food intake and adiposity. During the last years, many efforts have been made in
Tomoko Takahashi et al.
Journal of biochemistry, 146(5), 675-682 (2009-07-25)
Ghrelin was originally isolated from rat stomach as an endogenous ligand for the GH secretagogue receptor. The major active form of ghrelin is a 28-amino acid peptide modified by an n-octanoic acid on the serine 3 residue, and this lipid
Jesus A Gutierrez et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(17), 6320-6325 (2008-04-30)
The peptide hormone ghrelin is the only known protein modified with an O-linked octanoyl side group, which occurs on its third serine residue. This modification is crucial for ghrelin's physiological effects including regulation of feeding, adiposity, and insulin secretion. Despite
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.

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