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28007

Sigma-Aldrich

Crotonoyl coenzyme A trilithium salt

~90% (HPLC)

Synonym(s):

trans-2-Butenoyl coenzyme A trilithium salt

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About This Item

Empirical Formula (Hill Notation):
C25H37Li3N7O17P3S
Molecular Weight:
853.41
MDL number:
MFCD00151226
UNSPSC Code:
41106305
PubChem Substance ID:
57648286
NACRES:
NA.51

Assay

~90% (HPLC)

form

solid

impurities

≤10% water

solubility

H2O: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].C\C=C\C(=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/C25H40N7O17P3S.3Li/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32;;;/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40);;;/q;3*+1/p-3/b5-4+;;;/t14-,18-,19-,20+,24-;;;/m1.../s1

InChI key

LUYQFKSDLNQLEG-OUWZIDFPSA-K

Application

Crotonoyl coenzyme A (Crotonoyl -CoA) may be used in anti-tubercular and anti-malarial drug research as a substrate to help identify and characterized enzymes such as Plasmodium falciparum enoyl-ACP reductase (PfENR) and other enoyl-CoA reductases that may be effective drug targets. Crotonoyl -CoA may be used as a substrate analogue for kinetic studies on ß-hydroxyacyl-acyl carrier protein (ACP) dehydratase (FabZ).

Other Notes

Oxidation-reduction of general acyl-CoA dehydrogenase by the butyryl-CoA/crotonyl-CoA couple; Purification of rat liver microsomal trans-2-enoyl-CoA reductase

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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A new β-hydroxyacyl-acyl carrier protein dehydratase (FabZ) from Helicobacter pylori: Molecular cloning, enzymatic characterization, and structural modeling.
Liu W, Luo C, Han C, Peng S, et al.
Biochemical and Biophysical Research Communications, 12, 1078-1086 (2005)
Purification of rat liver microsomal trans-2-enoyl-CoA reductase.
C F Chiang
Preparative biochemistry, 17(4), 315-325 (1987-01-01)
Peng Liao et al.
Biochemical and biophysical research communications, 524(3), 730-735 (2020-02-10)
Post-translational modifications (PTMs) play pivotal roles in controlling the stability and activity of the tumor suppressor p53 in response to distinct stressors. Here we report an unexpected finding of a short chain fatty acid modification of p53 in human cells.
L M Schopfer et al.
Biochemistry, 27(17), 6599-6611 (1988-08-23)
Pig kidney general acyl-CoA dehydrogenase (GAD) can be reduced by butyryl-CoA to form reduced enzyme and crotonyl-CoA. This reaction is reversible. Stopped-flow, kinetic investigations on GAD have been made, using the following reaction pairs: oxidized GAD/butyryl-CoA, oxidized GAD/crotonyl-CoA, oxidized GAD/alpha,beta-dideuteriobutyryl-CoA
Mili Kapoor et al.
The Biochemical journal, 381(Pt 3), 725-733 (2004-05-06)
The binding of enoyl-ACP (acyl-carrier protein) reductase from Plasmodium falciparum (PfENR) with its substrates and inhibitors has been analysed by SPR (surface plasmon resonance). The binding of the substrate analogue crotonoyl-CoA and coenzyme NADH to PfENR was monitored in real
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