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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)

Quality Level

100

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

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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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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