B1638

Sigma-Aldrich

Benzoyl coenzyme A lithium salt

≥90%

Synonym(s):
Benzoyl CoA lithium salt
Empirical Formula (Hill Notation):
C28H40N7O17P3S
CAS Number:
Molecular Weight:
871.64
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥90%

storage temp.

−20°C

SMILES string

[Li].CC(C)(COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)n2cnc3c(N)ncnc23)C(O)C(=O)NCCC(=O)NCCSC(=O)c4ccccc4

InChI

1S/C28H40N7O17P3S.Li.H/c1-28(2,22(38)25(39)31-9-8-18(36)30-10-11-56-27(40)16-6-4-3-5-7-16)13-49-55(46,47)52-54(44,45)48-12-17-21(51-53(41,42)43)20(37)26(50-17)35-15-34-19-23(29)32-14-33-24(19)35;;/h3-7,14-15,17,20-22,26,37-38H,8-13H2,1-2H3,(H,30,36)(H,31,39)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43);;

InChI key

HBWPXONQNHVILU-UHFFFAOYSA-N

General description

Benzoyl coenzyme A (Benzoyl CoA) is an intermediate in the CoA-dependent epoxide pathway, synthesized from benzoate in the presence of the enzyme benzoate-CoA ligase. It is further converted to 2,3-epoxybenzoyl-CoA and this step is catalyzed by benzoyl-CoA reductase (BoxA) and benzoyl-CoA oxygenase(BoxB).

Packaging

5 mg in glass bottle

Biochem/physiol Actions

Benzoyl coenzyme A (Benzoyl CoA) is a substrate of benzoyl-CoA reductase (box A) and a starter substrate for type-III polyketide synthase. It also acts as a substrate for plant enzymes biphenyl synthase (BIS) and benzophenone synthase (BPS). Benzoyl CoA is an effector of gentisate pathway of the bacteria, Comamonas testosteroni. It may also be used as a substrate for the characterization of specific alcohol acyltransferases and N-acyltransferase assays.
Benzoyl coenzyme A (Benzoyl CoA) may be used in studies of benzoate metabolism. Benzoyl CoA is a component of benzoyl-coenzyme A (CoA) oxidizing epoxidase enzyme system BoxAB. Benzoyl CoA may also be used as a substrate for characterization of specific alcohol acyltransferases. Benzoyl-CoA may be used as a starter substrate for synthesis of biphenyl and dibenzofuran phytoalexins (polyketide derivatives).

storage_class_code

13 - Non Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

A versatile biosynthetic approach to amide bond formation
Philpott HK, et al.
Green Chemistry, 20(15), 3426-3431 (2018)
Liv J Rather et al.
Biochimica et biophysica acta, 1814(12), 1609-1615 (2011-06-16)
BoxA is the reductase component of the benzoyl-coenzyme A (CoA) oxidizing epoxidase enzyme system BoxAB. The enzyme catalyzes the key step of an hitherto unknown aerobic, CoA-dependent pathway of benzoate metabolism, which is the epoxidation of benzoyl-CoA to the non-aromatic...
Mariam M Gaid et al.
Journal of plant physiology, 168(9), 944-951 (2011-02-19)
Sorbus aucuparia cell cultures accumulate biphenyl and dibenzofuran phytoalexins in response to elicitor treatment. These polyketide derivatives arise from the starter substrate benzoyl-CoA, the biosynthesis of which is largely unresolved. Two CoA ligases involved are cinnamate:CoA ligase and benzoate:CoA ligase...
Liv J Rather et al.
The Journal of biological chemistry, 286(33), 29241-29248 (2011-06-03)
The coenzyme A (CoA)-dependent aerobic benzoate metabolic pathway uses an unprecedented chemical strategy to overcome the high aromatic resonance energy by forming the non-aromatic 2,3-epoxybenzoyl-CoA. The crucial dearomatizing reaction is catalyzed by three enzymes, BoxABC, where BoxA is an NADPH-dependent...
Catrin S Günther et al.
Phytochemistry, 72(8), 700-710 (2011-04-01)
Volatile esters are key compounds of kiwifruit flavour and are formed by alcohol acyltransferases that belong to the BAHD acyltransferase superfamily. Quantitative RT-PCR was used to screen kiwifruit-derived expressed sequence tags with proposed acyltransferase function in order to select ripening-specific...

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