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B1638

Sigma-Aldrich

Benzoyl coenzyme A lithium salt

≥90%

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Synonym(s):
Benzoyl CoA lithium salt
Empirical Formula (Hill Notation):
C28H40N7O17P3S
CAS Number:
102185-37-5
Molecular Weight:
871.64
MDL number:
MFCD00078942
UNSPSC Code:
41106305
PubChem Substance ID:
24891603
NACRES:
NA.51

Quality Level

200

Assay

≥90%

form

solid

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).

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).

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Cornelia Chizzali et al.
Beilstein journal of organic chemistry, 8, 613-620 (2012-05-09)
Biphenyls and dibenzofurans are the phytoalexins of the Pyrinae, a subtribe of the plant family Rosaceae. The Pyrinae correspond to the long-recognized Maloideae. Economically valuable species of the Pyrinae are apples and pears. Biphenyls and dibenzofurans are formed de novo
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
A versatile biosynthetic approach to amide bond formation
Philpott HK, et al.
Green Chemistry, 20(15), 3426-3431 (2018)
Duo Wang et al.
Nature communications, 13(1), 1369-1369 (2022-03-18)
Lysine benzoylation (Kbz) is a recently discovered post-translational modification associated with active transcription. However, the proteins for maintaining and interpreting Kbz and the physiological roles of Kbz remain elusive. Here, we systematically characterize writer, eraser, and reader proteins of histone
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