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Merck
CN

A2852

Sigma-Aldrich

δ-(L-α-Aminoadipyl)-Cys-D-Val

≥95% (HPLC)

Synonym(s):

ACV

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About This Item

Empirical Formula (Hill Notation):
C14H25N3O6S
Molecular Weight:
363.43
MDL number:
UNSPSC Code:
12352200
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Assay

≥95% (HPLC)

storage temp.

−20°C

SMILES string

CC(C)[C@@H](NC(=O)[C@H](CSSC[C@H](NC(=O)CCC[C@H](N)C(O)=O)C(=O)N[C@H](C(C)C)C(O)=O)NC(=O)CCC[C@H](N)C(O)=O)C(O)=O

Other Notes

ACV is the key intermediate in the biosynthesis of all penicillins and cephalosporins by eukaryotic and prokaryotic microorganisms.

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W Kallow et al.
FEBS letters, 414(1), 74-78 (1997-09-26)
The tripeptide delta-L-alpha-aminoadipyl-L-cysteinyl-D-valine (LLD-ACV) is synthesised by the multifunctional enzyme ACV synthetase integrating four steps of the penicillin and cephalosporin biosynthetic pathway. Peptide synthesis follows the thiotemplate mechanism from intermediates bound as thioesters to the enzyme. The formation of delta-(L-alpha-aminoadipyl)-L-cysteinyl-thioester
P Adriaens et al.
Antimicrobial agents and chemotherapy, 8(6), 638-642 (1975-12-01)
Cultures of Penicillium chrysogenum, growth with [(35)S]sulfate or labeled amino acids, were examined by ion-exchange chromatography for possible peptidic precursors of penicillin. A sulfur-containing compound, present in both the mycelial extracts and the culture filtrates, was eluted at the location
P L Roach et al.
Nature, 387(6635), 827-830 (1997-06-19)
The biosynthesis of penicillin and cephalosporin antibiotics in microorganisms requires the formation of the bicyclic nucleus of penicillin. Isopenicillin N synthase (IPNS), a non-haem iron-dependent oxidase, catalyses the reaction of a tripeptide, delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-valine (ACV), and dioxygen to form isopenicillin N

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