Isomerases;
Racemases and epimerases;
Acting on amino acids and derivatives
BRITE hierarchy

penicillin-N 5-amino-5-carboxypentanoyl-epimerase

isopenicillin N = penicillin N [RN:R04147]

R04147
Reaction

isopenicillin N [CPD:C05557]

This enzyme contains pyridoxal phosphate. Epimerization at C-5 of the 5-amino-5-carboxypentanoyl group to form penicillin N is required to make a substrate for EC 1.14.20.1, deactoxycephalosporin-C synthase, to produce cephalosporins. Forms part of the penicillin biosynthesis pathway (for pathway, click here).

EC 5.1.1.17 created 2002

1  [PMID:2804141]

Usui S, Yu CA

Purification and properties of isopenicillin N epimerase from Streptomyces clavuligerus.

Biochim Biophys Acta 999:78-85 (1989)
DOI:10.1016/0167-4838(89)90033-2

[ag:AAA26714]

2

Laiz, L., Liras, P., Castro, J.M. and Martin, J.F.

Purification and characterization of the isopenicillin-N epimerase from Nocardia lactamdurans.

J Gen Microbiol 136:663-671 (1990)

3  [PMID:1354366]

Cantwell C, Beckmann R, Whiteman P, Queener SW, Abraham EP.

Isolation of deacetoxycephalosporin C from fermentation broths of Penicillium chrysogenum transformants: construction of a new fungal biosynthetic pathway.

Proc R Soc Lond B Biol Sci 248:283-9 (1992)
DOI:10.1098/rspb.1992.0073

4

Yeh, W.K., Ghag, S.K. and Queener, S.W.

Enzymes for epimerization of isopenicillin N, ring expansion of penicillin N, and 3'-hydroxylation of deacetoxycephalosporin C. Function, evolution, refolding, and enzyme engineering.

Ann NY Acad Sci 672:396-408 (1992)