KEGG   PATHWAY: rn00311
Entry
rn00311                     Pathway                                

Name
Penicillin and cephalosporin biosynthesis
Description
Penicillins (Penams) and cephalosporins (cephems) are beta-lactam antibiotics containing 6-aminopenicillanate (6-APA) and 7-aminocephalosporanate (7-ACA) nuclei, respectively. 6-APA and 7-ACA are key intermediates for a variety of semisynthetic penicillin and cephalosporin derivatives. Penicillins are produced only by fungi, while cephalosporins (including cephamycins) are produced by fungi and bacteria. Both antibiotics are synthesized from L-2-aminoadipate, L-cysteine and L-valine through a common pathway. It starts with the condensation of these three amino acids by the non-ribosomal peptide synthetase to form the tripeptide delta-(L-2-aminoadipyl)-L-cysteinyl-D-valine (ACV). The linear ACV tripeptide is then converted to bicyclic isopenicillin N by isopenicillin N synthase, in which the beta-lactam ring is formed. Isopenicillin N is the branch point of penicillin [MD:M00672] and cephalosporin [MD:M00673] pathways.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
rn00311  Penicillin and cephalosporin biosynthesis
rn00311

Module
M00672  Penicillin biosynthesis, aminoadipate + cycteine + valine => penicillin [PATH:rn00311]
M00673  Cephamycin C biosynthesis, aminoadipate + cycteine + valine => cephamycin C [PATH:rn00311]
Reaction
R02170  Penicillin amidohydrolase
R03062  Cephalosporin-C acetylhdrolase
R03063  cephalosporin-C:2-oxoglutarate aminotransferase
R03064  acetyl-CoA:deacetylcephalosporin-C O-acetyltransferase
R04147   
R04870  L-2-aminohexanedioate:L-cysteine:L-valine ligase (AMP-forming, valine-inverting)
R04872   
R05229   
R05230   
R05301  penicillin-N,2-oxoglutarate:oxygen oxidoreductase (ring-expanding)
R05302   
R05303   
R06361  Acyl-CoA:isopenicillin N N-acyltransferase
R06363  Penicillin hydrolase
R07400  cephalosporin C:oxygen oxidoreductase (deaminating)
R07401   
R07402  (7R)-7-(4-carboxybutanamido)cephalosporanate amidohydrolase
Compound
C00097  L-Cysteine
C00183  L-Valine
C00395  Penicillin
C00916  Cephalosporin C
C00956  L-2-Aminoadipate
C02954  6-Aminopenicillanate
C03112  Deacetylcephalosporin C
C04712  (7R)-7-(5-Carboxy-5-oxopentanoyl)aminocephalosporinate
C05556  delta-(L-2-Aminoadipyl)-L-cysteinyl-D-valine
C05557  Isopenicillin N
C06564  Penicillin N
C06565  Deacetoxycephalosporin C
C06566  Cephamycin C
C06567  Penicilloic acid
C06568  O-Carbamoyl-deacetylcephalosporin C
C06569  7a-Hydroxy-O-carbamoyl-deacetylcephalosporin C
C07756  7-Aminocephalosporanic acid
C15666  (7R)-7-(4-Carboxybutanamido)cephalosporanate
Reference
  Authors
Michal G.
  Title
Biochemical Pathways
  Journal
Wiley (1999)
Related
pathway
rn00310  Lysine degradation
KO pathway
ko00311   

DBGET integrated database retrieval system