KEGG   PATHWAY: sma00311Help
Entry
sma00311                    Pathway                                

Name
Penicillin and cephalosporin biosynthesis - Streptomyces avermitilis
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
BRITE hierarchy
Pathway map
sma00311  Penicillin and cephalosporin biosynthesis
sma00311

Ortholog table
Organism
Streptomyces avermitilis [GN:sma]
Gene
SAVERM_1302  axe1; putative acetyl xylan esterase [KO:K01060] [EC:3.1.1.41]
SAVERM_1457  axe2; putative acetyl xylan esterase [KO:K01060] [EC:3.1.1.41]
SAVERM_1672  dao; putative D-amino acid oxidase [KO:K00273] [EC:1.4.3.3]
SAVERM_3675  pacB1; putative penicillin acylase, secreted [KO:K01434] [EC:3.5.1.11]
SAVERM_4171  pacB2; putative penicillin acylase [KO:K01434] [EC:3.5.1.11]
SAVERM_4452  blaA3; putative beta-lactamase (ampC), secreted [KO:K17836] [EC:3.5.2.6]
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
sma00310  Lysine degradation
KO pathway
ko00311   

DBGET integrated database retrieval system