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   

  All links  
Genome (1)   
   KEGG GENOME (1)   
Gene (6)   
   KEGG GENES (6)   
All databases (7)   

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