Entry Name Monobactam biosynthesis - Prauserella marina
Description Monobactams are beta-lactam antibiotics containing a monocyclic beta-lactam nucleus, which is structurally different from penicillin and cephalosporin core structures with another fused ring. This diagram shows biosynthesis of nocardicin A, a naturally occurring monobactam, via the pentapeptide formed by condensation of L-4-hydroxyphenylglycine (L-pHPG), L-arginine and L-serine [MD:
M00736 ]. Other naturally occurring monobactams are also shown but the biosynthetic pathway is not yet fully characterized. Sulfazecin and other 3-aminomonobactamic acid derivatives are derived from serine or threonine, and tabtoxinine-beta-lactam is a phytotoxin. Aztreonam, a synthetic monobactam originally isolated as SQ 26,180 from Chromobacterium violaceum, is the first clinically used monobactam.
Class Metabolism; Biosynthesis of other secondary metabolitesBRITE hierarchy
Pathway map Ortholog table Organism Prauserella marina [GN:
pmad ]
Gene Compound C00019 S-Adenosyl-L-methionine
C00441 L-Aspartate 4-semialdehyde
C01179 3-(4-Hydroxyphenyl)pyruvate
C03590 4-Hydroxyphenylglyoxylate
C03972 2,3,4,5-Tetrahydrodipicolinate
C05539 N-Acetyl-L-2-amino-6-oxopimelate
C12323 L-4-Hydroxyphenylglycine
C20258 (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
C20918 Tabtoxinine-beta-lactam
C20920 Tabtoxinine-delta-lactam
C20921 N1-Acetyl-tabtoxinine-beta-lactam
C20929 3alpha-Hydroxy-3-aminoacylmonobactamic acid
Reference Authors Hamed RB, Gomez-Castellanos JR, Henry L, Ducho C, McDonough MA, Schofield CJ
Title The enzymes of beta-lactam biosynthesis.
Journal Reference Authors Gunsior M, Breazeale SD, Lind AJ, Ravel J, Janc JW, Townsend CA
Title The biosynthetic gene cluster for a monocyclic beta-lactam antibiotic, nocardicin A.
Journal Reference Authors Kelly WL, Townsend CA
Title Mutational analysis and characterization of nocardicin C-9' epimerase.
Journal Reference Authors Kelly WL, Townsend CA
Title Mutational analysis of nocK and nocL in the nocardicin a producer Nocardia uniformis.
Journal Reference Authors Reeve AM, Breazeale SD, Townsend CA
Title Purification, characterization, and cloning of an S-adenosylmethionine-dependent 3-amino-3-carboxypropyltransferase in nocardicin biosynthesis.
Journal Reference Authors Kelly WL, Townsend CA
Title Role of the cytochrome P450 NocL in nocardicin A biosynthesis.
Journal Reference Authors Hubbard BK, Thomas MG, Walsh CT
Title Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics.
Journal Reference Authors Gaudelli NM, Long DH, Townsend CA
Title beta-Lactam formation by a non-ribosomal peptide synthetase during antibiotic biosynthesis.
Journal Reference Authors Gaudelli NM, Townsend CA
Title Epimerization and substrate gating by a TE domain in beta-lactam antibiotic biosynthesis.
Journal Reference Authors Davidsen JM, Townsend CA
Title In vivo characterization of nonribosomal peptide synthetases NocA and NocB in the biosynthesis of nocardicin A.
Journal Reference Authors Davidsen JM, Bartley DM, Townsend CA
Title Non-ribosomal propeptide precursor in nocardicin A biosynthesis predicted from adenylation domain specificity dependent on the MbtH family protein NocI.
Journal Reference Authors O'Sullivan J, Gillum AM, Aklonis CA, Souser ML, Sykes RB
Title Biosynthesis of monobactam compounds: origin of the carbon atoms in the beta-lactam ring.
Journal Reference Authors O'Sullivan J, Souser ML, Kao CC, Aklonis CA
Title Sulfur metabolism in the biosynthesis of monobactams.
Journal Reference Authors Kinscherf TG, Willis DK
Title The biosynthetic gene cluster for the beta-lactam antibiotic tabtoxin in Pseudomonas syringae.
Journal Reference Authors Wencewicz TA, Walsh CT
Title Pseudomonas syringae self-protection from tabtoxinine-beta-lactam by ligase TblF and acetylase Ttr.
Journal Reference Authors Arai T, Arimura Y, Ishikura S, Kino K
Title L-amino acid ligase from Pseudomonas syringae producing tabtoxin can be used for enzymatic synthesis of various functional peptides.
Journal Reference Authors Engst K, Shaw PD
Title Identification of a lysA-like gene required for tabtoxin biosynthesis and pathogenicity in Pseudomonas syringae pv. tabaci strain PTBR2.024.
Journal Reference Authors Liu L, Shaw PD
Title Characterization of dapB, a gene required by Pseudomonas syringae pv. tabaci BR2.024 for lysine and tabtoxinine-beta-lactam biosynthesis.
Journal Reference Authors Liu L, Shaw PD
Title A possible role for acetylated intermediates in diaminopimelate and tabtoxinine-beta-lactam biosynthesis in Pseudomonas syringae pv. tabaci BR2.024.
Journal Reference Authors Unkefer CJ, London RE, Durbin RD, Uchytil TF, Langston-Unkefer PJ
Title The biosynthesis of tabtoxinine-beta-lactam. Use of specifically 13C-labeled glucose and 13C NMR spectroscopy to identify its biosynthetic precursors.
Journal J Biol Chem 262:4994-9 (1987)
Related pmad00250 Alanine, aspartate and glutamate metabolism
pmad00260 Glycine, serine and threonine metabolism
pmad00400 Phenylalanine, tyrosine and tryptophan biosynthesis
KO pathway LinkDB All DBs
