ENTRY       sly00261                    Pathway
NAME        Monobactam biosynthesis - Solanum lycopersicum (tomato)
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 metabolites
PATHWAY_MAP sly00261  Monobactam biosynthesis
ORGANISM    Solanum lycopersicum (tomato) [GN:sly]
GENE        101256557  ATP sulfurylase 1, chloroplastic [KO:K13811] [EC:2.7.7.4 2.7.1.25]
            101259979  ATP sulfurylase 1, chloroplastic-like [KO:K13811] [EC:2.7.7.4 2.7.1.25]
            101256255  ATP sulfurylase 1, chloroplastic-like [KO:K13811] [EC:2.7.7.4 2.7.1.25]
            101258399  aspartokinase 2, chloroplastic isoform X2 [KO:K00928] [EC:2.7.2.4]
            101258465  bifunctional aspartokinase/homoserine dehydrogenase 1, chloroplastic [KO:K12524] [EC:2.7.2.4 1.1.1.3]
            101264587  bifunctional aspartokinase/homoserine dehydrogenase, chloroplastic-like [KO:K12524] [EC:2.7.2.4 1.1.1.3]
            101258686  uncharacterized protein LOC101258686 [KO:K00133] [EC:1.2.1.11]
            101250089  4-hydroxy-tetrahydrodipicolinate synthase, chloroplastic-like [KO:K01714] [EC:4.3.3.7]
            101250558  4-hydroxy-tetrahydrodipicolinate synthase, chloroplastic isoform X2 [KO:K01714] [EC:4.3.3.7]
            101253321  4-hydroxy-tetrahydrodipicolinate reductase 1, chloroplastic-like [KO:K00215] [EC:1.17.1.8]
COMPOUND    C00019  S-Adenosyl-L-methionine
            C00022  Pyruvate
            C00049  L-Aspartate
            C00059  Sulfate
            C00062  L-Arginine
            C00065  L-Serine
            C00082  L-Tyrosine
            C00188  L-Threonine
            C00224  Adenylyl sulfate
            C00441  L-Aspartate 4-semialdehyde
            C00927  Isonocardicin A
            C01179  3-(4-Hydroxyphenyl)pyruvate
            C01739  Nocardicin E
            C01941  Nocardicin A
            C03082  4-Phospho-L-aspartate
            C03198  (S)-4-Hydroxymandelate
            C03590  4-Hydroxyphenylglyoxylate
            C03972  2,3,4,5-Tetrahydrodipicolinate
            C05539  N-Acetyl-L-2-amino-6-oxopimelate
            C12323  L-4-Hydroxyphenylglycine
            C16842  SQ 26180
            C17351  Nocardicin C
            C17352  Isonocardicin C
            C17355  Nocardicin G
            C20258  (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate
            C20911  C20911
            C20912  C20912
            C20913  C20913
            C20914  C20914
            C20915  C20915
            C20916  C20916
            C20917  Tabtoxin
            C20918  Tabtoxinine-beta-lactam
            C20919  Isotabtoxin
            C20920  Tabtoxinine-delta-lactam
            C20921  N1-Acetyl-tabtoxinine-beta-lactam
            C20927  Sulfazecin
            C20928  MM 42842
            C20929  3alpha-Hydroxy-3-aminoacylmonobactamic acid
REFERENCE   PMID:23135477
  AUTHORS   Hamed RB, Gomez-Castellanos JR, Henry L, Ducho C, McDonough MA, Schofield CJ
  TITLE     The enzymes of beta-lactam biosynthesis.
  JOURNAL   Nat Prod Rep 30:21-107 (2013)
            DOI:10.1039/c2np20065a
REFERENCE   PMID:15271351
  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   Chem Biol 11:927-38 (2004)
            DOI:10.1016/j.chembiol.2004.04.012
REFERENCE   PMID:15252031
  AUTHORS   Kelly WL, Townsend CA
  TITLE     Mutational analysis and characterization of nocardicin C-9' epimerase.
  JOURNAL   J Biol Chem 279:38220-7 (2004)
            DOI:10.1074/jbc.M405450200
REFERENCE   PMID:15629944
  AUTHORS   Kelly WL, Townsend CA
  TITLE     Mutational analysis of nocK and nocL in the nocardicin a producer Nocardia uniformis.
  JOURNAL   J Bacteriol 187:739-46 (2005)
            DOI:10.1128/JB.187.2.739-746.2005
REFERENCE   PMID:9804844
  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   J Biol Chem 273:30695-703 (1998)
            DOI:10.1074/jbc.273.46.30695
REFERENCE   PMID:12105888
  AUTHORS   Kelly WL, Townsend CA
  TITLE     Role of the cytochrome P450 NocL in nocardicin A biosynthesis.
  JOURNAL   J Am Chem Soc 124:8186-7 (2002)
            DOI:10.1021/ja025926g
REFERENCE   PMID:11137816
  AUTHORS   Hubbard BK, Thomas MG, Walsh CT
  TITLE     Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics.
  JOURNAL   Chem Biol 7:931-42 (2000)
            DOI:10.1016/S1074-5521(00)00043-0
REFERENCE   PMID:25624104
  AUTHORS   Gaudelli NM, Long DH, Townsend CA
  TITLE     beta-Lactam formation by a non-ribosomal peptide synthetase during antibiotic biosynthesis.
  JOURNAL   Nature 520:383-7 (2015)
            DOI:10.1038/nature14100
REFERENCE   PMID:24531841
  AUTHORS   Gaudelli NM, Townsend CA
  TITLE     Epimerization and substrate gating by a TE domain in beta-lactam antibiotic biosynthesis.
  JOURNAL   Nat Chem Biol 10:251-8 (2014)
            DOI:10.1038/nchembio.1456
REFERENCE   PMID:22365611
  AUTHORS   Davidsen JM, Townsend CA
  TITLE     In vivo characterization of nonribosomal peptide synthetases NocA and NocB in the biosynthesis of nocardicin A.
  JOURNAL   Chem Biol 19:297-306 (2012)
            DOI:10.1016/j.chembiol.2011.10.020
REFERENCE   PMID:23330869
  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   J Am Chem Soc 135:1749-59 (2013)
            DOI:10.1021/ja307710d
REFERENCE   PMID:6805424
  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   Antimicrob Agents Chemother 21:558-64 (1982)
            DOI:10.1128/AAC.21.4.558
REFERENCE   PMID:6859838
  AUTHORS   O'Sullivan J, Souser ML, Kao CC, Aklonis CA
  TITLE     Sulfur metabolism in the biosynthesis of monobactams.
  JOURNAL   Antimicrob Agents Chemother 23:598-602 (1983)
            DOI:10.1128/AAC.23.4.598
REFERENCE   PMID:16506699
  AUTHORS   Kinscherf TG, Willis DK
  TITLE     The biosynthetic gene cluster for the beta-lactam antibiotic tabtoxin in Pseudomonas syringae.
  JOURNAL   J Antibiot (Tokyo) 58:817-21 (2005)
            DOI:10.1038/ja.2005.109
REFERENCE   PMID:22994681
  AUTHORS   Wencewicz TA, Walsh CT
  TITLE     Pseudomonas syringae self-protection from tabtoxinine-beta-lactam by ligase TblF and acetylase Ttr.
  JOURNAL   Biochemistry 51:7712-25 (2012)
            DOI:10.1021/bi3011384
REFERENCE   PMID:23770908
  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   Appl Environ Microbiol 79:5023-9 (2013)
            DOI:10.1128/AEM.01003-13
REFERENCE   PMID:1515668
  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   Mol Plant Microbe Interact 5:322-9 (1992)
            DOI:10.1094/mpmi-5-322
REFERENCE   PMID:8990304
  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   J Bacteriol 179:507-13 (1997)
            DOI:10.1128/JB.179.2.507-513.1997
REFERENCE   PMID:9294453
  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   J Bacteriol 179:5922-7 (1997)
            DOI:10.1128/JB.179.18.5922-5927.1997
REFERENCE   PMID:2881927
  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)
REL_PATHWAY sly00250  Alanine, aspartate and glutamate metabolism
            sly00260  Glycine, serine and threonine metabolism
            sly00300  Lysine biosynthesis
            sly00400  Phenylalanine, tyrosine and tryptophan biosynthesis
KO_PATHWAY  ko00261
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