KEGG   PATHWAY: rn00998
Entry
rn00998                     Pathway                                
Name
Biosynthesis of various antibiotics
  Including
Kanosamine biosynthesis, Aurachin biosynthesis, Bacilysin biosynthesis, Puromycin biosynthesis, Dapdiamides biosynthesis, Fosfomycin biosynthesis, Cremeomycin biosynthesis, Pentalenolactone biosynthesis, Terpentecin biosynthesis, Roseoflavin biosynthesis, Cycloserine biosynthesis
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
rn00998  Biosynthesis of various antibiotics
rn00998

Module
M00785  Cycloserine biosynthesis, arginine/serine => cycloserine [PATH:rn00998]
M00787  Bacilysin biosynthesis, prephenate => bacilysin [PATH:rn00998]
M00788  Terpentecin biosynthesis, GGAP => terpentecin [PATH:rn00998]
M00819  Pentalenolactone biosynthesis, farnesyl-PP => pentalenolactone [PATH:rn00998]
M00848  Aurachin biosynthesis, anthranilate => aurachin A [PATH:rn00998]
M00877  Kanosamine biosynthesis, glucose 6-phosphate => kanosamine [PATH:rn00998]
M00889  Puromycin biosynthesis, ATP => puromycin [PATH:rn00998]
M00890  Roseoflavin biosynthesis, FMN => roseoflavin [PATH:rn00998]
M00903  Fosfomycin biosynthesis, phosphoenolpyruvate => fosfomycin [PATH:rn00998]
M00904  Dapdiamides biosynthesis, L-2,3-diaminopropanoate => dapdiamide A/B/C [PATH:rn00998]
Reaction
R00586  acetyl-CoA:L-serine O-acetyltransferase
R00661  phosphoenolpyruvate 2,3-phosphonomutase
R00982  Anthranilate:CoA ligase (AMP-forming)
R02305  2-trans,6-trans-farnesyldiphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
R04053  3-phosphonopyruvate carboxy-lyase
R05668   
R05669   
R05670   
R05671   
R05672   
R05673   
R05674   
R05675   
R05676   
R05677   
R08861   
R08863  (S)-2-hydroxypropylphosphonate,NADH:oxygen epoxidase
R09478  2-hydroxyethylphosphonate:NAD+ oxidoreductase
R09684  terpentedienyl-diphosphate diphosphate-lyase (terpentetriene-forming)
R09714  terpentedienyl-diphosphate lyase (decyclizing)
R09814  pentalenene,reduced ferredoxin:oxygen 13-oxidoreductase
R10145  pentalenolactone-D,2-oxoglutarate:oxygen oxidoreductase
R10154  1-deoxy-11-oxopentalenate,NADH:oxygen oxidoreductase (pentalenolactone-D forming)
R10155  1-deoxy-11-oxopentalenate,NADH:oxygen oxidoreductase (neopentalenolactone-D forming)
R10156  1-deoxy-11beta-hydroxypentalenate:NAD+ oxidoreductase
R10157  1-deoxypentalenic acid,2-oxoglutarate:oxygen oxidoreductase
R10158  1-deoxypentalenate,reduced ferredoxin:oxygen oxidoreductase
R10162  pentalenolactone-reduced-ferredoxin:oxygen oxidoreductase (pentalenolactone forming)
R10461  O-acetyl-L-serine:hydroxyurea 2-amino-2-carboxyethyltransferase
R10466  N(omega)-hydroxy-L-arginine amidinohydrolase
R10470  O-ureido-D-serine cyclo-ligase (D-cycloserine-forming)
R10488  (2S)-2-amino-3-[(carbamoylamino)oxy]propanoate 2-epimerase
R10519  D-glucose-6-phosphate:NAD+ oxidoreductase
R10547  kanosamine-6-phosphate phosphohydrolase
R10698  kanosamine-6-phosphate:2-oxoglutarate aminotransferase
R10917  L-dihydroanticapsin:NAD+ oxidoreductase
R10934  prephenate carboxy-lyase (3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate-forming)
R10940  fumarate:L-2,3-diaminopropanoate ligase (AMP-forming)
R10942  3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-valine ligase (ADP-forming)
R10943  3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-isoleucine ligase (ADP-forming)
R10944  3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-leucine ligase (ADP-forming)
R11033   
R11064  L-alanine:L-anticapsin ligase (ADP-forming)
R11065  3-[(4R)-4-hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate isomerase
R11066   
R11067   
R11068   
R11069   
R11149  aurachin B:NAD+ 3-oxidoreductase
R11315   
R11382  aurachin C:NADH:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
R11383  aurachin C:NADPH:oxygen oxidoreductase (4-hydroxy-2-methyl-3-oxo-4-farnesyl-3,4-dihydroquinoline-1-oxide-forming)
R11655  N-[(2S)-2-amino-2-carboxyethyl]-L-glutamate:NAD+ dehydrogenase (L-2,3-diaminopropanoate-forming)
R11705  O-phospho-L-serine:L-glutamate N-(2S)-2-amino-2-carboxyethyltransferase
R11779  S-adenosyl-L-methionine:8-amino-8-demethylriboflavin N-methyltransferase
R11780  S-adenosyl-L-methionine:8-demethyl-8-(methylamino)riboflavin N-methyltransferase
R11961   
R11962   
R11963   
R12049   
R12050   
R12051  aurachin-D,NADPH:oxygen oxidoreductase (N-hydroxylating)
R12052  aurachin-B,NADPH:oxygen oxidoreductase (2',3'-epoxidizing)
R12053  aurachin-B,NADH:oxygen oxidoreductase (2',3'-epoxidizing)
R12054   
R12114  8-amino-8-demethylriboflavin-5'-phosphate phosphohydrolase
R12352   
R12497  S-adenosyl-L-methionine:cytidine 5'-{[hydroxy(2-hydroxyethyl)phosphonoyl]phosphate} C-methyltransferase
R12498   
R12499   
R12907  L-aspartate,NADPH:oxygen oxidoreductase [(2S)-2-nitrobutanedioate-forming]
R12912  3-amino-4-hydroxybenzoate,NADPH:oxygen oxidoreductase (2-hydroxylating)
R12928  S-adenosyl-L-methionine:3-amino-4-hydroxybenzoate 4-O-methyltransferase
R12943  3-amino-2-hydroxy-4-methoxybenzoate:nitrite ligase (AMP-forming)
R12947  2-nitrobutanedioate lyase (fumarate-forming)
Compound
C00002  ATP
C00022  Pyruvate
C00024  Acetyl-CoA
C00025  L-Glutamate
C00026  2-Oxoglutarate
C00036  Oxaloacetate
C00049  L-Aspartate
C00061  FMN
C00062  L-Arginine
C00065  L-Serine
C00074  Phosphoenolpyruvate
C00077  L-Ornithine
C00082  L-Tyrosine
C00088  Nitrite
C00092  D-Glucose 6-phosphate
C00108  Anthranilate
C00129  Isopentenyl diphosphate
C00197  3-Phospho-D-glycerate
C00251  Chorismate
C00254  Prephenate
C00279  D-Erythrose 4-phosphate
C00353  Geranylgeranyl diphosphate
C00441  L-Aspartate 4-semialdehyde
C00448  trans,trans-Farnesyl diphosphate
C00979  O-Acetyl-L-serine
C01005  O-Phospho-L-serine
C01179  3-(4-Hydroxyphenyl)pyruvate
C01610  Puromycin
C01841  Pentalenene
C02247  Anthraniloyl-CoA
C02798  3-Phosphonopyruvate
C03167  Phosphonoacetaldehyde
C03401  L-2,3-Diaminopropanoate
C05345  beta-D-Fructose 6-phosphate
C05933  N(omega)-Hydroxyarginine
C06451  2-Hydroxyethylphosphonate
C06452  (S)-2-Hydroxypropylphosphonate
C06454  Fosfomycin
C07024  3'-Keto-3'-deoxy-ATP
C07025  3'-Keto-3'-deoxy-AMP
C07026  3'-Amino-3'-deoxy-AMP
C07027  N6,N6,O-Tridemethylpuromycin-5'-phosphate
C07028  N-Acetyl-N6,N6,O-tridemethylpuromycin-5'-phosphate
C07029  N-Acetyl-N6,O-didemethylpuromycin-5'-phosphate
C07030  N-Acetyl-O-demethylpuromycin-5'-phosphate
C07031  N-Acetyl-O-demethylpuromycin
C07032  N-Acetylpuromycin
C07044  Hydroxyurea
C08057  Cycloserine
C10641  Aurachin D
C12115  3-Amino-4-hydroxybenzoate
C12212  Kanosamine
C12213  Kanosamine 6-phosphate
C19814  Terpentetriene
C19815  Terpentedienyl diphosphate
C19939  Pentalen-13-al
C20397  Pentalenolactone F
C20399  Pentalenolactone D
C20400  1-Deoxy-11-oxopentalenate
C20402  Neopentalenolactone D
C20403  1-Deoxy-11beta-hydroxypentalenate
C20404  1-Deoxypentalenate
C20405  Pentalenate
C20407  Pentalenolactone
C20639  O-Ureido-L-serine
C20651  O-Ureido-D-serine
C20668  3-Dehydro-D-glucose 6-phosphate
C20940  L-Dihydroanticapsin
C20941  L-Anticapsin
C20942  Bacilysin
C20953  3-[(4R)-4-Hydroxycyclohexa-1,5-dien-1-yl]-2-oxopropanoate
C20961  N3-Fumaroyl-L-2,3-diaminopropanoate
C20962  Dapdiamide A
C20963  Dapdiamide B
C20964  Dapdiamide C
C20966  3-{[(2E)-4-Amino-4-oxobut-2-enoyl]amino}-L-alanine
C21085  3-[(1E,4R)-4-Hydroxycyclohex-2-en-1-ylidene]-2-oxopropanoate
C21086  (3E)-3-[(1R,5R,6S)-5-Hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylidene]-2-oxopropanoate
C21087  3-[(1R,2S,5R,6S)-5-Hydroxy-7-oxabicyclo[4.1.0]heptan-2-yl]-2-oxopropanoate
C21093  Terpentecin
C21140  Aurachin B
C21141  4-Hydroxy-2-methyl-3-oxo-4-[(2E,6E)-farnesyl]-3,4-dihydroquinoline 1-oxide
C21330  Aurachin C
C21559  N-[(2S)-2-Amino-2-carboxyethyl]-L-glutamate
C21646  8-Amino-8-demethylriboflavin
C21647  Roseoflavin
C21648  8-Demethyl-8-(methylamino)riboflavin
C21803  8-Demethyl-8-formylriboflavin 5'-phosphate
C21804  8-Carboxy-8-demethylriboflavin 5'-phosphate
C21805  8-Amino-8-demethylriboflavin 5'-phosphate
C21873  2-Methylquinolin-4-ol
C21874  Aurachin B epoxide
C21875  Aurachin A
C22216  Cytidine 5'-{[hydroxy(2-hydroxyethyl)phosphonoyl]phosphate}
C22217  Cytidine 5'-{[hydroxy(2-hydroxypropyl)phosphonoyl]phosphate}
C22388  (2S)-2-Nitrobutanedioate
C22416  Cremeomycin
C22425  3-Amino-2-hydroxy-4-methoxybenzoate
C22455  3-Amino-2,4-dihydroxybenzoate
Reference
  Authors
Sandmann A, Dickschat J, Jenke-Kodama H, Kunze B, Dittmann E, Muller R
  Title
A Type II polyketide synthase from the gram-negative Bacterium Stigmatella aurantiaca is involved in Aurachin alkaloid biosynthesis.
  Journal
Angew Chem Int Ed Engl 46:2712-6 (2007)
DOI:10.1002/anie.200603513
Reference
  Authors
Vetter ND, Langill DM, Anjum S, Boisvert-Martel J, Jagdhane RC, Omene E, Zheng H, van Straaten KE, Asiamah I, Krol ES, Sanders DA, Palmer DR
  Title
A previously unrecognized kanosamine biosynthesis pathway in Bacillus subtilis.
  Journal
J Am Chem Soc 135:5970-3 (2013)
DOI:10.1021/ja4010255
Reference
  Authors
Ozcengiz G, Ogulur I
  Title
Biochemistry, genetics and regulation of bacilysin biosynthesis and its significance more than an antibiotic.
  Journal
N Biotechnol 32:612-9 (2015)
DOI:10.1016/j.nbt.2015.01.006
Reference
PMID:8576156
  Authors
Tercero JA, Espinosa JC, Lacalle RA, Jimenez A.
  Title
The biosynthetic pathway of the aminonucleoside antibiotic puromycin, as deduced from the molecular analysis of the pur cluster of Streptomyces alboniger.
  Journal
J Biol Chem 271:1579-90 (1996)
DOI:10.1074/jbc.271.3.1579
Reference
  Authors
Hollenhorst MA, Clardy J, Walsh CT
  Title
The ATP-dependent amide ligases DdaG and DdaF assemble the fumaramoyl-dipeptide scaffold of the dapdiamide antibiotics.
  Journal
Biochemistry 48:10467-72 (2009)
DOI:10.1021/bi9013165
Reference
  Authors
Schwarz J, Konjik V, Jankowitsch F, Sandhoff R, Mack M
  Title
Identification of the Key Enzyme of Roseoflavin Biosynthesis.
  Journal
Angew Chem Int Ed Engl 55:6103-6 (2016)
DOI:10.1002/anie.201600581
Reference
  Authors
Kumagai T, Koyama Y, Oda K, Noda M, Matoba Y, Sugiyama M
  Title
Molecular cloning and heterologous expression of a biosynthetic gene cluster for the antitubercular agent D-cycloserine produced by Streptomyces lavendulae.
  Journal
Antimicrob Agents Chemother 54:1132-9 (2010)
DOI:10.1128/AAC.01226-09
Reference
  Authors
Hamano Y, Kuzuyama T, Itoh N, Furihata K, Seto H, Dairi T
  Title
Functional analysis of eubacterial diterpene cyclases responsible for biosynthesis of a diterpene antibiotic, terpentecin.
  Journal
J Biol Chem 277:37098-104 (2002)
DOI:10.1074/jbc.M206382200
Reference
  Authors
Quaderer R, Omura S, Ikeda H, Cane DE
  Title
Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis.
  Journal
J Am Chem Soc 128:13036-7 (2006)
DOI:10.1021/ja0639214
Reference
PMID:7500951
  Authors
Hidaka T, Goda M, Kuzuyama T, Takei N, Hidaka M, Seto H
  Title
Cloning and nucleotide sequence of fosfomycin biosynthetic genes of Streptomyces wedmorensis.
  Journal
Mol Gen Genet 249:274-80 (1995)
DOI:10.1007/BF00290527
Related
pathway
rn00010  Glycolysis / Gluconeogenesis
rn00020  Citrate cycle (TCA cycle)
rn00030  Pentose phosphate pathway
rn00220  Arginine biosynthesis
rn00250  Alanine, aspartate and glutamate metabolism
rn00260  Glycine, serine and threonine metabolism
rn00400  Phenylalanine, tyrosine and tryptophan biosynthesis
rn00440  Phosphonate and phosphinate metabolism
rn00900  Terpenoid backbone biosynthesis
KO pathway
ko00998   

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