KEGG   PATHWAY: sma00521
Entry
sma00521                    Pathway                                
Name
Streptomycin biosynthesis - Streptomyces avermitilis
Description
Streptomycin is an aminocyclitol-aminoglycoside antibiotic produced by Streptomyces griseus. Streptomycin consists of aminocyclitol (streptidine), 6-deoxyhexose (streptose), and N-methyl-L-glucosamine moieties, which are formed by independent biosynthetic pathways. All of the moieties are derived from D-glucose. The streptidine moiety is synthesized via myo-inositol, which is then oxidized at C-1 and transaminated to give scyllo-inosamine. After phosphorylation, the compound is transamidinated by arginine. The same procedure is repeated at the C-3 position. The streptose moiety is made from D-glucose via a dTDP-glucose pathway. The exact biosynthetic route for the N-methyl-L-glucosamine moiety is unknown, though the biosynthetic gene cluster have been proposed.
Class
Metabolism; Biosynthesis of other secondary metabolites
Pathway map
sma00521  Streptomycin biosynthesis
sma00521

Other DBs
GO: 0019872
Organism
Streptomyces avermitilis [GN:sma]
Gene
SAVERM_6074  glkA1; glucokinase [KO:K25026] [EC:2.7.1.2]
SAVERM_1476  putative ROK-family transcriptional regulator [KO:K25026] [EC:2.7.1.2]
SAVERM_3940  putative ROK-family transcriptional regulator [KO:K25026] [EC:2.7.1.2]
SAVERM_1980  putative carbohydrate kinase [KO:K25026] [EC:2.7.1.2]
SAVERM_803  pgmA; putative phosphoglucomutase [KO:K01835] [EC:5.4.2.2]
SAVERM_4296  ino1; 1L-myo-inositol-1-phosphate synthase [KO:K01858] [EC:5.5.1.4]
SAVERM_2406  suhB1; putative myo-inositol 1-monophosphatase [KO:K01092] [EC:3.1.3.25]
SAVERM_372  suhB2; putative myo-inositol 1-monophosphatase [KO:K01092] [EC:3.1.3.25]
SAVERM_1234  iolG1; putative myo-inositol 2-dehydrogenase [KO:K00010] [EC:1.1.1.18 1.1.1.369]
SAVERM_7188  iolG2; myo-inositol 2-dehydrogenase [KO:K00010] [EC:1.1.1.18 1.1.1.369]
SAVERM_1985  putative oxidoreductase [KO:K00010] [EC:1.1.1.18 1.1.1.369]
SAVERM_947  aveBIII; glucose-1-phosphate thymidyltransferase [KO:K00973] [EC:2.7.7.24]
SAVERM_946  aveBII; dTDP-glucose 4,6-dehydratase [KO:K01710] [EC:4.2.1.46]
Compound
C00031  D-Glucose
C00092  D-Glucose 6-phosphate
C00103  D-Glucose 1-phosphate
C00137  myo-Inositol
C00413  Streptomycin
C00688  dTDP-4-dehydro-beta-L-rhamnose
C00691  2,4,6/3,5-Pentahydroxycyclohexanone
C00842  dTDP-glucose
C01121  Streptidine 6-phosphate
C01138  Streptomycin 6-phosphate
C01214  1-Amino-1-deoxy-scyllo-inositol
C01221  Dihydrostreptomycin 6-phosphate
C01283  1-Amino-1-deoxy-scyllo-inositol 4-phosphate
C01294  1-Guanidino-1-deoxy-scyllo-inositol 4-phosphate
C01298  1D-1-Guanidino-3-amino-1,3-dideoxy-scyllo-inositol
C03319  dTDP-L-rhamnose
C03442  dTDP-L-dihydrostreptose
C04006  1D-myo-Inositol 3-phosphate
C04280  1-Guanidino-1-deoxy-scyllo-inositol
C04673  1D-1-Guanidino-1-deoxy-3-dehydro-scyllo-inositol
C04767  O-(1->4)-alpha-L-Dihydrostreptosyl-streptidine 6-phosphate
C06592  NDP-N-methyl-L-glucosamine
C11351  N1-Amidinostreptamine 6-phosphate
C11907  dTDP-4-oxo-6-deoxy-D-glucose
Reference
PMID:19362651
  Authors
Wehmeier UF, Piepersberg W
  Title
Enzymology of aminoglycoside biosynthesis-deduction from gene clusters.
  Journal
Methods Enzymol 459:459-91 (2009)
DOI:10.1016/S0076-6879(09)04619-9
Reference
PMID:17390001
  Authors
Flatt PM, Mahmud T
  Title
Biosynthesis of aminocyclitol-aminoglycoside antibiotics and related compounds.
  Journal
Nat Prod Rep 24:358-92 (2007)
DOI:10.1039/b603816f
Reference
PMID:1698764
  Authors
Walker JB
  Title
Possible evolutionary relationships between streptomycin and bluensomycin biosynthetic pathways: detection of novel inositol kinase and O-carbamoyltransferase activities.
  Journal
J Bacteriol 172:5844-51 (1990)
DOI:10.1128/JB.172.10.5844-5851.1990
Reference
PMID:2995326
  Authors
Ohnuki T, Imanaka T, Aiba S
  Title
Self-cloning in Streptomyces griseus of an str gene cluster for streptomycin biosynthesis and streptomycin resistance.
  Journal
J Bacteriol 164:85-94 (1985)
DOI:10.1128/JB.164.1.85-94.1985
Reference
PMID:9238101
  Authors
Ahlert J, Distler J, Mansouri K, Piepersberg W
  Title
Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes.
  Journal
Arch Microbiol 168:102-13 (1997)
DOI:10.1007/s002030050475
Reference
PMID:1377151
  Authors
Distler J, Mansouri K, Mayer G, Stockmann M, Piepersberg W
  Title
Streptomycin biosynthesis and its regulation in Streptomycetes.
  Journal
Gene 115:105-11 (1992)
DOI:10.1016/0378-1119(92)90547-3
Reference
PMID:1654502
  Authors
Mansouri K, Piepersberg W.
  Title
Genetics of streptomycin production in Streptomyces griseus: nucleotide sequence of five genes, strFGHIK, including a phosphatase gene.
  Journal
Mol Gen Genet 228:459-69 (1991)
DOI:10.1007/BF00260640
Reference
PMID:9922132
  Authors
Fritsche E, Bergner A, Humm A, Piepersberg W, Huber R
  Title
Crystal structure of L-arginine:inosamine-phosphate amidinotransferase StrB1 from Streptomyces griseus: an enzyme involved in streptomycin biosynthesis.
  Journal
Biochemistry 37:17664-72 (1998)
DOI:10.1021/bi981949p
Related
pathway
sma00523  Polyketide sugar unit biosynthesis
KO pathway
ko00521   

  All links  
Genome (1)   
   KEGG GENOME (1)   
Gene (13)   
   KEGG GENES (13)   
All databases (14)   

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