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Entry
bnc00521                    Pathway                                

Name
Streptomycin biosynthesis - Bacillus cereus NC7401
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
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Pathway map
Streptomycin biosynthesis
bnc00521

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BSID: 
GO: 
Organism
Bacillus cereus NC7401 [GN:bnc]
Gene
glucokinase; K00845 glucokinase [EC:2.7.1.2] [KO:K00845] [EC:2.7.1.2]
glucokinase; K00845 glucokinase [EC:2.7.1.2] [KO:K00845] [EC:2.7.1.2]
phosphoglucomutase/phosphomannomutase family protein; K01835 phosphoglucomutase [EC:5.4.2.2] [KO:K01835] [EC:5.4.2.2]
inositol monophosphatase family protein; K01092 myo-inositol-1(or 4)-monophosphatase [EC:3.1.3.25] [KO:K01092] [EC:3.1.3.25]
glucose-1-phosphate thymidylyltransferase; K00973 glucose-1-phosphate thymidylyltransferase [EC:2.7.7.24] [KO:K00973] [EC:2.7.7.24]
dTDP-glucose 4; K01710 dTDP-glucose 4,6-dehydratase [EC:4.2.1.46] [KO:K01710] [EC:4.2.1.46]
dTDP-4-dehydrorhamnose 3; K01790 dTDP-4-dehydrorhamnose 3,5-epimerase [EC:5.1.3.13] [KO:K01790] [EC:5.1.3.13]
dTDP-4-dehydrorhamnose reductase; K00067 dTDP-4-dehydrorhamnose reductase [EC:1.1.1.133] [KO:K00067] [EC:1.1.1.133]
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
  Authors
Wehmeier UF, Piepersberg W
  Title
Enzymology of aminoglycoside biosynthesis-deduction from gene clusters.
  Journal
Methods Enzymol 459:459-91 (2009)
Reference
  Authors
Flatt PM, Mahmud T
  Title
Biosynthesis of aminocyclitol-aminoglycoside antibiotics and related compounds.
  Journal
Nat Prod Rep 24:358-92 (2007)
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)
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)
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)
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)
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)
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)
KO pathway
 

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