KEGG   PATHWAY: map00521Help
Entry
map00521                    Pathway                                

Name
Streptomycin biosynthesis
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
BRITE hierarchy
Pathway map
map00521  Streptomycin biosynthesis
map00521

Ortholog table
Module
M00793  dTDP-L-rhamnose biosynthesis [PATH:map00521]
Drug
D08531  Streptomycin (INN)
Other DBs
GO: 0019872
Reference
  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
  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)
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
KO pathway
ko00521   

DBGET integrated database retrieval system