Entry Name Streptomycin biosynthesis - Gemmata massiliana
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 metabolitesBRITE hierarchy
Pathway map Ortholog table Module Other DBs Organism Gemmata massiliana [GN:
gms ]
Gene SOIL9_18530 ROK family protein OS=Isosphaera pallida (strain ATCC 43644 / DSM 9630 / IS1B) GN=Isop_2979 PE=4 SV=1: ROK [KO:K25026 ] [EC:2.7.1.2 ]
SOIL9_83660 glucokinase xylose repressor : Transcriptional regulator/sugar kinase OS=Singulisphaera acidiphila (strain ATCC BAA-1392 / DSM 18658 / VKM B-2454 / MOB10) GN=Sinac_6144 PE=4 SV=1: ROK [KO:K25026 ] [EC:2.7.1.2 ]
SOIL9_18500 Transcriptional regulator/sugar kinase OS=Singulisphaera acidiphila (strain ATCC BAA-1392 / DSM 18658 / VKM B-2454 / MOB10) GN=Sinac_2932 PE=4 SV=1: ROK [KO:K25026 ] [EC:2.7.1.2 ]
SOIL9_08810 phosphoglucomutase : Phosphoglucomutase OS=Rhodovulum sp. PH10 GN=A33M_3475 PE=3 SV=1: PGM_PMM_I: PGM_PMM_II: PGM_PMM_III: PGM_PMM_IV [KO:K01835 ] [EC:5.4.2.2 ]
SOIL9_23680 phosphoglucomutase : Phosphoglucomutase OS=Rhodovulum sp. PH10 GN=A33M_3475 PE=3 SV=1: PGM_PMM_I: PGM_PMM_II: PGM_PMM_III: PGM_PMM_IV [KO:K01835 ] [EC:5.4.2.2 ]
SOIL9_27840 phosphoglucomutase : Uncharacterized protein OS=Candidatus Entotheonella sp. TSY2 GN=ETSY2_36385 PE=4 SV=1: PGM_PMM_I: PGM_PMM_II: PGM_PMM_III [KO:K01835 ] [EC:5.4.2.2 ]
SOIL9_06780 myo-inositol-1-phosphate synthase : Myo-inositol-1-phosphate synthase OS=Pirellula staleyi (strain ATCC 27377 / DSM 6068 / ICPB 4128) GN=Psta_3018 PE=4 SV=1: NAD_binding_5: Inos-1-P_synth [KO:K01858 ] [EC:5.5.1.4 ]
SOIL9_66500 inositol-1-monophosphatase : Inositol monophosphatase OS=Planctomyces brasiliensis (strain ATCC 49424 / DSM 5305 / JCM 21570 / NBRC 103401 / IFAM 1448) GN=Plabr_4686 PE=4 SV=1: Inositol_P [KO:K01092 ] [EC:3.1.3.25 ]
SOIL9_11410 dehydrogenase : Oxidoreductase domain protein OS=Isosphaera pallida (strain ATCC 43644 / DSM 9630 / IS1B) GN=Isop_2477 PE=4 SV=1: GFO_IDH_MocA [KO:K00010 ] [EC:1.1.1.18 1.1.1.369 ]
SOIL9_82930 spore coat protein : Marine sediment metagenome DNA, contig: S06H3_S06419 OS=marine sediment metagenome GN=S06H3_34823 PE=4 SV=1: NTP_transferase [KO:K00973 ] [EC:2.7.7.24 ]
SOIL9_72580 nad-dependent dehydratase : NAD-dependent epimerase/dehydratase OS=Rhodothermus marinus (strain ATCC 43812 / DSM 4252 / R-10) GN=Rmar_1858 PE=4 SV=1: Epimerase [KO:K01710 ] [EC:4.2.1.46 ]
SOIL9_82940 spore coat protein : dTDP-glucose 4,6-dehydratase OS=Planctomyces maris DSM 8797 GN=PM8797T_31915 PE=3 SV=1: Epimerase [KO:K01710 ] [EC:4.2.1.46 ]
SOIL9_38270 dtdp-glucose -dehydratase : Marine sediment metagenome DNA, contig: S01H1_L05958 OS=marine sediment metagenome GN=S01H1_14926 PE=4 SV=1: Epimerase [KO:K01710 ] [EC:4.2.1.46 ]
SOIL9_49970 dtdp-4-dehydrorhamnose -epimerase : dTDP-4-dehydrorhamnose 3,5-epimerase OS=Crinalium epipsammum PCC 9333 GN=Cri9333_3401 PE=4 SV=1: dTDP_sugar_isom [KO:K01790 ] [EC:5.1.3.13 ]
SOIL9_26660 dtdp-4-dehydrorhamnose -epimerase : dTDP-4-dehydrorhamnose 35-epimerase related protein OS=Geobacter sp. (strain M18) GN=GM18_2321 PE=4 SV=1: dTDP_sugar_isom [KO:K01790 ] [EC:5.1.3.13 ]
SOIL9_41760 dTDP-4-dehydrorhamnose reductase OS=uncultured planctomycete GN=HGMM_F01A04C04 PE=4 SV=1: RmlD_sub_bind [KO:K00067 ] [EC:1.1.1.133 ]
Compound C00688 dTDP-4-dehydro-beta-L-rhamnose
C00691 2,4,6/3,5-Pentahydroxycyclohexanone
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
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 Reference Authors Flatt PM, Mahmud T
Title Biosynthesis of aminocyclitol-aminoglycoside antibiotics and related compounds.
Journal Reference Authors Walker JB
Title Possible evolutionary relationships between streptomycin and bluensomycin biosynthetic pathways: detection of novel inositol kinase and O-carbamoyltransferase activities.
Journal Reference 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 Reference 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 Reference Authors Distler J, Mansouri K, Mayer G, Stockmann M, Piepersberg W
Title Streptomycin biosynthesis and its regulation in Streptomycetes.
Journal Reference Authors Mansouri K, Piepersberg W.
Title Genetics of streptomycin production in Streptomyces griseus: nucleotide sequence of five genes, strFGHIK, including a phosphatase gene.
Journal Reference 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 Related gms00523 Polyketide sugar unit biosynthesis
KO pathway LinkDB All DBs
