KEGG   PATHWAY: rn00523
Entry
rn00523                     Pathway                                

Name
Polyketide sugar unit biosynthesis
Class
Metabolism; Metabolism of terpenoids and polyketides
Pathway map
rn00523  Polyketide sugar unit biosynthesis
rn00523

Module
M00793  dTDP-L-rhamnose biosynthesis [PATH:rn00523]
M00794  dTDP-6-deoxy-D-allose biosynthesis [PATH:rn00523]
M00795  dTDP-beta-L-noviose biosynthesis [PATH:rn00523]
M00796  dTDP-D-mycaminose biosynthesis [PATH:rn00523]
M00797  dTDP-D-desosamine biosynthesis [PATH:rn00523]
M00798  dTDP-L-mycarose biosynthesis [PATH:rn00523]
M00799  dTDP-L-oleandrose biosynthesis [PATH:rn00523]
M00800  dTDP-L-megosamine biosynthesis [PATH:rn00523]
M00801  dTDP-L-olivose biosynthesis [PATH:rn00523]
M00802  dTDP-D-forosamine biosynthesis [PATH:rn00523]
M00803  dTDP-D-angolosamine biosynthesis [PATH:rn00523]
Reaction
R02328  dTTP:alpha-D-glucose-1-phosphate thymidylyltransferase
R02773  dTDP-4-amino-4,6-dideoxy-D-glucose:2-oxoglutarate aminotransferase
R02776  dTDP-6-deoxy-L-talose:NADP+ 4-oxidoreductase
R02777  dTDP-beta-L-rhamnose:NADP+ 4-oxidoreductase
R05518  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose hydro-lyase (dTDP-2,6-dideoxy-D-glycero-hex-2-enos-4-ulose-forming)
R05526  dTDP-4-oxo-2,6-dideoxy-D-glucose:NADP+ 3-oxidoreductase
R05687  dTDP-4-keto-6-Deoxyglucose reductase
R06423  dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose:2-oxoglutarate aminotransferase
R06424  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose:dTDP-3-dehydro-6-deoxy-alpha-D-glucopyranose isomerase
R06426  dTDP-3-amino-3,4,6-trideoxy-D-glucose:2-oxoglutarate aminotransferase
R06427  S-adenosyl-L-methionine:dTDP-3-amino-3,4,6-trideoxy-alpha-D-glucopyranose 3-N,N-dimethyltransferase
R06433  dTDP-4-oxo-2,6-dideoxy-D-allose 5-epimerase
R06434   
R06436  dTDP-L-mycarose:NADP+ 4-oxidoreductase
R06437  dTDP-4-dehydro-6-deoxy-alpha-D-glucose 3-epimerase
R06438  dTDP-6-deoxy-alpha-D-allose:NAD+ oxidoreductase
R06439  S-adenosyl-L-methionine:dTDP-3-amino-3,6-dideoxy-alpha-D-glucopyranose 3-N,N-dimethyltransferase
R06443   
R06513  dTDPglucose 4,6-hydro-lyase
R06514  dTDP-4-dehydro-6-deoxy-alpha-D-glucose 3,5-epimerase
R06631  dTDP-3-amino-2,3,6-trideoxy-4-keto-D-glucose:2-oxoglutarate aminotransferase
R08583  dTDP-4-amino-4,6-dideoxy-D-glucose ammonia-lyase (dTDP-3-oxo-4,6-dideoxy-D-glucose-forming)
R08597  dTDP-4-oxo-2,6-dideoxy-D-glucose 3,5-epimerase
R08927   
R08928   
R08929   
R08930  dTDP-4-dehydro-2,6-dideoxy-alpha-D-glucose hydro-lyase (dTDP-2,3,6-trideoxy-alpha-D-hexopyranose-forming)
R08931  dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose:2-oxoglutarate aminotransferase
R08932  S-adenosyl-L-methionine:dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose N,N-dimethyltransferase
R08933  S-adenosyl-L-methionine:dTDP-4-oxo-2,6-dideoxy-D-allose 3-C-methyltransferase
R08934  dTDP-3-methyl-4-oxo-2,6-dideoxy-D-glucose 5-epimerase
R08935  dTDP-6-deoxy-L-mannose:NADP+ 4-oxidoreductase (3,5-epimerizing)
R09821  S-adenosyl-L-methionine:dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose 3-N,N-dimethyltransferase
R09824  dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose:2-oxoglutarate aminotransferase
R09873  acetyl-CoA:dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose 3-N-acetyltransferase
R09904  dTDP-4-dehydro-6-deoxy-alpha-D-glucopyranose:dTDP-3-dehydro-6-deoxy-alpha-D-galactopyranose isomerase
R10190  dTDP-6-deoxy-beta-L-talose:NAD+ 4-oxidoreductase
R10279  dTDP-6-deoxy-beta-L-talose 4-epimerase
R10459  dTDP-5-dimethyl-L-lyxose:NAD+ 4-oxidoreductase
R10536  dTDP-alpha-D-fucopyranose furanomutase
R10573  dTDP-6-deoxy-alpha-D-allose:NADP+ oxidoreductase
R11020  S-adenosyl-L-methionine:dTDP-4-oxo-6-deoxy-D-allose 5-C-methyltransferase
R11041  S-adenosyl-L-methionine:dTDP-4-oxo-2,6-dideoxy-L-mannose 3-O-methyltransferase
R11042   
R11045  S-adenosyl-L-methionine:dTDP-3-amino-2,3,6-trideoxy-4-keto-D-glucose 3-N,N-dimethyltransferase
R11046  dTDP-3-N,N-dimethylamino-2,3,6-trideoxy-4-keto-D-glucose 5-epimerase
R11047   
R11051  dTDP-4-oxo-2,6-dideoxy-D-allose:NADP+ 3-oxidoreductase
R11464   
R11465   
R11466   
R11467   
R11468  dTDP-4-amino-4,6-dideoxy-D-glucose:reduced-ferredoxin:oxygen oxidoreductase
R11469  S-adenosyl-L-methionine:dTDP-L-rhamnose 3'-O-methyltransferase
R11470   
R11471  dTDP-glucose:NAD+ 6-oxidoreductase
R11472  dTDP-D-glucuronate:NAD+ oxidoreductase (decarboxylating)
R11473  dTDP-4-oxo-alpha-D-xylose hydro-lyase (dTDP-4-oxo-2-deoxy-alpha-D-pentos-2-ene-forming)
R11474  dTDP-4-oxo-2-deoxy-beta-L-xylose:NADP+ oxidoreductase
R11475  dTDP-4-amino-2,4-dideoxy-beta-L-xylose:2-oxoglutarate aminotransferase
R11476  S-adenosyl-L-methionine:dTDP-4-amino-2,4-dideoxy-beta-L-xylose N-methyltransferase
Compound
C00103  D-Glucose 1-phosphate
C00688  dTDP-4-dehydro-beta-L-rhamnose
C00842  dTDP-glucose
C03187  dTDP-6-deoxy-beta-L-talose
C03319  dTDP-L-rhamnose
C04268  dTDP-4-amino-4,6-dideoxy-D-glucose
C06017  dTDP-D-glucuronate
C06620  dTDP-3,4-dioxo-2,6-dideoxy-D-glucose
C07277  dTDP-D-fucose
C11447  dTDP-4-dimethylamino-4,6-dideoxy-5-C-methyl-D-allose
C11460  dTDP-4-oxo-5-C-methyl-L-rhamnose
C11461  dTDP-4-amino-4,6-dideoxy-5-C-methyl-D-allose
C11907  dTDP-4-oxo-6-deoxy-D-glucose
C11908  3,6-Dideoxy-3-oxo-dTDP-D-glucose
C11909  dTDP-3-oxo-4,6-dideoxy-D-glucose
C11910  dTDP-3-amino-3,4,6-trideoxy-D-glucose
C11911  dTDP-D-desosamine
C11912  dTDP-6-deoxy-D-allose
C11915  dTDP-3-methyl-4-oxo-2,6-dideoxy-L-allose
C11916  dTDP-L-mycarose
C11918  Maltol
C11919  dTDP-L-megosamine
C11920  dTDP-L-olivose
C11921  dTDP-L-oleandrose
C11922  dTDP-4-oxo-2,6-dideoxy-D-glucose
C11925  dTDP-3-amino-3,6-dideoxy-D-glucose
C11926  dTDP-4-oxo-6-deoxy-D-allose
C11927  dTDP-4-oxo-2,6-dideoxy-L-mannose
C11928  dTDP-4-oxo-2,6-dideoxy-D-allose
C11933  dTDP-D-mycaminose
C12318  dTDP-3-amino-2,3,6-trideoxy-4-keto-D-glucose
C12481  dTDP-5-dimethyl-L-lyxose
C18029  dTDP-3-oxo-2,6-dideoxy-D-glucose
C18030  dTDP-2,6-dideoxy-D-kanosamine
C18031  dTDP-D-angolosamine
C18032  dTDP-4-oxo-2,3,6-trideoxy-D-glucose
C18033  dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose
C18034  dTDP-D-forosamine
C18035  dTDP-3-methyl-4-oxo-2,6-dideoxy-D-glucose
C19947  dTDP-3-amino-3,6-dideoxy-alpha-D-galactopyranose
C19948  dTDP-3-dimethylamino-3,6-dideoxy-alpha-D-galactopyranose
C19960  dTDP-3-dehydro-6-deoxy-alpha-D-galactopyranose
C20156  dTDP-3-acetamido-3,6-dideoxy-alpha-D-galactopyranose
C20682  dTDP-alpha-D-fucofuranose
C21071  dTDP-3-O-methyl-4-oxo-2,6-dideoxy-L-mannose
C21073  dTDP-3-N,N-dimethylamino-2,3,6-trideoxy-4-keto-D-glucose
C21074  dTDP-3-N,N-dimethylamino-4-oxo-2,3,6-trideoxy-L-allose
C21348  dTDP-4-hydroxyamino-4,6-dideoxy-alpha-D-glucose
C21349  dTDP-4-deoxy-4-thio-alpha-D-digitoxose
C21350  dTDP-3-O-methyl-beta-L-rhamnose
C21351  dTDP-4-oxo-alpha-D-xylose
C21352  dTDP-4-oxo-2-deoxy-alpha-D-pentos-2-ene
C21353  dTDP-4-oxo-2-deoxy-beta-L-xylose
C21354  dTDP-4-amino-2,4-dideoxy-beta-L-xylose
C21355  dTDP-4-methylamino-2,4-dideoxy-beta-L-xylose
C21356  dTDP-4-ethylamino-3-O-methyl-2,4-dideoxy-L-threo-pentopyranose
C21362  dTDP-3-methyl-4-oxo-alpha-D-ribopyranose
C21363  dTDP-madurosamine
Reference
  Authors
Rawlings BJ.
  Title
Type I polyketide biosynthesis in bacteria (Part A--erythromycin biosynthesis).
  Journal
Nat Prod Rep 18:190-227 (2001)
DOI:10.1039/b009329g
Reference
  Authors
Rawlings BJ.
  Title
Type I polyketide biosynthesis in bacteria (part B).
  Journal
Nat Prod Rep 18:231-81 (2001)
DOI:10.1039/B100191O
Reference
  Authors
Wohlert S, Lomovskaya N, Kulowski K, Fonstein L, Occi JL, Gewain KM, MacNeil DJ, Hutchinson CR
  Title
Insights about the biosynthesis of the avermectin deoxysugar L-oleandrose through heterologous expression of Streptomyces avermitilis deoxysugar genes in Streptomyces lividans.
  Journal
Chem Biol 8:681-700 (2001)
DOI:10.1016/S1074-5521(01)00043-6
Reference
  Authors
Bate N, Butler AR, Smith IP, Cundliffe E
  Title
The mycarose-biosynthetic genes of Streptomyces fradiae, producer of tylosin.
  Journal
Microbiology 146 ( Pt 1):139-46 (2000)
DOI:10.1099/00221287-146-1-139
Reference
  Authors
Amann S, Drager G, Rupprath C, Kirschning A, Elling L
  Title
(Chemo)enzymatic synthesis of dTDP-activated 2,6-dideoxysugars as building blocks of polyketide antibiotics.
  Journal
Carbohydr Res 335:23-32 (2001)
DOI:10.1016/S0008-6215(01)00195-1
Reference
  Authors
Thibodeaux CJ, Melancon CE, Liu HW
  Title
Unusual sugar biosynthesis and natural product glycodiversification.
  Journal
Nature 446:1008-16 (2007)
DOI:10.1038/nature05814
Reference
  Authors
Volchegursky Y, Hu Z, Katz L, McDaniel R
  Title
Biosynthesis of the anti-parasitic agent megalomicin: transformation of erythromycin to megalomicin in Saccharopolyspora erythraea.
  Journal
Mol Microbiol 37:752-62 (2000)
DOI:10.1046/j.1365-2958.2000.02059.x
Reference
  Authors
Mironov VA, Sergienko OV, Nastasiak IN, Danilenko VN.
  Title
Biogenesis and regulation of biosynthesis of erythromycins in Saccharopolyspora.
  Journal
Appl Biochem Microbiol 40:531-541 (2004)
DOI:10.1023/B:ABIM.0000046985.66328.7a
Reference
  Authors
Tello M, Jakimowicz P, Errey JC, Freel Meyers CL, Walsh CT, Buttner MJ, Lawson DM, Field RA
  Title
Characterisation of Streptomyces spheroides NovW and revision of its functional assignment to a dTDP-6-deoxy-D-xylo-4-hexulose 3-epimerase.
  Journal
Chem Commun (Camb) 1079-81 (2006)
DOI:10.1039/b515763c
Reference
  Authors
Takahashi H, Liu YN, Chen H, Liu HW
  Title
Biosynthesis of TDP-l-mycarose: the specificity of a single enzyme governs the outcome of the pathway.
  Journal
J Am Chem Soc 127:9340-1 (2005)
DOI:10.1021/ja051409x
Reference
  Authors
Aguirrezabalaga I, Olano C, Allende N, Rodriguez L, Brana AF, Mendez C, Salas JA
  Title
Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus.
  Journal
Antimicrob Agents Chemother 44:1266-75 (2000)
DOI:10.1128/AAC.44.5.1266-1275.2000
Reference
  Authors
Rodriguez L, Rodriguez D, Olano C, Brana AF, Mendez C, Salas JA
  Title
Functional analysis of OleY L-oleandrosyl 3-O-methyltransferase of the oleandomycin biosynthetic pathway in Streptomyces antibioticus.
  Journal
J Bacteriol 183:5358-63 (2001)
DOI:10.1128/JB.183.18.5358-5363.2001
Reference
  Authors
Useglio M, Peiru S, Rodriguez E, Labadie GR, Carney JR, Gramajo H
  Title
TDP-L-megosamine biosynthesis pathway elucidation and megalomicin a production in Escherichia coli.
  Journal
Appl Environ Microbiol 76:3869-77 (2010)
DOI:10.1128/AEM.03083-09
Reference
  Authors
Liu W, Christenson SD, Standage S, Shen B
  Title
Biosynthesis of the enediyne antitumor antibiotic C-1027.
  Journal
Science 297:1170-3 (2002)
DOI:10.1126/science.1072110
Reference
  Authors
Van Lanen SG, Oh TJ, Liu W, Wendt-Pienkowski E, Shen B
  Title
Characterization of the maduropeptin biosynthetic gene cluster from Actinomadura madurae ATCC 39144 supporting a unifying paradigm for enediyne biosynthesis.
  Journal
J Am Chem Soc 129:13082-94 (2007)
DOI:10.1021/ja073275o
Reference
  Authors
Gao Q, Zhang C, Blanchard S, Thorson JS
  Title
Deciphering indolocarbazole and enediyne aminodideoxypentose biosynthesis through comparative genomics: insights from the AT2433 biosynthetic locus.
  Journal
Chem Biol 13:733-43 (2006)
DOI:10.1016/j.chembiol.2006.05.009
Reference
  Authors
Simkhada D, Oh TJ, Kim EM, Yoo JC, Sohng JK
  Title
Cloning and characterization of CalS7 from Micromonospora echinospora sp. calichensis as a glucose-1-phosphate nucleotidyltransferase.
  Journal
Biotechnol Lett 31:147-53 (2009)
DOI:10.1007/s10529-008-9844-9
Reference
  Authors
Singh S, Peltier-Pain P, Tonelli M, Thorson JS
  Title
A general NMR-based strategy for the in situ characterization of sugar-nucleotide-dependent biosynthetic pathways.
  Journal
Org Lett 16:3220-3 (2014)
DOI:10.1021/ol501241a
Reference
  Authors
Singh S, Chang A, Helmich KE, Bingman CA, Wrobel RL, Beebe ET, Makino S, Aceti DJ, Dyer K, Hura GL, Sunkara M, Morris AJ, Phillips GN Jr, Thorson JS
  Title
Structural and functional characterization of CalS11, a TDP-rhamnose 3'-O-methyltransferase involved in calicheamicin biosynthesis.
  Journal
ACS Chem Biol 8:1632-9 (2013)
DOI:10.1021/cb400068k
Reference
  Authors
Liang ZX
  Title
Complexity and simplicity in the biosynthesis of enediyne natural products.
  Journal
Nat Prod Rep 27:499-528 (2010)
DOI:10.1039/b908165h
Reference
  Authors
Singh S, Michalska K, Bigelow L, Endres M, Kharel MK, Babnigg G, Yennamalli RM, Bingman CA, Joachimiak A, Thorson JS, Phillips GN Jr
  Title
Structural Characterization of CalS8, a TDP-alpha-D-Glucose Dehydrogenase Involved in Calicheamicin Aminodideoxypentose Biosynthesis.
  Journal
J Biol Chem 290:26249-58 (2015)
DOI:10.1074/jbc.M115.673459
Reference
  Authors
Peltier-Pain P, Singh S, Thorson JS
  Title
Characterization of Early Enzymes Involved in TDP-Aminodideoxypentose Biosynthesis en Route to Indolocarbazole AT2433.
  Journal
Chembiochem 16:2141-6 (2015)
DOI:10.1002/cbic.201500365
Reference
  Authors
Singh S, Kim Y, Wang F, Bigelow L, Endres M, Kharel MK, Babnigg G, Bingman CA, Joachimiak A, Thorson JS, Phillips GN Jr
  Title
Structural characterization of AtmS13, a putative sugar aminotransferase involved in indolocarbazole AT2433 aminopentose biosynthesis.
  Journal
Proteins 83:1547-54 (2015)
DOI:10.1002/prot.24844
Related
pathway
rn00401  Novobiocin biosynthesis
rn00404  Staurosporine biosynthesis
rn00520  Amino sugar and nucleotide sugar metabolism
rn00521  Streptomycin biosynthesis
rn00522  Biosynthesis of 12-, 14- and 16-membered macrolides
rn01059  Biosynthesis of enediyne antibiotics
KO pathway
ko00523   

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