KEGG   PATHWAY: sml00523Help
Entry
sml00523                    Pathway                                

Name
Polyketide sugar unit biosynthesis - Stenotrophomonas maltophilia K279a
Class
Metabolism; Metabolism of terpenoids and polyketides
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Pathway map
Polyketide sugar unit biosynthesis
sml00523

All organismsOrtholog table
Module
dTDP-L-rhamnose biosynthesis [PATH:sml00523]
Organism
Stenotrophomonas maltophilia K279a [GN:sml]
Gene
rmlA; putative glucose-1-phosphate thymidylyltransferase [KO:K00973] [EC:2.7.7.24]
rmlB; putative dTDP-glucose 4,6-dehydratase [KO:K01710] [EC:4.2.1.46]
rmlC; putative DTDP-dehydrorhamnose 3,5-epimerase [KO:K01790] [EC:5.1.3.13]
rmlD; putative dTDP-4-dehydrorhamnose reductase [KO:K00067] [EC:1.1.1.133]
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
Applied Biochemistry and Microbiology 40(6): 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
KO pathway
 

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