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Entry
map00522                    Pathway                                

Name
Biosynthesis of 12-, 14- and 16-membered macrolides
Class
Metabolism; Metabolism of terpenoids and polyketides
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Biosynthesis of 12-, 14- and 16-membered macrolides
map00522

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Reference
  Authors
Hertweck C
  Title
The biosynthetic logic of polyketide diversity.
  Journal
Angew Chem Int Ed Engl 48:4688-716 (2009)
Reference
  Authors
Long PF, Wilkinson CJ, Bisang CP, Cortes J, Dunster N, Oliynyk M, McCormick E, McArthur H, Mendez C, Salas JA, Staunton J, Leadlay PF
  Title
Engineering specificity of starter unit selection by the erythromycin-producing polyketide synthase.
  Journal
Mol Microbiol 43:1215-25 (2002)
Reference
  Authors
Bisang C, Long PF, Cortes J, Westcott J, Crosby J, Matharu AL, Cox RJ, Simpson TJ, Staunton J, Leadlay PF
  Title
A chain initiation factor common to both modular and aromatic polyketide synthases.
  Journal
Nature 401:502-5 (1999)
Reference
  Authors
Katz L
  Title
The DEBS paradigm for type I modular polyketide synthases and beyond.
  Journal
Methods Enzymol 459:113-42 (2009)
Reference
  Authors
Kittendorf JD, Beck BJ, Buchholz TJ, Seufert W, Sherman DH
  Title
Interrogating the molecular basis for multiple macrolactone ring formation by the pikromycin polyketide synthase.
  Journal
Chem Biol 14:944-54 (2007)
Reference
  Authors
Beck BJ, Yoon YJ, Reynolds KA, Sherman DH
  Title
The hidden steps of domain skipping: macrolactone ring size determination in the  pikromycin modular polyketide synthase.
  Journal
Chem Biol 9:575-83 (2002)
Reference
  Authors
Chen S, Roberts JB, Xue Y, Sherman DH, Reynolds KA
  Title
The Streptomyces venezuelae pikAV gene contains a transcription unit essential for expression of enzymes involved in glycosylation of narbonolide and 10-deoxymethynolide.
  Journal
Gene 263:255-64 (2001)
Reference
  Authors
Kim BS, Cropp TA, Beck BJ, Sherman DH, Reynolds KA
  Title
Biochemical evidence for an editing role of thioesterase II in the biosynthesis of the polyketide pikromycin.
  Journal
J Biol Chem 277:48028-34 (2002)
Reference
  Authors
Ikeda H, Omura S
  Title
Avermectin Biosynthesis.
  Journal
Chem Rev 97:2591-2610 (1997)
Reference
  Authors
Ikeda H, Nonomiya T, Omura S
  Title
Organization of biosynthetic gene cluster for avermectin in Streptomyces avermitilis: analysis of enzymatic domains in four polyketide synthases.
  Journal
J Ind Microbiol Biotechnol 27:170-6 (2001)
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)
Reference
  Authors
Peiru S, Menzella HG, Rodriguez E, Carney J, Gramajo H
  Title
Production of the potent antibacterial polyketide erythromycin C in Escherichia coli.
  Journal
Appl Environ Microbiol 71:2539-47 (2005)
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)
Reference
  Authors
Tsai SC, Miercke LJ, Krucinski J, Gokhale R, Chen JC, Foster PG, Cane DE, Khosla C, Stroud RM
  Title
Crystal structure of the macrocycle-forming thioesterase domain of the erythromycin polyketide synthase: versatility from a unique substrate channel.
  Journal
Proc Natl Acad Sci U S A 98:14808-13 (2001)
Reference
  Authors
Savino C, Montemiglio LC, Sciara G, Miele AE, Kendrew SG, Jemth P, Gianni S, Vallone B
  Title
Investigating the structural plasticity of a cytochrome P450: three-dimensional structures of P450 EryK and binding to its physiological substrate.
  Journal
J Biol Chem 284:29170-9 (2009)
Reference
PMID:8300527
  Authors
Hsieh YJ, Kolattukudy PE.
  Title
Inhibition of erythromycin synthesis by disruption of malonyl-coenzyme A decarboxylase gene eryM in Saccharopolyspora erythraea.
  Journal
J Bacteriol 176:714-24 (1994)
Reference
PMID:8830278
  Authors
Donadio S, Staver MJ, Katz L.
  Title
Erythromycin production in Saccharopolyspora erythraea does not require a functional propionyl-CoA carboxylase.
  Journal
Mol Microbiol 19:977-84 (1996)
Reference
PMID:9353926
  Authors
Summers RG, Donadio S, Staver MJ, Wendt-Pienkowski E, Hutchinson CR, Katz L.
  Title
Sequencing and mutagenesis of genes from the erythromycin biosynthetic gene cluster of Saccharopolyspora erythraea that are involved in L-mycarose and D-desosamine production.
  Journal
Microbiology 143:3251-62 (1997)
Reference
  Authors
Rawlings BJ.
  Title
Type I polyketide biosynthesis in bacteria (part B).
  Journal
Nat Prod Rep 18:231-81 (2001)
Reference
  Authors
Rawlings BJ.
  Title
Type I polyketide biosynthesis in bacteria (Part A--erythromycin biosynthesis).
  Journal
Nat Prod Rep 18:190-227 (2001)
Reference
  Authors
Borisova SA, Liu HW
  Title
Characterization of glycosyltransferase DesVII and its auxiliary partner protein  DesVIII in the methymycin/picromycin biosynthetic pathway.
  Journal
Biochemistry 49:8071-84 (2010)
Reference
  Authors
Hong JS, Park SJ, Parajuli N, Park SR, Koh HS, Jung WS, Choi CY, Yoon YJ
  Title
Functional analysis of desVIII homologues involved in glycosylation of macrolide  antibiotics by interspecies complementation.
  Journal
Gene 386:123-30 (2007)
Reference
  Authors
Rodriguez E, Peiru S, Carney JR, Gramajo H
  Title
In vivo characterization of the dTDP-D-desosamine pathway of the megalomicin gene cluster from Micromonospora megalomicea.
  Journal
Microbiology 152:667-73 (2006)
Reference
  Authors
Moncrieffe MC, Fernandez MJ, Spiteller D, Matsumura H, Gay NJ, Luisi BF, Leadlay PF
  Title
Structure of the glycosyltransferase EryCIII in complex with its activating P450  homologue EryCII.
  Journal
J Mol Biol 415:92-101 (2012)
Reference
  Authors
Yuan Y, Chung HS, Leimkuhler C, Walsh CT, Kahne D, Walker S
  Title
In vitro reconstitution of EryCIII activity for the preparation of unnatural macrolides.
  Journal
J Am Chem Soc 127:14128-9 (2005)
Reference
  Authors
Sherman DH, Li S, Yermalitskaya LV, Kim Y, Smith JA, Waterman MR, Podust LM
  Title
The structural basis for substrate anchoring, active site selectivity, and product formation by P450 PikC from Streptomyces venezuelae.
  Journal
J Biol Chem 281:26289-97 (2006)
Reference
  Authors
Li S, Ouellet H, Sherman DH, Podust LM
  Title
Analysis of transient and catalytic desosamine-binding pockets in cytochrome P-450 PikC from Streptomyces venezuelae.
  Journal
J Biol Chem 284:5723-30 (2009)
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