The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster.

@article{Hoffmeister2000TheNC,
  title={The NDP-sugar co-substrate concentration and the enzyme expression level influence the substrate specificity of glycosyltransferases: cloning and characterization of deoxysugar biosynthetic genes of the urdamycin biosynthetic gene cluster.},
  author={Dirk Hoffmeister and Koji Ichinose and Silvie Domann and Belinda Faust and A. Trefzer and Gerald Dr{\"a}ger and Andreas Kirschning and Carsten Fischer and Eva K{\"u}nzel and Daniel W. Bearden and J{\"u}rgen Rohr and Andreas Bechthold},
  journal={Chemistry \& biology},
  year={2000},
  volume={7 11},
  pages={
          821-31
        }
}
BACKGROUND Streptomyces fradiae is the principal producer of urdamycin A. The antibiotic consists of a polyketide-derived aglycone, which is glycosylated with four sugar components, 2x D-olivose (first and last sugar of a C-glycosidically bound trisaccharide chain at the 9-position), and 2x L-rhodinose (in the middle of the trisaccharide chain and at the 12b-position). Limited information is available about both the biosynthesis of D-olivose and L-rhodinose and the influence of the… Expand
Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity.
TLDR
It is demonstrated that it is an N-terminal section that determines specificity for the nucleotide sugar and also the acceptor substrate of these two urdamycin GTs, directing the way towards engineering this class of streptomycete enzymes for antibiotic derivatization applications. Expand
Engineering biosynthetic pathways for deoxysugars: branched-chain sugar pathways and derivatives from the antitumor tetracenomycin.
TLDR
Formation of two compounds represents examples of the sugar cosubstrate flexibility of the ElmGT glycosyltransferase, and provided insights into the substrate flexibility of deoxysugar biosynthesis enzymes as the C-methyltransferases EryBIII and MtmC, the epimerases OleL and EryBVII, and the 4-ketoreductases ERYV and OleU. Expand
Elucidation of the function of two glycosyltransferase genes (lanGT1 and lanGT4) involved in landomycin biosynthesis and generation of new oligosaccharide antibiotics.
TLDR
The high-yielding production of novel oligosaccharide antibiotics using glycosyltransferase gene cassettes generated in a very convenient way proves that glycosYLtransferases can be flexible towards the alcohol substrate. Expand
Engineering deoxysugar biosynthetic pathways from antibiotic-producing microorganisms. A tool to produce novel glycosylated bioactive compounds.
A plasmid (pLN2) was generated in which genes involved in the biosynthesis of L-oleandrose in the oleandomycin producer Streptomyces antibioticus ATCC11891 were cloned. pLN2 was used to direct theExpand
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TLDR
The biosynthetic gene cluster for the dienoyltetramic acid streptolydigin was identified and characterized from the producer organism Streptomyces lydicus NRRL2433, with a certain degree of flexibility of the L-rhodinosyl transferase SlgG for the recognition of 2,3, 6-trideoxyhexoses and 2,6-dideoxy hexoses, both in D- and L- configuration. Expand
Characterisation of the genes involved in the biosynthesis and attachment of the aminodeoxysugar d-forosamine in the auricin gene cluster of Streptomyces aureofaciens CCM3239
TLDR
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Analysis by HPLC and NMR of intermediates accumulated by cultures of the insertionally inactivated Streptomyces venezuelae mutants indicated that jadO, P, Q, S, T, U and V mediate formation of the dideoxysugar moiety of jadomycin B and its attachment to the aglycone. Expand
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TLDR
The biochemical functions of the five enzymes involved in TDP-D-forosamine formation have now been fully elucidated and reveal that SpnO and SpnN functions as a 2,3-dehydrase and a 3-ketoreductase, respectively. Expand
Biosynthesis of the orthosomycin antibiotic avilamycin A: deductions from the molecular analysis of the avi biosynthetic gene cluster of Streptomyces viridochromogenes Tü57 and production of new antibiotics.
TLDR
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Cloning, sequencing and heterologous expression of the medermycin biosynthetic gene cluster of Streptomyces sp. AM-7161: towards comparative analysis of the benzoisochromanequinone gene clusters.
TLDR
Comparison among the three complete BIQ gene clusters revealed some common genes whose deduced functions are unavailable from database searches (the 'unknowns'), which suggests a possible involvement of conventional C-glycosylation in medermycin biosynthesis. Expand
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INACTIVATION OF THE URDGT2 GENE, WHICH ENCODES A GLYCOSYLTRANSFERASE RESPONSIBLE FOR THE C-GLYCOSYLTRANSFER OF ACTIVATED D-OLIVOSE, LEADS TO FORMATION OF THE NOVEL URDAMYCINS I, J, AND K
A targeted search for glycosyltransferase (GT) encoding genes in the gene cluster of the urdamycin A producer Streptomyces fradiae Tu2717 resulted in the discovery of urdGT2, a GT encoding geneExpand
Function of glycosyltransferase genes involved in urdamycin A biosynthesis.
TLDR
Analysis of glycosyltransferase genes of the urdamycin biosynthetic gene cluster led to an unambiguous assignment of each glycosYLtransferase to a certain biosynthesis saccharide attachment step. Expand
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Putative functional assignments of the products of most of the newly discovered ORFs were made, including those of genes involved in the PKS and tailoring Steps in the biosynthesis of the granaticin aglycone, steps in the deoxy sugar pathway, and putative regulatory and export functions. Expand
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It is concluded that glycosylated macrolides exert a pronounced positive effect on polyketide metabolism in S. fradiae. Expand
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TLDR
Rifamycin production in A. mediterranei is governed by a single gene cluster consisting of structural, resistance and export, and regulatory genes that could be modified to produce novel forms of the rifamycins that may be effective against rif amycin-resistant microorganisms. Expand
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TLDR
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Analysis of the gene cluster from Streptomyces avermitilis that governs the biosynthesis of the polyketide anthelmintic avermectin revealed that it contains four large ORFs encoding giantExpand
Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus
TLDR
A model is proposed integrating these and previously reported results for intracellular inactivation, secretion and extracellular reactivation of oleandomycin, with OleI being much more specific for ole fandomycin. Expand
Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin
TLDR
Two genes (mtmD and mtmE) were cloned and sequenced from the mithramycin producer Streptomyces argillaceus and showed that they encode a glucose-1-phosphate:TTP thymidylyl transferase and a TDP-D-glucose 4,6-dehydratase, respectively. Expand
Interspecies complementation in Saccharopolyspora erythraea : elucidation of the function of oleP1, oleG1 and oleG2 from the oleandomycin biosynthetic gene cluster of Streptomyces antibioticus and generation of new erythromycin derivatives
TLDR
Interspecies complementation has been carried out, using two mutant strains of Saccharopolyspora erythraea to identify which of these two glycosyltransferases encodes the desosaminyltransferase and which the oleandrosyltransferase, and to demonstrate that the function of OleP1 is identical to that of EryCII in the biosynthesis of dTDP‐d‐desosamine. Expand
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