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Literature DB >> 21960454

Investigating Mithramycin deoxysugar biosynthesis: enzymatic total synthesis of TDP-D-olivose.

Guojun Wang¹, Madan K Kharel, Pallab Pahari, Jürgen Rohr.

Abstract

Mix'n'match: Enzymatic total synthesis of TDP-D-olivose was achieved, starting from TDP-4-keto-6-deoxy-D-glucose, by combining three pathway enzymes with one cofactor-regenerating enzyme. The results also revealed that MtmC is a bifunctional enzyme that can perform a 4-ketoreduction necessary for D-olivose biosynthesis besides the previously found C-methyltransfer for D-mycarose biosynthesis.

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Year: 2011 PMID： 21960454 PMCID： PMC3412565 DOI： 10.1002/cbic.201100540

Source DB: PubMed Journal: Chembiochem ISSN： 1439-4227 Impact factor: 3.164

33 in total

1. Insights into the Branched-Chain Formation of Mycarose: Methylation Catalyzed by an (S)-Adenosylmethionine-Dependent Methyltransferase We are grateful to Dr. Eugene Seno and the Lilly Research Laboratories for their generous gift of the plasmid pHJL311 and to the National Institutes of Health for grants (GM 35 906 and 54 346). H.-w.L. also thanks the National Institute of General Medical Sciences for a MERIT Award. T.M.H. was a trainee of the National Institute of General Medical Sciences (Biotechnology Training Grant: 2 T32 GM08347).

Authors: Huawei Chen; Zongbao Zhao; Tina M. Hallis; Zhihong Guo
Journal: Angew Chem Int Ed Engl Date: 2001-02-02 Impact factor: 15.336

2. 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.

Authors: D Hoffmeister; K Ichinose; S Domann; B Faust; A Trefzer; G Dräger; A Kirschning; C Fischer; E Künzel; D Bearden; J Rohr; A Bechthold
Journal: Chem Biol Date: 2000-11

3. Characterization of Streptomyces nogalater genes encoding enzymes involved in glycosylation steps in nogalamycin biosynthesis.

Authors: S Torkkell; K Ylihonko; J Hakala; M Skurnik; P Mäntsälä
Journal: Mol Gen Genet Date: 1997-09

4. Elucidation of the glycosylation sequence of mithramycin biosynthesis: isolation of 3A-deolivosylpremithramycin B and its conversion to premithramycin B by glycosyltransferase MtmGII.

Authors: Mohammad Nur-e-Alam; Carmen Méndez; José A Salas; Jürgen Rohr
Journal: Chembiochem Date: 2005-04 Impact factor: 3.164

Review 5. The aureolic acid family of antitumor compounds: structure, mode of action, biosynthesis, and novel derivatives.

Authors: Felipe Lombó; Nuria Menéndez; José A Salas; Carmen Méndez
Journal: Appl Microbiol Biotechnol Date: 2006-09-30 Impact factor: 4.813

6. Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus.

Authors: I Aguirrezabalaga; C Olano; N Allende; L Rodriguez; A F Braña; C Méndez; J A Salas
Journal: Antimicrob Agents Chemother Date: 2000-05 Impact factor: 5.191

7. The mtmVUC genes of the mithramycin gene cluster in Streptomyces argillaceus are involved in the biosynthesis of the sugar moieties.

Authors: A González; L L Remsing; F Lombó; M J Fernández; L Prado; A F Braña; E Künzel; J Rohr; C Méndez; J A Salas
Journal: Mol Gen Genet Date: 2001-02

8. Cloning and insertional inactivation of Streptomyces argillaceus genes involved in the earliest steps of biosynthesis of the sugar moieties of the antitumor polyketide mithramycin.

Authors: F Lombó; K Siems; A F Braña; C Méndez; K Bindseil; J A Salas
Journal: J Bacteriol Date: 1997-05 Impact factor: 3.490

9. Substrate flexibility of vicenisaminyltransferase VinC involved in the biosynthesis of vicenistatin.

Authors: Atsushi Minami; Tadashi Eguchi
Journal: J Am Chem Soc Date: 2007-03-28 Impact factor: 15.419

10. Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity.

Authors: Dirk Hoffmeister; Barrie Wilkinson; Graham Foster; Philip J Sidebottom; Koji Ichinose; Andreas Bechthold
Journal: Chem Biol Date: 2002-03

8 in total

1. Molecular insight into substrate recognition and catalysis of Baeyer-Villiger monooxygenase MtmOIV, the key frame-modifying enzyme in the biosynthesis of anticancer agent mithramycin.

Authors: Mary A Bosserman; Theresa Downey; Nicholas Noinaj; Susan K Buchanan; Jürgen Rohr
Journal: ACS Chem Biol Date: 2013-09-13 Impact factor: 5.100

2. Arginine-rhamnosylation as new strategy to activate translation elongation factor P.

Authors: Jürgen Lassak; Eva C Keilhauer; Maximilian Fürst; Kristin Wuichet; Julia Gödeke; Agata L Starosta; Jhong-Min Chen; Lotte Søgaard-Andersen; Jürgen Rohr; Daniel N Wilson; Susanne Häussler; Matthias Mann; Kirsten Jung
Journal: Nat Chem Biol Date: 2015-02-16 Impact factor: 15.040

3. Cooperation of two bifunctional enzymes in the biosynthesis and attachment of deoxysugars of the antitumor antibiotic mithramycin.

Authors: Guojun Wang; Pallab Pahari; Madan K Kharel; Jing Chen; Haining Zhu; Steven G Van Lanen; Jürgen Rohr
Journal: Angew Chem Int Ed Engl Date: 2012-09-20 Impact factor: 15.336