Literature DB >> 12444703

Digitoxosyltetracenomycin C and glucosyltetracenomycin C, two novel elloramycin analogues obtained by exploring the sugar donor substrate specificity of glycosyltransferase ElmGT.

Carsten Fischer1, Leticia Rodríguez, Eugenio P Patallo, Fredilyn Lipata, Alfredo F Braña, Carmen Méndez, Jose A Salas, Jürgen Rohr.   

Abstract

Our explorations of glycosyltransferase ElmGT from Streptomyces olivaceus Tü 2353, which shows an interesting flexibility regarding its sugar donor substrate, were extended toward various previously unexplored sugar co-substrates. The studies revealed that ElmGT, which normally transfers L-rhamnose to 8-demethyltetracenomycin C as a crucial biosynthetic step in elloramycin biosynthesis, is also able to process an activated non-deoxygenated sugar, NDP-D-glucose, as well as NDP-L-digitoxose, which is the first example of an NDP-L-sugar co-substrate of ElmGT possessing an axial 3-OH group. The structures of the resulting novel elloramycin analogues of these experiments, 8-demethyl-8-L-digitoxosyltetracenomycin C (4) and 8-demethyl-8-D-glucosyltetracenomycin C (7), were elucidated mainly by (1)H and (13)C NMR spectroscopy and by mass spectrometry.

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Year:  2002        PMID: 12444703     DOI: 10.1021/np020112z

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  14 in total

1.  Enzymatic basis of "hybridity" in thiomarinol biosynthesis.

Authors:  Zachary D Dunn; Walter J Wever; Nicoleta J Economou; Albert A Bowers; Bo Li
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-26       Impact factor: 15.336

2.  Development of a Streptomyces venezuelae-based combinatorial biosynthetic system for the production of glycosylated derivatives of doxorubicin and its biosynthetic intermediates.

Authors:  Ah Reum Han; Je Won Park; Mi Kyeong Lee; Yeon Hee Ban; Young Ji Yoo; Eun Ji Kim; Eunji Kim; Byung-Gee Kim; Jae Kyung Sohng; Yeo Joon Yoon
Journal:  Appl Environ Microbiol       Date:  2011-05-20       Impact factor: 4.792

Review 3.  A comprehensive review of glycosylated bacterial natural products.

Authors:  Sherif I Elshahawi; Khaled A Shaaban; Madan K Kharel; Jon S Thorson
Journal:  Chem Soc Rev       Date:  2015-11-07       Impact factor: 54.564

4.  Ketoolivosyl-tetracenomycin C: a new ketosugar bearing tetracenomycin reveals new insight into the substrate flexibility of glycosyltransferase ElmGT.

Authors:  S Eric Nybo; Khaled A Shabaan; Madan K Kharel; Happy Sutardjo; José A Salas; Carmen Méndez; Jürgen Rohr
Journal:  Bioorg Med Chem Lett       Date:  2012-02-03       Impact factor: 2.823

5.  Combinatorial biosynthesis of antitumor deoxysugar pathways in Streptomyces griseus: Reconstitution of "unnatural natural gene clusters" for the biosynthesis of four 2,6-D-dideoxyhexoses.

Authors:  María Pérez; Felipe Lombó; Irfan Baig; Alfredo F Braña; Jürgen Rohr; José A Salas; Carmen Méndez
Journal:  Appl Environ Microbiol       Date:  2006-10       Impact factor: 4.792

6.  Deciphering the late steps in the biosynthesis of the anti-tumour indolocarbazole staurosporine: sugar donor substrate flexibility of the StaG glycosyltransferase.

Authors:  Aaroa P Salas; Lili Zhu; César Sánchez; Alfredo F Braña; Jürgen Rohr; Carmen Méndez; José A Salas
Journal:  Mol Microbiol       Date:  2005-10       Impact factor: 3.501

7.  Modulation of deoxysugar transfer by the elloramycin glycosyltransferase ElmGT through site-directed mutagenesis.

Authors:  Angelina Ramos; Carlos Olano; Alfredo F Braña; Carmen Méndez; José A Salas
Journal:  J Bacteriol       Date:  2009-02-20       Impact factor: 3.490

8.  Pathway Engineering of Anthracyclines: Blazing Trails in Natural Product Glycodiversification.

Authors:  Katelyn V Brown; Benjamin Nji Wandi; Mikko Metsä-Ketelä; S Eric Nybo
Journal:  J Org Chem       Date:  2020-09-22       Impact factor: 4.354

Review 9.  Natural-product sugar biosynthesis and enzymatic glycodiversification.

Authors:  Christopher J Thibodeaux; Charles E Melançon; Hung-wen Liu
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 10.  Engineering biosynthetic pathways to generate antitumor indolocarbazole derivatives.

Authors:  César Sánchez; Carmen Méndez; José A Salas
Journal:  J Ind Microbiol Biotechnol       Date:  2006-02-21       Impact factor: 3.346

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