Literature DB >> 22688446

The structural biology of enzymes involved in natural product glycosylation.

Shanteri Singh1, George N Phillips, Jon S Thorson.   

Abstract

The glycosylation of microbial natural products often dramatically influences the biological and/or pharmacological activities of the parental metabolite. Over the past decade, crystal structures of several enzymes involved in the biosynthesis and attachment of novel sugars found appended to natural products have emerged. In many cases, these studies have paved the way to a better understanding of the corresponding enzyme mechanism of action and have served as a starting point for engineering variant enzymes to facilitate to production of differentially-glycosylated natural products. This review specifically summarizes the structural studies of bacterial enzymes involved in biosynthesis of novel sugar nucleotides.

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Year:  2012        PMID: 22688446      PMCID: PMC3627186          DOI: 10.1039/c2np20039b

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  226 in total

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Authors:  Tanja M Wrodnigg; Friedrich K Fitz Sprenger
Journal:  Mini Rev Med Chem       Date:  2004-05       Impact factor: 3.862

2.  Crystal structure of potato tuber ADP-glucose pyrophosphorylase.

Authors:  Xiangshu Jin; Miguel A Ballicora; Jack Preiss; James H Geiger
Journal:  EMBO J       Date:  2005-02-03       Impact factor: 11.598

3.  Dramatic differences in the binding of UDP-galactose and UDP-glucose to UDP-galactose 4-epimerase from Escherichia coli.

Authors:  J B Thoden; H M Holden
Journal:  Biochemistry       Date:  1998-08-18       Impact factor: 3.162

4.  Expanding pyrimidine diphosphosugar libraries via structure-based nucleotidylyltransferase engineering.

Authors:  William A Barton; John B Biggins; Jiqing Jiang; Jon S Thorson; Dimitar B Nikolov
Journal:  Proc Natl Acad Sci U S A       Date:  2002-10-08       Impact factor: 11.205

5.  Structural and functional characterization of PseC, an aminotransferase involved in the biosynthesis of pseudaminic acid, an essential flagellar modification in Helicobacter pylori.

Authors:  Ian C Schoenhofen; Vladimir V Lunin; Jean-Philippe Julien; Yunge Li; Eunice Ajamian; Allan Matte; Miroslaw Cygler; Jean-Robert Brisson; Annie Aubry; Susan M Logan; Smita Bhatia; Warren W Wakarchuk; N Martin Young
Journal:  J Biol Chem       Date:  2006-01-18       Impact factor: 5.157

6.  Chemoenzymatic synthesis, inhibition studies, and X-ray crystallographic analysis of the phosphono analog of UDP-Galp as an inhibitor and mechanistic probe for UDP-galactopyranose mutase.

Authors:  Sarathy Karunan Partha; Ali Sadeghi-Khomami; Kathryn Slowski; Toshihisa Kotake; Neil R Thomas; David L Jakeman; David A R Sanders
Journal:  J Mol Biol       Date:  2010-09-17       Impact factor: 5.469

7.  The structure of glucose-fructose oxidoreductase from Zymomonas mobilis: an osmoprotective periplasmic enzyme containing non-dissociable NADP.

Authors:  R L Kingston; R K Scopes; E N Baker
Journal:  Structure       Date:  1996-12-15       Impact factor: 5.006

8.  Dehydration is catalyzed by glutamate-136 and aspartic acid-135 active site residues in Escherichia coli dTDP-glucose 4,6-dehydratase.

Authors:  J W Gross; A D Hegeman; B Gerratana; P A Frey
Journal:  Biochemistry       Date:  2001-10-23       Impact factor: 3.162

Review 9.  Increasing carbohydrate diversity via amine oxidation: aminosugar, hydroxyaminosugar, nitrososugar, and nitrosugar biosynthesis in bacteria.

Authors:  Shannon C Timmons; Jon S Thorson
Journal:  Curr Opin Chem Biol       Date:  2008-04-18       Impact factor: 8.822

Review 10.  Engineering the glycosylation of natural products in actinomycetes.

Authors:  José A Salas; Carmen Méndez
Journal:  Trends Microbiol       Date:  2007-04-06       Impact factor: 17.079

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  33 in total

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Journal:  Chembiochem       Date:  2014-11-03       Impact factor: 3.164

Review 2.  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

3.  Structural characterization of O- and C-glycosylating variants of the landomycin glycosyltransferase LanGT2.

Authors:  Heng Keat Tam; Johannes Härle; Stefan Gerhardt; Jürgen Rohr; Guojun Wang; Jon S Thorson; Aurélien Bigot; Monika Lutterbeck; Wolfgang Seiche; Bernhard Breit; Andreas Bechthold; Oliver Einsle
Journal:  Angew Chem Int Ed Engl       Date:  2015-01-07       Impact factor: 15.336

4.  Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine.

Authors:  Guillaume Pelletier; Aaron Zwicker; C Liana Allen; Alanna Schepartz; Scott J Miller
Journal:  J Am Chem Soc       Date:  2016-03-01       Impact factor: 15.419

5.  Structural Basis for the Stereochemical Control of Amine Installation in Nucleotide Sugar Aminotransferases.

Authors:  Fengbin Wang; Shanteri Singh; Weijun Xu; Kate E Helmich; Mitchell D Miller; Hongnan Cao; Craig A Bingman; Jon S Thorson; George N Phillips
Journal:  ACS Chem Biol       Date:  2015-06-23       Impact factor: 5.100

6.  Crystal Structure of the N-Acetylmuramic Acid α-1-Phosphate (MurNAc-α1-P) Uridylyltransferase MurU, a Minimal Sugar Nucleotidyltransferase and Potential Drug Target Enzyme in Gram-negative Pathogens.

Authors:  Michaela Renner-Schneck; Isabel Hinderberger; Jonathan Gisin; Thomas Exner; Christoph Mayer; Thilo Stehle
Journal:  J Biol Chem       Date:  2015-03-12       Impact factor: 5.157

7.  Characterization of Early Enzymes Involved in TDP-Aminodideoxypentose Biosynthesis en Route to Indolocarbazole AT2433.

Authors:  Pauline Peltier-Pain; Shanteri Singh; Jon S Thorson
Journal:  Chembiochem       Date:  2015-09-18       Impact factor: 3.164

8.  Broadening the scope of glycosyltransferase-catalyzed sugar nucleotide synthesis.

Authors:  Richard W Gantt; Pauline Peltier-Pain; Shanteri Singh; Maoquan Zhou; Jon S Thorson
Journal:  Proc Natl Acad Sci U S A       Date:  2013-04-22       Impact factor: 11.205

9.  Glycogenomics as a mass spectrometry-guided genome-mining method for microbial glycosylated molecules.

Authors:  Roland D Kersten; Nadine Ziemert; David J Gonzalez; Brendan M Duggan; Victor Nizet; Pieter C Dorrestein; Bradley S Moore
Journal:  Proc Natl Acad Sci U S A       Date:  2013-11-04       Impact factor: 11.205

10.  Synthesis and antibacterial activity of doxycycline neoglycosides.

Authors:  Jianjun Zhang; Larissa V Ponomareva; Karen Marchillo; Maoquan Zhou; David R Andes; Jon S Thorson
Journal:  J Nat Prod       Date:  2013-08-29       Impact factor: 4.050

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