Literature DB >> 29953217

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Matteo Panza1, Salvatore G Pistorio1, Keith J Stine1, Alexei V Demchenko1.   

Abstract

Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

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Year:  2018        PMID: 29953217      PMCID: PMC6522228          DOI: 10.1021/acs.chemrev.8b00051

Source DB:  PubMed          Journal:  Chem Rev        ISSN: 0009-2665            Impact factor:   60.622


  365 in total

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Journal:  Chemistry       Date:  2002-10-04       Impact factor: 5.236

2.  Stereospecific 1,2-cis-glycosylation: a modified thiocyanate method.

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Journal:  Carbohydr Res       Date:  1992-07-20       Impact factor: 2.104

Review 3.  Advances in Stereoselective 1,2-cis Glycosylation using C-2 Auxiliaries.

Authors:  Rens A Mensink; Thomas J Boltje
Journal:  Chemistry       Date:  2017-10-04       Impact factor: 5.236

Review 4.  Polysaccharide vaccines as probes of antibody repertoires in man.

Authors:  A H Lucas; D C Reason
Journal:  Immunol Rev       Date:  1999-10       Impact factor: 12.988

5.  C6 picoloyl protection: a remote stereodirecting group for 2-deoxy-β-glycoside formation.

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Journal:  Chem Commun (Camb)       Date:  2015-03-28       Impact factor: 6.222

6.  Elevated globotriaosylsphingosine is a hallmark of Fabry disease.

Authors:  Johannes M Aerts; Johanna E Groener; Sijmen Kuiper; Wilma E Donker-Koopman; Anneke Strijland; Roelof Ottenhoff; Cindy van Roomen; Mina Mirzaian; Frits A Wijburg; Gabor E Linthorst; Anouk C Vedder; Saskia M Rombach; Josanne Cox-Brinkman; Pentti Somerharju; Rolf G Boot; Carla E Hollak; Roscoe O Brady; Ben J Poorthuis
Journal:  Proc Natl Acad Sci U S A       Date:  2008-02-19       Impact factor: 11.205

7.  Synthesis of oligosaccharides on soluble high-molecular-weight branched polymers in combination with purification by nanofiltration.

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Journal:  Org Lett       Date:  2003-10-02       Impact factor: 6.005

8.  Role of glycosaminoglycans in cellular communication.

Authors:  Robert J Linhardt; Toshihiko Toida
Journal:  Acc Chem Res       Date:  2004-07       Impact factor: 22.384

9.  Linker influence on the stereochemical outcome of glycosylations utilizing solid support-bound glycosyl phosphates.

Authors:  Diana K Hunt; Peter H Seeberger
Journal:  Org Lett       Date:  2002-08-08       Impact factor: 6.005

10.  Palladium-controlled beta-selective glycosylation in the absence of the C(2)-ester participatory group.

Authors:  Enoch A Mensah; Joseph M Azzarelli; Hien M Nguyen
Journal:  J Org Chem       Date:  2009-02-20       Impact factor: 4.354

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  53 in total

Review 1.  Recent advances in site-selective functionalization of carbohydrates mediated by organocatalysts.

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2.  Picoloyl protecting group in synthesis: focus on a highly chemoselective catalytic removal.

Authors:  Scott A Geringer; Michael P Mannino; Mithila D Bandara; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2020-07-01       Impact factor: 3.876

Review 3.  Expedient Synthesis of Core Disaccharide Building Blocks from Natural Polysaccharides for Heparan Sulfate Oligosaccharide Assembly.

Authors:  Nitin J Pawar; Lei Wang; Takuya Higo; Chandrabali Bhattacharya; Pavan K Kancharla; Fuming Zhang; Kedar Baryal; Chang-Xin Huo; Jian Liu; Robert J Linhardt; Xuefei Huang; Linda C Hsieh-Wilson
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-06       Impact factor: 15.336

Review 4.  Oligosaccharide Synthesis and Translational Innovation.

Authors:  Larissa Krasnova; Chi-Huey Wong
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Review 5.  Synthesis of carbohydrate building blocks via regioselective uniform protection/deprotection strategies.

Authors:  Tinghua Wang; Alexei V Demchenko
Journal:  Org Biomol Chem       Date:  2019-05-02       Impact factor: 3.876

6.  Unraveling the isomeric heterogeneity of glycans: ion mobility separations in structures for lossless ion manipulations.

Authors:  Gabe Nagy; Isaac K Attah; Sandilya V B Garimella; Keqi Tang; Yehia M Ibrahim; Erin S Baker; Richard D Smith
Journal:  Chem Commun (Camb)       Date:  2018-09-28       Impact factor: 6.222

7.  Preparative scale purification of natural glycans by closed-loop recycle HPLC.

Authors:  Yuyang Zhu; Thomas J Bowen; Xuezheng Song
Journal:  Anal Biochem       Date:  2020-04-08       Impact factor: 3.365

8.  Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals.

Authors:  Subbarao Yalamanchili; Tu-Anh V Nguyen; Nicola L B Pohl; Clay S Bennett
Journal:  Org Biomol Chem       Date:  2020-05-06       Impact factor: 3.876

9.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

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Review 10.  Recent progress in chemical synthesis of bacterial surface glycans.

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