Literature DB >> 32785304

The development of a dedicated polymer support for the solid-phase oligosaccharide synthesis.

Matteo Panza1, Dharmendra Neupane, Keith J Stine, Alexei V Demchenko.   

Abstract

Reported herein is the development of a novel polystyrene-based resin that we named PanzaGel. The resin was equipped with diethylene glycol-derived cross-linker with the dedicated application to polymer supported glycan synthesis in mind. After investigating its swelling properties and obtaining encouraging data for its chemical and thermal stability we accessed the amenability of PanzaGel to the HPLC-based platform for the automated synthesis. Comparable glycosylation results to those with traditional supports have been obtained in the synthesis of glycans up to pentasaccharide that was obtained in 30% overall yield. The automated synthesis set-up implemented a common analytical autosampler for delivering all reagents for all steps of the glycan synthesis and cleavage.

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Year:  2020        PMID: 32785304      PMCID: PMC7658588          DOI: 10.1039/d0cc03885g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  16 in total

1.  Asymmetric Diels-Alder Reaction of Methacrolein with Cyclopentadiene Using Polymer-Supported Catalysts: Design of Highly Enantioselective Polymeric Catalysts.

Authors:  Koichi Kamahori; Koichi Ito; Shinichi Itsuno
Journal:  J Org Chem       Date:  1996-11-15       Impact factor: 4.354

2.  Organic polymer supports for synthesis and for reagent and catalyst immobilization.

Authors:  Jinni Lu; Patrick H Toy
Journal:  Chem Rev       Date:  2009-02       Impact factor: 60.622

Review 3.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

Review 4.  Polymeric supports for solid phase synthesis.

Authors:  J W Labadie
Journal:  Curr Opin Chem Biol       Date:  1998-06       Impact factor: 8.822

5.  Synthesis of an Fmoc-threonine bearing core-2 glycan: a building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis.

Authors:  Venkata R Krishnamurthy; Ann Dougherty; Medha Kamat; Xuezheng Song; Richard D Cummings; Elliot L Chaikof
Journal:  Carbohydr Res       Date:  2010-05-12       Impact factor: 2.104

6.  Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis.

Authors:  P H Toy; T S Reger; P Garibay; J C Garno; J A Malikayil; G Liu; K D Janda
Journal:  J Comb Chem       Date:  2001 Jan-Feb

7.  Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans.

Authors:  Salvatore G Pistorio; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2019-05-17       Impact factor: 4.354

8.  HPLC-Assisted Automated Oligosaccharide Synthesis: Implementation of the Autosampler as a Mode of the Reagent Delivery.

Authors:  Salvatore G Pistorio; Swati S Nigudkar; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2016-09-14       Impact factor: 4.354

9.  Chemistry-driven glycoscience.

Authors:  Laura L Kiessling
Journal:  Bioorg Med Chem       Date:  2018-09-22       Impact factor: 3.641

10.  Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker.

Authors:  Mayeul Collot; Steffen Eller; Markus Weishaupt; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2013-01-16       Impact factor: 2.883

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  1 in total

1.  HPLC-Based Automated Synthesis of Glycans in Solution.

Authors:  Samira Escopy; Yashapal Singh; Keith J Stine; Alexei V Demchenko
Journal:  Chemistry       Date:  2022-05-25       Impact factor: 5.020

  1 in total

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