Literature DB >> 22780913

Automated solid-phase synthesis of hyaluronan oligosaccharides.

Marthe T C Walvoort1, Anne Geert Volbeda, Niels R M Reintjens, Hans van den Elst, Obadiah J Plante, Herman S Overkleeft, Gijsbert A van der Marel, Jeroen D C Codée.   

Abstract

Well-defined fragments of hyaluronic acid (HA) have been obtained through a fully automated solid-phase oligosaccharide synthesis. Disaccharide building blocks, featuring a disarmed glucuronic acid donor moiety and a di-tert-butylsilylidene-protected glucosamine part, were used in the rapid and efficient assembly of HA fragments up to the pentadecamer level, equipped with a conjugation-ready anomeric allyl function.

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Year:  2012        PMID： 22780913     DOI： 10.1021/ol301666n

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  16 in total

1.  Regioselective Benzylation of 2-Deoxy-2-Aminosugars Using Crown Ethers: Application to a Shortened Synthesis of Hyaluronic Acid Oligomers.

Authors:  Chinmoy Mukherjee; Lin Liu; Nicola L B Pohl
Journal:  Adv Synth Catal       Date:  2014-07-07       Impact factor: 5.837

2.  Fluorous-Tag-Assisted Synthesis of GAG-Like Oligosaccharides.

Authors:  José L de Paz; Pedro M Nieto
Journal:  Methods Mol Biol       Date:  2022

3.  Automated solid-phase synthesis of oligosaccharides containing sialic acids.

Authors:  Chian-Hui Lai; Heung Sik Hahm; Chien-Fu Liang; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2015-05-04       Impact factor: 2.883

4.  Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more.

Authors:  Marina Bantzi; Stephan Rigol; Athanassios Giannis
Journal:  Beilstein J Org Chem       Date:  2015-04-30       Impact factor: 2.883

5.  Automated glycan assembly of a S. pneumoniae serotype 3 CPS antigen.

Authors:  Markus W Weishaupt; Stefan Matthies; Mattan Hurevich; Claney L Pereira; Heung Sik Hahm; Peter H Seeberger
Journal:  Beilstein J Org Chem       Date:  2016-07-12       Impact factor: 2.883

Review 6.  Chemical O-Glycosylations: An Overview.

Authors:  Rituparna Das; Balaram Mukhopadhyay
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

7.  Cyanopivaloyl Ester in the Automated Solid-Phase Synthesis of Oligorhamnans.

Authors:  Anne Geert Volbeda; Jeanine van Mechelen; Nico Meeuwenoord; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  J Org Chem       Date:  2017-12-01       Impact factor: 4.354

8.  Total synthesis of TMG-chitotriomycin based on an automated electrochemical assembly of a disaccharide building block.

Authors:  Yuta Isoda; Norihiko Sasaki; Kei Kitamura; Shuji Takahashi; Sujit Manmode; Naoko Takeda-Okuda; Jun-Ichi Tamura; Toshiki Nokami; Toshiyuki Itoh
Journal:  Beilstein J Org Chem       Date:  2017-05-16       Impact factor: 2.883

9.  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

10.  P. aeruginosa SGNH hydrolase-like proteins AlgJ and AlgX have similar topology but separate and distinct roles in alginate acetylation.

Authors:  Perrin Baker; Tyler Ricer; Patrick J Moynihan; Elena N Kitova; Marthe T C Walvoort; Dustin J Little; John C Whitney; Karen Dawson; Joel T Weadge; Howard Robinson; Dennis E Ohman; Jeroen D C Codée; John S Klassen; Anthony J Clarke; P Lynne Howell
Journal:  PLoS Pathog       Date:  2014-08-28       Impact factor: 6.823
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