Literature DB >> 20738084

pH-dependent mutarotation of 1-thioaldoses in water. Unexpected behavior of (2s)-D-aldopyranoses.

Rémi Caraballo1, Lingquan Deng, Luis Amorim, Tore Brinck, Olof Ramström.   

Abstract

The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the β-anomer at lower pH to the α-anomer at higher pH.

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Year:  2010        PMID： 20738084     DOI： 10.1021/jo100826e

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  Characterization of Enzymes Catalyzing Transformations of Cysteine S-Conjugated Intermediates in the Lincosamide Biosynthetic Pathway.

Authors:  Richiro Ushimaru; Chia-I Lin; Eita Sasaki; Hung-Wen Liu
Journal:  Chembiochem       Date:  2016-07-19       Impact factor: 3.164

2.  Stereoselective synthesis of light-activatable perfluorophenylazide-conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging.

Authors:  Lingquan Deng; Oscar Norberg; Suji Uppalapati; Mingdi Yan; Olof Ramström
Journal:  Org Biomol Chem       Date:  2011-03-18       Impact factor: 3.876

3.  Stereocontrolled 1-S-glycosylation and comparative binding studies of photoprobe-thiosaccharide conjugates with their O-linked analogs.

Authors:  Lingquan Deng; Xin Wang; Suji Uppalapati; Oscar Norberg; Hai Dong; Adrien Joliton; Mingdi Yan; Olof Ramström
Journal:  Pure Appl Chem       Date:  2013-01       Impact factor: 2.453

4.  Photoinitiated Thiol-ene Reactions of Enoses: A Powerful Tool for Stereoselective Synthesis of Glycomimetics with Challenging Glycosidic Linkages.

Authors:  Anikó Borbás
Journal:  Chemistry       Date:  2020-03-19       Impact factor: 5.236
  4 in total

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