Literature DB >> 30641292

Recent advances in reagent-controlled stereoselective/stereospecific glycosylation.

Hui Yao1, Minh Duy Vu1, Xue-Wei Liu2.   

Abstract

The formation of O-glycosidic linkage is arguably one of the most important topics in glycoscience due to the prevalence of O-glycosides in nature. Great efforts have been devoted to this field by many carbohydrate chemists to develop stereoselective/stereospecific glycosylation methodologies. Although glycosyl donor- and acceptor-controlled strategies have significantly progressed, the tedious design and pre-synthesis of substrates could not be avoided. On the other hand, reagent-controlled glycosylation can overcome these challenges and produce the desired selectivity by only altering external factors such as concentration, reagents or other reaction conditions. This mini-review discusses selected recent novel methodologies on reagent-mediated stereo-controlled glycosylation in the last decade, classified by the types of glycosyl donors.
Copyright © 2018. Published by Elsevier Ltd.

Entities:  

Keywords:  Glycosylation; Reagent-control; Stereoselectivity; Stereospecificity

Mesh:

Substances:

Year:  2018        PMID: 30641292     DOI: 10.1016/j.carres.2018.10.006

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  8 in total

1.  Mimicry of the proton wire mechanism of enzymes inside a supramolecular capsule enables β-selective O-glycosylations.

Authors:  Tian-Ren Li; Fabian Huck; GiovanniMaria Piccini; Konrad Tiefenbacher
Journal:  Nat Chem       Date:  2022-07-07       Impact factor: 24.274

Review 2.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

Authors:  Mana Mohan Mukherjee; Rina Ghosh; John A Hanover
Journal:  Front Mol Biosci       Date:  2022-06-14

3.  Metabolic engineering of yeasts for green and sustainable production of bioactive ginsenosides F2 and 3β,20S-Di-O-Glc-DM.

Authors:  Fenglin Jiang; Chen Zhou; Yan Li; Haidong Deng; Ting Gong; Jingjing Chen; Tianjiao Chen; Jinling Yang; Ping Zhu
Journal:  Acta Pharm Sin B       Date:  2022-04-27       Impact factor: 14.903

4.  Hydrogen bond activated glycosylation under mild conditions.

Authors:  Ke Xiao; Yongxin Hu; Yongyong Wan; XinXin Li; Qin Nie; Hao Yan; Liming Wang; Jinxi Liao; Deyong Liu; Yuanhong Tu; Jiansong Sun; Jeroen D C Codée; Qingju Zhang
Journal:  Chem Sci       Date:  2021-12-15       Impact factor: 9.825

5.  Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-trans glycosides and (1→6)-linked disaccharides of 2-acetamido sugars.

Authors:  Xin Qiu; Anna L Garden; Antony J Fairbanks
Journal:  Chem Sci       Date:  2022-03-17       Impact factor: 9.825

Review 6.  Recent advances in stereoselective 1,2-cis-O-glycosylations.

Authors:  Akihiro Ishiwata; Katsunori Tanaka; Jiaming Ao; Feiqing Ding; Yukishige Ito
Journal:  Front Chem       Date:  2022-08-19       Impact factor: 5.545

7.  Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group.

Authors:  Wenjing Ye; Christopher M Stevens; Peng Wen; Christopher J Simmons; Weiping Tang
Journal:  J Org Chem       Date:  2020-08-05       Impact factor: 4.354

8.  Automated Assembly of Starch and Glycogen Polysaccharides.

Authors:  Yuntao Zhu; Martina Delbianco; Peter H Seeberger
Journal:  J Am Chem Soc       Date:  2021-06-11       Impact factor: 15.419

  8 in total

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