Literature DB >> 33351642

Long-Range Stereodirecting Participation across a Glycosidic Linkage in Glycosylation Reactions.

Weizhun Yang, Jicheng Zhang, Chia-Wei Yang, Sherif Ramadan1, Richard Staples, Xuefei Huang.   

Abstract

The formation of an unprecedented 12-membered macrocyclic ketal through the long-range participation of a levulinoyl group across a glycosidic linkage was observed in glycosylation reactions. This finding indicated that stereodirecting participation is not limited to groups within the glycan ring being activated, thus broadening the scope of remote group participation in glycosylation.

Entities:  

Mesh：

Substances：

Year:  2020        PMID： 33351642      PMCID： PMC8120453          DOI： 10.1021/acs.orglett.0c03394

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


  25 in total

1.  Iterative one-pot synthesis of oligosaccharides.

Authors:  Xuefei Huang; Lijun Huang; Haisheng Wang; Xin-Shan Ye
Journal:  Angew Chem Int Ed Engl       Date:  2004-10-04       Impact factor: 15.336

2.  A general strategy for stereoselective glycosylations.

Authors:  Jin-Hwan Kim; Hai Yang; Jin Park; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2005-08-31       Impact factor: 15.419

3.  Installation of electron-donating protective groups, a strategy for glycosylating unreactive thioglycosyl acceptors using the preactivation-based glycosylation method.

Authors:  Youlin Zeng; Zhen Wang; Dennis Whitfield; Xuefei Huang
Journal:  J Org Chem       Date:  2008-09-23       Impact factor: 4.354

4.  Chemical synthesis of syndecan-3 glycopeptides bearing two heparan sulfate glycan chains.

Authors:  Keisuke Yoshida; Bo Yang; Weizhun Yang; Zeren Zhang; Jicheng Zhang; Xuefei Huang
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-30       Impact factor: 15.336

Review 5.  The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1-SN2 Interface.

Authors:  Philip Ouma Adero; Harsha Amarasekara; Peng Wen; Luis Bohé; David Crich
Journal:  Chem Rev       Date:  2018-05-30       Impact factor: 60.622

6.  Synthesis of Chondroitin Sulfate A Bearing Syndecan-1 Glycopeptide.

Authors:  Sherif Ramadan; Weizhun Yang; Zeren Zhang; Xuefei Huang
Journal:  Org Lett       Date:  2017-08-29       Impact factor: 6.005

Review 7.  Acceptor reactivity in glycosylation reactions.

Authors:  Stefan van der Vorm; Thomas Hansen; Jacob M A van Hengst; Herman S Overkleeft; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Chem Soc Rev       Date:  2019-08-27       Impact factor: 54.564

Review 8.  Design of α-Selective Glycopyranosyl Donors Relying on Remote Anchimeric Assistance.

Authors:  Bozhena S Komarova; Yury E Tsvetkov; Nikolay E Nifantiev
Journal:  Chem Rec       Date:  2016-01-20       Impact factor: 6.771

9.  Evidence of robust participation by an equatorial 4-O group in glycosylation on a 2-azido-2-deoxy-glucopyranosyl donor.

Authors:  Dongming Yao; Yichu Liu; Shiqiang Yan; Yingxia Li; Chun Hu; Ning Ding
Journal:  Chem Commun (Camb)       Date:  2017-03-07       Impact factor: 6.222

10.  Does neighboring group participation by non-vicinal esters play a role in glycosylation reactions? Effective probes for the detection of bridging intermediates.

Authors:  David Crich; Tianshun Hu; Feng Cai
Journal:  J Org Chem       Date:  2008-10-22       Impact factor: 4.354
View more
  2 in total

1.  Direct Experimental Characterization of a Bridged Bicyclic Glycosyl Dioxacarbenium Ion by 1 H and 13 C NMR Spectroscopy: Importance of Conformation on Participation by Distal Esters.

Authors:  Kapil Upadhyaya; Yagya P Subedi; David Crich
Journal:  Angew Chem Int Ed Engl       Date:  2021-10-21       Impact factor: 15.336

2.  Stabilization of Glucosyl Dioxolenium Ions by "Dual Participation" of the 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Protection Group for 1,2-cis-Glucosylation.

Authors:  Wouter A Remmerswaal; Kas J Houthuijs; Roel van de Ven; Hidde Elferink; Thomas Hansen; Giel Berden; Herman S Overkleeft; Gijsbert A van der Marel; Floris P J T Rutjes; Dmitri V Filippov; Thomas J Boltje; Jonathan Martens; Jos Oomens; Jeroen D C Codée
Journal:  J Org Chem       Date:  2022-06-24       Impact factor: 4.198
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.