Literature DB >> 28318087

3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides.

Jing Zeng1, Guangfei Sun1, Wang Yao1, Yangbin Zhu1, Ruobin Wang1, Lei Cai1, Ke Liu1, Qian Zhang1, Xue-Wei Liu2, Qian Wan1,3.   

Abstract

A concise, diversity-oriented approach for the synthesis of naturally occurring 3-amino- and 3-nitro-2,3,6-trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3-aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different 3-aminosugar components using ortho-alkynylbenzoate donors.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  3-aminosugars; 3-nitrosugars; glycosylation; oligosaccharides; synthetic methods

Mesh：

Substances：

Year:  2017        PMID： 28318087     DOI： 10.1002/anie.201700178

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  7 in total

1.  Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks.

Authors:  Subbarao Yalamanchili; Tu-Anh Nguyen; Alexander Zsikla; Gavin Stamper; Ashley E DeYong; John Florek; Olivea Vasquez; Nicola L B Pohl; Clay S Bennett
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-21       Impact factor: 16.823

2.  Stereospecific Synthesis of the Saccharosamine-Rhamnose-Fucose Fragment Present in Saccharomicin B.

Authors:  Marissa Bylsma; Clay S Bennett
Journal:  Org Lett       Date:  2018-07-17       Impact factor: 6.005

3.  Rapid de Novo Preparation of 2,6-Dideoxy Sugar Libraries through Gold-Catalyzed Homopropargyl Orthoester Cyclization.

Authors:  Subbarao Yalamanchili; William Miller; Xizhao Chen; Clay S Bennett
Journal:  Org Lett       Date:  2019-11-22       Impact factor: 6.005

4.  Diversity-Oriented Synthesis and Chemoinformatic Analysis of the Molecular Diversity of sp3-Rich Morpholine Peptidomimetics.

Authors:  Elena Lenci; Riccardo Innocenti; Gloria Menchi; Andrea Trabocchi
Journal:  Front Chem       Date:  2018-10-30       Impact factor: 5.221

5.  The role of Chito-oligosaccharide in regulating ovarian germ stem cells function and restoring ovarian function in chemotherapy mice.

Authors:  Yaoqi Huang; Haifeng Ye; Feiyin Zhu; Chuan Hu; Yuehui Zheng
Journal:  Reprod Biol Endocrinol       Date:  2021-01-25       Impact factor: 5.211

6.  Synthetic (N,N-Dimethyl)doxorubicin Glycosyl Diastereomers to Dissect Modes of Action of Anthracycline Anticancer Drugs.

Authors:  Dennis P A Wander; Sabina Y van der Zanden; Merijn B L Vriends; Branca C van Veen; Joey G C Vlaming; Thomas Bruyning; Thomas Hansen; Gijsbert A van der Marel; Herman S Overkleeft; Jacques J C Neefjes; Jeroen D C Codée
Journal:  J Org Chem       Date:  2021-03-30       Impact factor: 4.354

7.  Reactivity-Stereoselectivity Mapping for the Assembly of Mycobacterium marinum Lipooligosaccharides.

Authors:  Thomas Hansen; Tim P Ofman; Joey G C Vlaming; Ivan A Gagarinov; Jessey van Beek; Tessa A Goté; Jacoba M Tichem; Gijs Ruijgrok; Herman S Overkleeft; Dmitri V Filippov; Gijsbert A van der Marel; Jeroen D C Codée
Journal:  Angew Chem Int Ed Engl       Date:  2020-11-03       Impact factor: 16.823
  7 in total

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