Literature DB >> 24038615

Chemical diversification of sialic acid glycosides by stereospecific, chemoselective deamination.

Chandrasekhar Navuluri1, David Crich.   

Abstract

Late bloomer: Nitrosation of peracetylated sialic acid glycosides followed by treatment with sodium trifluoroethoxide and then a suitable nucleophile enables the late-stage modification of these glycosides with stereospecific replacement of the acetamido group. This method should enable access to many glycoside derivatives with a minimum of synthetic effort.
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  deamination; diversification; glycosylation; nitrosation; sialic acids

Mesh：

Substances：

Year:  2013        PMID： 24038615      PMCID： PMC3865865          DOI： 10.1002/anie.201303781

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


  15 in total

1.  Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.

Authors:  David Crich; Chandrasekhar Navuluri
Journal:  Angew Chem Int Ed Engl       Date:  2010-04-12       Impact factor: 15.336

2.  Highly alpha-selective sialyl phosphate donors for efficient preparation of natural sialosides.

Authors:  Che-Hsiung Hsu; Kuo-Ching Chu; Yih-Shyan Lin; Jeng-Liang Han; Yu-Shiang Peng; Chien-Tai Ren; Chung-Yi Wu; Chi-Huey Wong
Journal:  Chemistry       Date:  2010-02-08       Impact factor: 5.236

3.  The emergence of thiol-ene coupling as a click process for materials and bioorganic chemistry.

Authors:  Alessandro Dondoni
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Stereoselective synthesis of oligo-alpha-(2,8)-sialic acids.

Authors:  Hiroshi Tanaka; Yuji Nishiura; Takashi Takahashi
Journal:  J Am Chem Soc       Date:  2006-06-07       Impact factor: 15.419

5.  O-sialylation with N-acetyl-5-n,4-o-carbonyl-protected thiosialoside donors in dichloromethane: facile and selective cleavage of the oxazolidinone ring.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-03-06       Impact factor: 4.354

6.  Click and pick: identification of sialoside analogues for siglec-based cell targeting.

Authors:  Cory D Rillahan; Erik Schwartz; Ryan McBride; Valery V Fokin; James C Paulson
Journal:  Angew Chem Int Ed Engl       Date:  2012-10-04       Impact factor: 15.336

Review 7.  C-5 modifications in N-acetyl-neuraminic acid: scope and limitations.

Authors:  Cristina De Meo; Uvege Priyadarshani
Journal:  Carbohydr Res       Date:  2008-04-10       Impact factor: 2.104

8.  alpha-selective sialylations at -78 degrees C in nitrile solvents with a 1-adamantanyl thiosialoside.

Authors:  David Crich; Wenju Li
Journal:  J Org Chem       Date:  2007-09-07       Impact factor: 4.354

9.  Synthesis of S-linked alpha(2-->9) octasialic acid via exclusive alpha S-glycosidic bond formation.

Authors:  Chien-Fu Liang; Ming-Chung Yan; Tsung-Che Chang; Chun-Cheng Lin
Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

10.  Stereoselective Synthesis of alpha(2,9) Di- to Tetrasialic Acids, Using a 5,4-N,O-Carbonyl Protected Thiosialoside.

Authors:  Hiroshi Tanaka; Yuji Nishiura; Takashi Takahashi
Journal:  J Org Chem       Date:  2009-06-05       Impact factor: 4.354
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  5 in total

1.  Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination of N-Acetyl Neuraminic Acid: Isolation and Characterization of Tricyclic 3-Keto-2-deoxy-nonulosonic Acid (KDN) Derivatives via an Intermediate Vinyl Diazonium Ion.

Authors:  Mohammed Hawsawi; Anura Wickramasinghe; David Crich
Journal:  J Org Chem       Date:  2019-10-29       Impact factor: 4.354

2.  Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-epi-Acetaminic Acid, and 8-epi-Legionaminic Acid Glycosyl Donors from N-Acetylneuraminic Acid by Side Chain Exchange.

Authors:  Sameera Siyabalapitiya Arachchige; David Crich
Journal:  Org Lett       Date:  2022-04-14       Impact factor: 6.072

3.  Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.

Authors:  Bibek Dhakal; David Crich
Journal:  J Am Chem Soc       Date:  2018-10-25       Impact factor: 15.419

4.  Use of hydroxylamines, hydroxamic acids, oximes and amines as nucleophiles in the Zbiral oxidative deamination of N-acetyl neuraminic acid. Isolation and characterization of novel mono- and disubstitution products.

Authors:  Mohammed Hawsawi; Michael G Pirrone; Anura Wickramasinghe; David Crich
Journal:  Carbohydr Res       Date:  2020-01-25       Impact factor: 2.104

5.  Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction.

Authors:  Jih Ru Hwu; D Balaji Chandrasekhar; Kuo Chu Hwang; Chun-Cheng Lin; Jia-Cherng Horng; Fa-Kuen Shieh
Journal:  ChemistryOpen       Date:  2017-05-05       Impact factor: 2.911
  5 in total

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