Literature DB >> 32516600

Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide.

Katie A Rykaczewski1, Kate E Sabourin1, Paul J Goo1, Lydia H Griggs1, Saumya Jain1, Paxton A M Reed1, Joseph M Langenhan2.   

Abstract

Herein, we report the first selective anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a competent reagent in the solid-phase peptide synthesis of N-linked glycopeptides.
Copyright © 2020 Elsevier Ltd. All rights reserved.

Entities:  

Mesh:

Substances:

Year:  2020        PMID: 32516600      PMCID: PMC7325706          DOI: 10.1016/j.carres.2020.108022

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


  19 in total

1.  Rotamers or diastereomers? An overlooked NMR solution.

Authors:  Dennis X Hu; Peter Grice; Steven V Ley
Journal:  J Org Chem       Date:  2012-05-22       Impact factor: 4.354

Review 2.  Neoglycorandomization and chemoenzymatic glycorandomization: two complementary tools for natural product diversification.

Authors:  Joseph M Langenhan; Byron R Griffith; Jon S Thorson
Journal:  J Nat Prod       Date:  2005-11       Impact factor: 4.050

3.  An efficient synthetic route to glycoamino acid building blocks for glycopeptide synthesis.

Authors:  Mallesham Bejugam; Sabine L Flitsch
Journal:  Org Lett       Date:  2004-10-28       Impact factor: 6.005

Review 4.  Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.

Authors:  Lai-Xi Wang; Mohammed N Amin
Journal:  Chem Biol       Date:  2014-01-16

5.  Enhancing the anticancer properties of cardiac glycosides by neoglycorandomization.

Authors:  Joseph M Langenhan; Noël R Peters; Ilia A Guzei; F Michael Hoffmann; Jon S Thorson
Journal:  Proc Natl Acad Sci U S A       Date:  2005-08-16       Impact factor: 11.205

6.  Convergent Synthesis of N-Linked Glycopeptides via Aminolysis of ω-Asp p-Nitrophenyl Thioesters in Solution.

Authors:  Jing-Jing Du; Xiao-Fei Gao; Ling-Ming Xin; Ze Lei; Zheng Liu; Jun Guo
Journal:  Org Lett       Date:  2016-09-13       Impact factor: 6.005

7.  Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of alpha-substituted alpha-cyanoacetates and beta-dicarbonyl compounds.

Authors:  Steen Saaby; Marco Bella; Karl Anker Jørgensen
Journal:  J Am Chem Soc       Date:  2004-07-07       Impact factor: 15.419

8.  Stereoselective N-glycosylation by Staudinger ligation.

Authors:  Yi He; Ronald J Hinklin; Jiyoung Chang; Laura L Kiessling
Journal:  Org Lett       Date:  2004-11-25       Impact factor: 6.005

Review 9.  Emerging principles for the therapeutic exploitation of glycosylation.

Authors:  Martin Dalziel; Max Crispin; Christopher N Scanlan; Nicole Zitzmann; Raymond A Dwek
Journal:  Science       Date:  2014-01-03       Impact factor: 47.728

10.  Fucose, mannose, and β-N-acetylglucosamine glycopolymers initiate the mouse sperm acrosome reaction through convergent signaling pathways.

Authors:  Linghui Wu; Nicole S Sampson
Journal:  ACS Chem Biol       Date:  2013-11-25       Impact factor: 5.100

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.