Literature DB >> 23461434

Building biologics by chemical synthesis: practical preparation of di- and triantennary N-linked glycoconjugates.

Maciej A Walczak1, Joji Hayashida, Samuel J Danishefsky.   

Abstract

A unified strategy for the syntheses of bi- and triantennary fully sialylated N-glycans is described. The synthesis capitalizes on a global glycosylation strategy that delivers the desired undeca- and tetradecasaccharide in excellent yields. Finally, conjugation of the glycan to PSMA oligopeptide is described.

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Year:  2013        PMID： 23461434      PMCID： PMC3632434          DOI： 10.1021/ja401385v

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  16 in total

Review 1.  Synthesis of glycoproteins.

Authors:  Benjamin G Davis
Journal:  Chem Rev       Date:  2002-02       Impact factor: 60.622

Review 2.  Glycoprotein synthesis: an update.

Authors:  David P Gamblin; Eoin M Scanlan; Benjamin G Davis
Journal:  Chem Rev       Date:  2009-01       Impact factor: 60.622

3.  Free sialooligosaccharides found in the unfertilized eggs of a freshwater trout, Plecoglossus altivelis. A large storage pool of complex-type bi-, tri-, and tetraantennary sialooligosaccharides.

Authors:  K Ishii; M Iwasaki; S Inoue; P T Kenny; H Komura; Y Inoue
Journal:  J Biol Chem       Date:  1989-01-25       Impact factor: 5.157

4.  Crystal structure of prostate-specific membrane antigen, a tumor marker and peptidase.

Authors:  Mindy I Davis; Melanie J Bennett; Leonard M Thomas; Pamela J Bjorkman
Journal:  Proc Natl Acad Sci U S A       Date:  2005-04-18       Impact factor: 11.205

5.  Synthesis of an alpha-(2,3)-Sialylated, Complex-Type Undecasaccharide.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  2000-02       Impact factor: 15.336

6.  Chemical synthesis of normal and transformed PSA glycopeptides.

Authors:  Vadim Y Dudkin; Justin S Miller; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2004-01-28       Impact factor: 15.419

7.  Chemoselective ligation applied to the synthesis of a biantennary N-linked glycoform of CD52.

Authors:  Matthew R Pratt; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2003-05-21       Impact factor: 15.419

8.  Toward fully synthetic homogeneous beta-human follicle-stimulating hormone (beta-hFSH) with a biantennary N-linked dodecasaccharide. synthesis of beta-hFSH with chitobiose units at the natural linkage sites.

Authors:  Pavel Nagorny; Bernhard Fasching; Xuechen Li; Gong Chen; Baptiste Aussedat; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-04-29       Impact factor: 15.419

9.  Identification of the N-glycosylation sites on glutamate carboxypeptidase II necessary for proteolytic activity.

Authors:  Cyril Barinka; Pavel Sácha; Jan Sklenár; Petr Man; Karel Bezouska; Barbara S Slusher; Jan Konvalinka
Journal:  Protein Sci       Date:  2004-06       Impact factor: 6.725

Review 10.  Sialic acids as regulators of molecular and cellular interactions.

Authors:  Roland Schauer
Journal:  Curr Opin Struct Biol       Date:  2009-08-19       Impact factor: 6.809
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  7 in total

Review 1.  Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

Authors:  Matteo Panza; Salvatore G Pistorio; Keith J Stine; Alexei V Demchenko
Journal:  Chem Rev       Date:  2018-06-28       Impact factor: 60.622

2.  Chemoenzymatic Approach for the Preparation of Asymmetric Bi-, Tri-, and Tetra-Antennary N-Glycans from a Common Precursor.

Authors:  Ivan A Gagarinov; Tiehai Li; Javier Sastre Toraño; Tomislav Caval; Apoorva D Srivastava; John A W Kruijtzer; Albert J R Heck; Geert-Jan Boons
Journal:  J Am Chem Soc       Date:  2017-01-06       Impact factor: 15.419

3.  Decoding glycan protein interactions by a new class of asymmetric N-glycans.

Authors:  Zhigang Wu; Yunpeng Liu; Lei Li; Xiu-Feng Wan; He Zhu; Yuxi Guo; Mohui Wei; Wanyi Guan; Peng George Wang
Journal:  Org Biomol Chem       Date:  2017-10-31       Impact factor: 3.876

4.  Manual and Automated Syntheses of the N-Linked Glycoprotein Core Glycans.

Authors:  Salvatore G Pistorio; Scott A Geringer; Keith J Stine; Alexei V Demchenko
Journal:  J Org Chem       Date:  2019-05-17       Impact factor: 4.354

5.  Chemical synthesis of highly congested gp120 V1V2 N-glycopeptide antigens for potential HIV-1-directed vaccines.

Authors:  Baptiste Aussedat; Yusuf Vohra; Peter K Park; Alberto Fernández-Tejada; S Munir Alam; S Moses Dennison; Frederick H Jaeger; Kara Anasti; Shelley Stewart; Julie H Blinn; Hua-Xin Liao; Joseph G Sodroski; Barton F Haynes; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2013-08-22       Impact factor: 15.419

6.  Traceless Photolabile Linker Expedites the Chemical Synthesis of Complex Oligosaccharides by Automated Glycan Assembly.

Authors:  Kim Le Mai Hoang; Alonso Pardo-Vargas; Yuntao Zhu; Yang Yu; Mirco Loria; Martina Delbianco; Peter H Seeberger
Journal:  J Am Chem Soc       Date:  2019-05-24       Impact factor: 15.419

Review 7.  Recent Advances in the Chemical Biology of N-Glycans.

Authors:  Asuka Shirakawa; Yoshiyuki Manabe; Koichi Fukase
Journal:  Molecules       Date:  2021-02-16       Impact factor: 4.411
  7 in total

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