Literature DB >> 22954207

Solving the convergence problem in the synthesis of triantennary N-glycan relevant to prostate-specific membrane antigen (PSMA).

Maciej A Walczak1, Samuel J Danishefsky.   

Abstract

The first total synthesis of triantennary, fully sialylated N-glycan of complex type is described. Two strategies for installation of sialylated antennae are explored, and both approaches converge on a global glycosylation step that delivers the desired tetradecasaccharide in good yields.

Entities:  

Mesh：

Substances：

Year:  2012        PMID： 22954207      PMCID： PMC3470013          DOI： 10.1021/ja307628w

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


  31 in total

1.  A chemically induced vaccine strategy for prostate cancer.

Authors:  Anna Dubrovska; Chanhyuk Kim; Jimmy Elliott; Weijun Shen; Tun-Hsun Kuo; Dong-In Koo; Chun Li; Tove Tuntland; Jonathan Chang; Todd Groessl; Xu Wu; Vanessa Gorney; Teresa Ramirez-Montagut; David A Spiegel; Charles Y Cho; Peter G Schultz
Journal:  ACS Chem Biol       Date:  2011-09-21       Impact factor: 5.100

2.  Use of fluorobenzoyl protective groups in synthesis of glycopeptides: beta-elimination of O-linked carbohydrates is suppressed.

Authors:  P Sjölin; J Kihlberg
Journal:  J Org Chem       Date:  2001-05-04       Impact factor: 4.354

3.  Glycosylation using a one-electron-transfer, homogeneous reagent. Application to an efficient synthesis of the trimannosyl core of N-glycosylproteins.

Authors:  Y M Zhang; J M Mallet; P Sinaÿ
Journal:  Carbohydr Res       Date:  1992-12-15       Impact factor: 2.104

4.  Direct synthesis of beta-mannans. A hexameric [-->3)-beta-D-Man-(1](3) subunit of the antigenic polysaccharides from Leptospira biflexa and the octameric (1-->2)-linked beta-D-mannan of the Candida albicans phospholipomannan. X-ray crystal structure of a protected tetramer.

Authors:  D Crich; H Li; Q Yao; D J Wink; R D Sommer; A L Rheingold
Journal:  J Am Chem Soc       Date:  2001-06-20       Impact factor: 15.419

5.  Isolation and structure determination of the intact sialylated N-linked carbohydrate chains of recombinant human follitropin expressed in Chinese hamster ovary cells.

Authors:  K Hård; A Mekking; J B Damm; J P Kamerling; W de Boer; R A Wijnands; J F Vliegenthart
Journal:  Eur J Biochem       Date:  1990-10-05

6.  Total synthesis of the 2,6-sialylated immunoglobulin G glycopeptide fragment in homogeneous form.

Authors:  Ping Wang; Jianglong Zhu; Yu Yuan; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-11-25       Impact factor: 15.419

7.  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

8.  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

9.  Prostate-specific membrane antigen targeted imaging and therapy of prostate cancer using a PSMA inhibitor as a homing ligand.

Authors:  Sumith A Kularatne; Kevin Wang; Hari-Krishna R Santhapuram; Philip S Low
Journal:  Mol Pharm       Date:  2009 May-Jun       Impact factor: 4.939

Review 10.  Synthetic carbohydrate-based anticancer vaccines: the Memorial Sloan-Kettering experience.

Authors:  Jianglong Zhu; J David Warren; Samuel J Danishefsky
Journal:  Expert Rev Vaccines       Date:  2009-10       Impact factor: 5.217
View more
  13 in total

1.  A general strategy for the chemoenzymatic synthesis of asymmetrically branched N-glycans.

Authors:  Zhen Wang; Zoeisha S Chinoy; Shailesh G Ambre; Wenjie Peng; Ryan McBride; Robert P de Vries; John Glushka; James C Paulson; Geert-Jan Boons
Journal:  Science       Date:  2013-07-26       Impact factor: 47.728

2.  Chemical biology of glycoproteins: From chemical synthesis to biological impact.

Authors:  Yaohao Li; Amy H Tran; Samuel J Danishefsky; Zhongping Tan
Journal:  Methods Enzymol       Date:  2019-03-14       Impact factor: 1.600

3.  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

4.  Endo-F3 Glycosynthase Mutants Enable Chemoenzymatic Synthesis of Core-fucosylated Triantennary Complex Type Glycopeptides and Glycoproteins.

Authors:  John P Giddens; Joseph V Lomino; Mohammed N Amin; Lai-Xi Wang
Journal:  J Biol Chem       Date:  2016-03-10       Impact factor: 5.157

Review 5.  Chemical and chemoenzymatic synthesis of glycoproteins for deciphering functions.

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

6.  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

7.  Chemoenzymatic Synthesis of Asymmetrical Multi-Antennary N-Glycans to Dissect Glycan-Mediated Interactions between Human Sperm and Oocytes.

Authors:  Zoeisha S Chinoy; Frédéric Friscourt; Chantelle J Capicciotti; Philip Chiu; Geert-Jan Boons
Journal:  Chemistry       Date:  2018-05-09       Impact factor: 5.236

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

Authors:  Maciej A Walczak; Joji Hayashida; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2013-03-19       Impact factor: 15.419

9.  Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library.

Authors:  Lei Li; Yunpeng Liu; Cheng Ma; Jingyao Qu; Angie D Calderon; Baolin Wu; Na Wei; Xuan Wang; Yuxi Guo; Zhongying Xiao; Jing Song; Go Sugiarto; Yanhong Li; Hai Yu; Xi Chen; Peng George Wang
Journal:  Chem Sci       Date:  2015-06-23       Impact factor: 9.825

10.  Catalyst recognition of cis-1,2-diols enables site-selective functionalization of complex molecules.

Authors:  Xixi Sun; Hyelee Lee; Sunggi Lee; Kian L Tan
Journal:  Nat Chem       Date:  2013-08-11       Impact factor: 24.427
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.