Literature DB >> 24473737

Synthesis of the tumor associative α-aminooxy disaccharide of the TF antigen and its conjugation to a polysaccharide immune stimulant.

Jean Paul Bourgault1, Kevin R Trabbic, Mengchao Shi, Peter R Andreana.   

Abstract

The α-aminooxy derivative of the Thomsen-Friedenriech tumor associated carbohydrate antigen has been synthesized in 11 steps utilizing a D-GalN3 acceptor carrying a pre-installed α-N-hydroxysuccinimidyl moiety. The natural α linkage was prepared in high selectivity employing a suitably protected D-GalN3-thioglycoside donor with N-hydroxysuccinimide. With access to α-TF-ONH2, the preparation of the TF-PS A1 vaccine candidate ensued smoothly through oxime bond formation.

Entities:  

Mesh：

Substances：

Year:  2014        PMID： 24473737      PMCID： PMC3956868          DOI： 10.1039/c4ob00128a

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  28 in total

1.  Synthesis of oxime-linked mucin mimics containing the tumor-related T(N) and sialyl T(N) antigens.

Authors:  L A Marcaurelle; Y Shin; S Goon; C R Bertozzi
Journal:  Org Lett       Date:  2001-11-15       Impact factor: 6.005

2.  Immunological response from an entirely carbohydrate antigen: design of synthetic vaccines based on Tn-PS A1 conjugates.

Authors:  Ravindra A De Silva; Qianli Wang; Tristan Chidley; Dananjaya K Appulage; Peter R Andreana
Journal:  J Am Chem Soc       Date:  2009-07-22       Impact factor: 15.419

3.  5-N,4-O-carbonyl-7,8,9-tri-O-chloroacetyl-protected sialyl donor for the stereoselective synthesis of alpha-(2-->9)-tetrasialic acid.

Authors:  Chang-Ching Lin; Nai-Pin Lin; L Sk Sahabuddin; Vijaya Raghava Reddy; Li-De Huang; Kuo Chu Hwang; Chun-Cheng Lin
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

4.  T/Tn antigen vaccine is effective and safe in preventing recurrence of advanced breast carcinoma.

Authors:  G F Springer; P R Desai; B D Spencer; H Tegtmeyer; S C Carlstedt; E F Scanlon
Journal:  Cancer Detect Prev       Date:  1995

5.  One-pot synthesis of sialo-containing glycosyl amino acids by use of an N-trichloroethoxycarbonyl-beta-thiophenyl sialoside.

Authors:  Hiroshi Tanaka; Masaatsu Adachi; Takashi Takahashi
Journal:  Chemistry       Date:  2005-01-21       Impact factor: 5.236

6.  Highly efficient preparation of tumor antigen-containing glycopeptide building blocks from novel pentenyl glycosides.

Authors:  Serge A Svarovsky; Joseph J Barchi
Journal:  Carbohydr Res       Date:  2003-09-10       Impact factor: 2.104

7.  Influence of the 4,6-O-benzylidene, 4,6-O-phenylboronate, and 4,6-O-polystyrylboronate protecting groups on the stereochemical outcome of thioglycoside-based glycosylations mediated by 1-benzenesulfinyl piperidine/triflic anhydride and N-iodosuccinimide/trimethylsilyl triflate.

Authors:  David Crich; Marco de la Mora; A U Vinod
Journal:  J Org Chem       Date:  2003-10-17       Impact factor: 4.354

8.  Polysaccharide processing and presentation by the MHCII pathway.

Authors:  Brian A Cobb; Qun Wang; Arthur O Tzianabos; Dennis L Kasper
Journal:  Cell       Date:  2004-05-28       Impact factor: 41.582

9.  Protein glycoengineering enabled by the versatile synthesis of aminooxy glycans and the genetically encoded aldehyde tag.

Authors:  Jason E Hudak; Helen H Yu; Carolyn R Bertozzi
Journal:  J Am Chem Soc       Date:  2011-09-14       Impact factor: 15.419

Review 10.  The Tn antigen-structural simplicity and biological complexity.

Authors:  Tongzhong Ju; Vivianne I Otto; Richard D Cummings
Journal:  Angew Chem Int Ed Engl       Date:  2011-01-21       Impact factor: 15.336
View more
  8 in total

1.  Synthesis of an Aminooxy Derivative of the GM3 Antigen and Its Application in Oxime Ligation.

Authors:  Kristopher A Kleski; Mengchao Shi; Matthew Lohman; Gabrielle T Hymel; Vinod K Gattoji; Peter R Andreana
Journal:  J Org Chem       Date:  2020-05-01       Impact factor: 4.354

2.  Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides.

Authors:  Eric T Sletten; Sai Kumar Ramadugu; Hien M Nguyen
Journal:  Carbohydr Res       Date:  2016-10-24       Impact factor: 2.104

3.  Elucidating Structural Features of an Entirely Carbohydrate Cancer Vaccine Construct Employing Circular Dichroism and Fluorescent Labeling.

Authors:  Kevin R Trabbic; Ravindra A De Silva; Peter R Andreana
Journal:  Medchemcomm       Date:  2014-08-01       Impact factor: 3.597

4.  Synthesis of an Aminooxy Derivative of the Trisaccharide Globotriose Gb3.

Authors:  Samir Ghosh; Peter R Andreana
Journal:  J Carbohydr Chem       Date:  2014-09-01       Impact factor: 1.667

5.  Probing the influence of protecting groups on the anomeric equilibrium in sialic acid glycosides with the persistent radical effect.

Authors:  Pavan K Kancharla; Takayuki Kato; David Crich
Journal:  J Am Chem Soc       Date:  2014-04-01       Impact factor: 15.419

Review 6.  Entirely Carbohydrate-Based Vaccines: An Emerging Field for Specific and Selective Immune Responses.

Authors:  Sharmeen Nishat; Peter R Andreana
Journal:  Vaccines (Basel)       Date:  2016-05-20

7.  Glycoamino Acid Analogues of the Thomsen-Friedenreich Tumor-Associated Carbohydrate Antigen: Synthesis and Evaluation of Novel Antiproliferative Factor Glycopeptides.

Authors:  Maqbool A Siddiqui; Shailesh Ambre; Susan K Keay; Jeffrey M Rhyne; Chen-Ou Zhang; Joseph J Barchi
Journal:  ACS Omega       Date:  2017-09-08

8.  Enhanced Immune Response Against the Thomsen-Friedenreich Tumor Antigen Using a Bivalent Entirely Carbohydrate Conjugate.

Authors:  Kristopher A Kleski; Kevin R Trabbic; Mengchao Shi; Jean-Paul Bourgault; Peter R Andreana
Journal:  Molecules       Date:  2020-03-13       Impact factor: 4.411
  8 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.