Literature DB >> 19874068

A practical total synthesis of globo-H for use in anticancer vaccines.

Insik Jeon1, Karthik Iyer, Samuel J Danishefsky.   

Abstract

An improved synthesis of the hexasaccharide MBr1 antigen (globo-H) is reported. Enhanced efficiency in the synthesis was necessary for the scale-up production of globo-H, in order to advance globo-H-based anticancer vaccines to clinical trials. The key features of the improved synthesis include preactivation-based glycosylations and a revised iodosulfonimidation/rearrangement.

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Year:  2009        PMID: 19874068      PMCID: PMC3016894          DOI: 10.1021/jo901682p

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  24 in total

1.  A Two-Directional and Highly Convergent Approach for the Synthesis of the Tumor-Associated Antigen Globo-H.

Authors: 
Journal:  Angew Chem Int Ed Engl       Date:  1999-12-03       Impact factor: 15.336

2.  Preparation and evaluation of unimolecular pentavalent and hexavalent antigenic constructs targeting prostate and breast cancer: a synthetic route to anticancer vaccine candidates.

Authors:  Govind Ragupathi; Fusataka Koide; Philip O Livingston; Young Shin Cho; Atsushi Endo; Qian Wan; Maria K Spassova; Stacy J Keding; Jennifer Allen; Ouathek Ouerfelli; Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

3.  Most early disseminated cancer cells detected in bone marrow of breast cancer patients have a putative breast cancer stem cell phenotype.

Authors:  Marija Balic; Henry Lin; Lillian Young; Debra Hawes; Armando Giuliano; George McNamara; Ram H Datar; Richard J Cote
Journal:  Clin Cancer Res       Date:  2006-10-01       Impact factor: 12.531

4.  Selection of tumor antigens as targets for immune attack using immunohistochemistry: II. Blood group-related antigens.

Authors:  S Zhang; H S Zhang; C Cordon-Cardo; V E Reuter; A K Singhal; K O Lloyd; P O Livingston
Journal:  Int J Cancer       Date:  1997-09-26       Impact factor: 7.396

5.  Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3.

Authors:  Folkert Bosse; Lisa A Marcaurelle; Peter H Seeberger
Journal:  J Org Chem       Date:  2002-09-20       Impact factor: 4.354

6.  Expression of Globo H and SSEA3 in breast cancer stem cells and the involvement of fucosyl transferases 1 and 2 in Globo H synthesis.

Authors:  Wen-Wei Chang; Chien Hsin Lee; Peishan Lee; Juway Lin; Chun-Wei Hsu; Jung-Tung Hung; Jin-Jin Lin; Jyh-Cherng Yu; Li-en Shao; John Yu; Chi-Huey Wong; Alice L Yu
Journal:  Proc Natl Acad Sci U S A       Date:  2008-08-06       Impact factor: 11.205

7.  New globoseries glycosphingolipids in human teratocarcinoma reactive with the monoclonal antibody directed to a developmentally regulated antigen, stage-specific embryonic antigen 3.

Authors:  R Kannagi; S B Levery; F Ishigami; S Hakomori; L H Shevinsky; B B Knowles; D Solter
Journal:  J Biol Chem       Date:  1983-07-25       Impact factor: 5.157

8.  Multi-component one-pot synthesis of the tumor-associated carbohydrate antigen Globo-H based on preactivation of thioglycosyl donors.

Authors:  Zhen Wang; Luyuan Zhou; Kheireddine El-Boubbou; Xin-shan Ye; Xuefei Huang
Journal:  J Org Chem       Date:  2007-07-21       Impact factor: 4.354

9.  Generation of monoclonal antibodies reacting with normal and cancer cells of human breast.

Authors:  S Mènard; E Tagliabue; S Canevari; G Fossati; M I Colnaghi
Journal:  Cancer Res       Date:  1983-03       Impact factor: 12.701

10.  Biologics through chemistry: total synthesis of a proposed dual-acting vaccine targeting ovarian cancer by orchestration of oligosaccharide and polypeptide domains.

Authors:  Jianglong Zhu; Qian Wan; Govind Ragupathi; Constantine M George; Philip O Livingston; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2009-03-25       Impact factor: 15.419

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  10 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.  Antibody repertoire profiling with mimotope arrays.

Authors:  Shina Pashova; Christoph Schneider; Stephan von Gunten; Anastas Pashov
Journal:  Hum Vaccin Immunother       Date:  2016-12-08       Impact factor: 3.452

3.  Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans.

Authors:  Hai Yu; Yanhong Li; Jie Zeng; Vireak Thon; Dung M Nguyen; Thao Ly; Hui Yu Kuang; Alice Ngo; Xi Chen
Journal:  J Org Chem       Date:  2016-10-24       Impact factor: 4.354

4.  On orthogonal and selective activation of glycosyl thioimidates and thioglycosides: application to oligosaccharide assembly.

Authors:  Sophon Kaeothip; Alexei V Demchenko
Journal:  J Org Chem       Date:  2011-08-17       Impact factor: 4.354

5.  Affinity of monoclonal antibodies for Globo-series glycans.

Authors:  Chelcie H Eller; Guangbin Yang; Ouathek Ouerfelli; Ronald T Raines
Journal:  Carbohydr Res       Date:  2014-07-14       Impact factor: 2.104

6.  A vision for vaccines built from fully synthetic tumor-associated antigens: from the laboratory to the clinic.

Authors:  Rebecca M Wilson; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2013-09-18       Impact factor: 15.419

7.  ABO Antigens Active Tri- and Disaccharides Microarray to Evaluate C-type Lectin Receptor Binding Preferences.

Authors:  Chethan D Shanthamurthy; Prashant Jain; Sharon Yehuda; João T Monteiro; Shani Leviatan Ben-Arye; Balamurugan Subramani; Bernd Lepenies; Vered Padler-Karavani; Raghavendra Kikkeri
Journal:  Sci Rep       Date:  2018-04-26       Impact factor: 4.379

8.  2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis.

Authors:  Hemali D Premathilake; Alexei V Demchenko
Journal:  Beilstein J Org Chem       Date:  2012-04-18       Impact factor: 2.883

9.  Human Cancer Antigen Globo H Is a Cell-Surface Ligand for Human Ribonuclease 1.

Authors:  Chelcie H Eller; Tzu-Yuan Chao; Kiran K Singarapu; Ouathek Ouerfelli; Guangbin Yang; John L Markley; Samuel J Danishefsky; Ronald T Raines
Journal:  ACS Cent Sci       Date:  2015-07-13       Impact factor: 14.553

10.  Synthesis of Azido-Globo H Analogs for Immunogenicity Evaluation.

Authors:  Chiang-Yun Chen; Yu-Wei Lin; Szu-Wen Wang; Yung-Chu Lin; Yang-Yu Cheng; Chien-Tai Ren; Chi-Huey Wong; Chung-Yi Wu
Journal:  ACS Cent Sci       Date:  2021-12-21       Impact factor: 14.553

  10 in total

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