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Literature DB >> 21423783

Synthesis of Human Cancer Associated Globo-H (MBr1) Glycosylamino Acid: Some Mechanistic and Conformational Reinvestigations.

Jianglong Zhu¹, Qian Wan, Guangbin Yang, Ouathek Ouerfelli, Samuel J Danishefsky.

Abstract

The synthesis of an extended globo-H (MBr1 antigen) in the form of a glycosylamino acid is reported. By careful NMR analysis, we found an interesting conformational "flip" on the E ring of some synthetic intermediates. An explanation offered for the successful [3+3] coupling of ABC acceptor 11 and DEF donor 10 possessing a C4 free hydroxyl to produce β-galactoside in azaglycosidations is reinforced.

Entities: CellLine Chemical Disease Gene Species

Year: 2009 PMID： 21423783 PMCID： PMC3059307 DOI： 10.3987/COM-08-S(D)82

Source DB: PubMed Journal: Heterocycles ISSN： 0385-5414 Impact factor: 0.831

14 in total

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Authors:
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Review 2. Augmenting the immunogenicity of carbohydrate tumor antigens.

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4. A highly convergent chemical synthesis of conformational epitopes of rhamnogalacturonan II.

Authors: Yu Rao; Geert-Jan Boons
Journal: Angew Chem Int Ed Engl Date: 2007 Impact factor: 15.336

5. Characterization of a glycosphingolipid antigen defined by the monoclonal antibody MBr1 expressed in normal and neoplastic epithelial cells of human mammary gland.

Authors: E G Bremer; S B Levery; S Sonnino; R Ghidoni; S Canevari; R Kannagi; S Hakomori
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6. Pursuit of optimal carbohydrate-based anticancer vaccines: preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewis(y) antigens.

Authors: J R Allen; C R Harris; S J Danishefsky
Journal: J Am Chem Soc Date: 2001-03-07 Impact factor: 15.419

7. 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

8. 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

9. 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

3. 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

3 in total