Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives.

Abstract

A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, D-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected D- or L-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (∼100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

• Authors: Ahmad Ali Shaik, Sharmeen Nishat, Peter R Andreana
• Journal: Organic letters (Org Lett) Vol. 17 Issue 11 Pg. 2582-5 (Jun 05 2015) ISSN: 1523-7052 [Electronic] United States
• PMID: 25988425 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)

Chemical References

• Antigens, Tumor-Associated, Carbohydrate
• Biological Products
• Hydrazines
• Tn antigen

Topics

• Antigens, Tumor-Associated, Carbohydrate (chemistry)
• Biological Products (chemical synthesis, chemistry)
• Glycosylation
• Hydrazines (chemical synthesis, chemistry)
• Molecular Structure
• Stereoisomerism