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

Organic Letters
Ahmad Ali ShaikPeter R Andreana

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.

References

Jun 15, 1984·Science·G F Springer
Aug 1, 1997·Journal of Molecular Medicine : Official Organ of the Gesellschaft Deutscher Naturforscher Und Ärzte·G F Springer
Mar 20, 2003·Bioconjugate Chemistry·Line Bourel-BonnetOleg Melnyk
Dec 9, 2003·Chembiochem : a European Journal of Chemical Biology·Reshma AutarRoland J Pieters
Mar 6, 2004·Cancer Metastasis Reviews·James C Byrd, Robert S Bresalier
Jul 8, 2008·Chemistry : a European Journal·Alberto Fernández-TejadaAlberto Avenoza
Apr 15, 2009·Chemical Reviews·Albert Isidro-LlobetFernando Albericio
Jun 6, 2009·The Journal of Organic Chemistry·Jasper DinkelaarGijsbert A van der Marel
Jun 26, 2009·Journal of the American Chemical Society·Ravindra A De SilvaPeter R Andreana
Jan 25, 2011·Angewandte Chemie·Tongzhong JuRichard D Cummings
Apr 1, 2011·Chemical Communications : Chem Comm·Francisco CorzanaJesús M Peregrina
Dec 16, 2011·Proceedings of the National Academy of Sciences of the United States of America·Vani LakshminarayananGeert-Jan Boons
Feb 3, 2012·Cancer Immunology, Immunotherapy : CII·Ravindra A De SilvaPeter R Andreana
Mar 20, 2013·ACS Chemical Biology·Zhaojun YinXuefei Huang
Jul 4, 2013·Journal of the American Chemical Society·Hong-Yang ChuangChi-Huey Wong
Aug 16, 2013·Journal of the American Chemical Society·Rebecca M Wilson, Samuel J Danishefsky

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Citations

Nov 3, 2016·Journal of the American Chemical Society·Mengchao ShiPeter R Andreana
Mar 8, 2018·Medicinal Research Reviews·Meng-Man WeiXin-Shan Ye

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