S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

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• 作者：Carlos Aydillo ; Ismael Compa?ón ; Alberto Avenoza ; Jesús H. Busto ; Francisco Corzana ; Jesús M. Peregrina ; María M. Zurbano
• 刊名：Journal of the American Chemical Society
• 出版年：2014
• 出版时间：January 15, 2014
• 年：2014
• 卷：136
• 期：2
• 页码：789-800
• 全文大小：628K
• ISSN：1520-5126

文摘

Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(尾-d-glucopyranosyl)-d-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-伪-d-galactopyranosyl)-l-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.