Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition
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- 作者：Marta I. Gutiérrez-Jiménez ; Carlos Aydillo ; Claudio D. Navo ; Alberto Avenoza ; Francisco Corzana ; Gonzalo Jiménez-Osés ; María M. Zurbano ; Jesús H. Busto ; Jesús M. Peregrina
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：June 17, 2016
- 年：2016
- 卷：18
- 期：12
- 页码：2796-2799
- 全文大小：367K
- 年卷期：0
- ISSN：1523-7052
文摘
A second generation of chiral bicyclic dehydroalanines easily accessible from serine has been developed. These scaffolds behaved as excellent S-Michael acceptors when tri-O-acetyl-2-acetamido-2-deoxy-1-thio-α-d-galactopyranose (abbreviated as GalNAc-α-SH) was used as a nucleophile. This addition proceeds with total chemo- and stereoselectivity, complete atom economy, quickly, and at room temperature, making it a true click reaction. The Michael adducts were easily transformed into S-(2-acetamido-2-deoxy-α-d-galactopyranosyl)-l- and -d-cysteines, which can be regarded as mimics of the Tn antigen derived from l-Ser (α-d-GalNAc-l-Ser) and d-Ser (α-d-GalNAc-d-Ser), respectively.