Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition | Zendy

Marta I. GutiérrezJiménez | Zendy; Carlos Aydillo | Zendy; Claudio D. Navo | Zendy; Alberto Avenoza | Zendy; Francisco Corzana | Zendy; Gonzalo JiménezOsés | Zendy; Marı́a M. Zurbano | Zendy; Jesús H. Busto | Zendy; Jesús M. Peregrina | Zendy

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Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition

Author(s) -

Marta I. GutiérrezJiménez,

Carlos Aydillo,

Claudio D. Navo,

Alberto Avenoza,

Francisco Corzana,

Gonzalo JiménezOsés,

Marı́a M. Zurbano,

Jesús H. Busto,

Jesús M. Peregrina

Publication year - 2016

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b00840

Subject(s) - chemistry , stereoselectivity , michael reaction , bifunctional , nucleophile , adduct , stereochemistry , serine , bicyclic molecule , thio , catalysis , organic chemistry , enzyme

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.

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