Polyhydroxylated cyclopentane β-amino acids derived from D-mannose and D-galactose: synthesis and protocol for incorporation into peptides

Abstract

A stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported.The reaction sequence comprises as key steps a Ring Closing Metathesis of a polysubstituted diene intermediate, followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected D-mannose and D-glucose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported.

Polyhydroxylated Cyclopentane β-Amino Acids Derived from d-Mannose and d-Galactose: Synthesis and Protocol for Incorporation into Peptides

“…In one case, we observed an unwanted elimination reaction when trying to couple these β-amino acids into peptides as already described in a previous work . Finally, we devised an alternative and more general procedure for the successful incorporation of this type of amino acids into peptides …”