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Title

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

AuthorsFernández, Fernando; Fernández, Alberto G.; Balo, Rosalino; Sánchez-Pedregal, Víctor M.; Royo, Miriam CSIC ORCID ; Soengas, Raquel G; Estévez, Ramón J.; Estévez, Juan C.
Keywordsβ-amino acid
Issue Date18-Jan-2022
PublisherAmerican Chemical Society
CitationACS Omega 7 (2): 2002–2014 (2022)
AbstractA stereoselective synthesis of polyhydroxylated cyclopentane β-amino acids from hexoses is reported. The reaction sequence comprises, as key steps, ring-closing metathesis of a polysubstituted diene intermediate followed by the stereoselective aza-Michael functionalization of the resulting cyclopent-1-ene-1-carboxylic acid ester. Examples of synthesis of polysubstituted 2-aminocyclopentanecarboxylic acid derivatives starting from protected d-mannose and d-galactose are presented. A general protocol for the incorporation of these highly functionalized alicyclic β-amino acids into peptides is also reported.
URIhttp://hdl.handle.net/10261/259358
DOI10.1021/acsomega.1c05468
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