α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base

A general protocol for the synthesis of α,β-dehydroamino acids and their peptides was developed. Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes. The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and fur...

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Published inPrecision Chemistry Vol. 2; no. 1; pp. 14 - 20
Main Authors Sawamura, Jun, Ieiri, Daikan, Yazaki, Ryo, Ohshima, Takashi
Format Journal Article
LanguageEnglish
Published United States University of Science and Technology of China and American Chemical Society 22.01.2024
American Chemical Society
Subjects
proline
transimination
α,β-dehydroamino acid
peptide
aldol condensation
glycine Schiff base
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Summary:A general protocol for the synthesis of α,β-dehydroamino acids and their peptides was developed. Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes. The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-free α,β-dehydroamino esters. Peptide elongation of both the C- and N-terminals highlighted the usefulness of our present protocol.
Bibliography:ObjectType-Article-1
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ISSN:2771-9316
2771-9316
DOI:10.1021/prechem.3c00048