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Enantioselective Synthesis of D-?-Amino Amides from Aliphatic Aldehydes.

ABSTRACT: Peptides consisting of D-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of D-amino amides most often involves approaches based on enzymatic resolution or fractional recrystallization of their diastereomeric amine salts, techniques that produce an equal amount of the L-amino acid. Enantioselective synthesis, however, promises selective and general access to a specific ?-amino amide, and may enable efficient peptide synthesis regardless of the availability of the corresponding ?-amino acid. This report describes the use of a cinchona alkaloid-catalyzed aza-Henry reaction using bromonitromethane, and the integration of its product with Umpolung Amide Synthesis. The result is a straightforward 3-step protocol beginning from aliphatic aldehydes that provides homologated peptides bearing an aliphatic side chain at the resulting D-?-amino amide.

SUBMITTER: Schwieter KE

PROVIDER: S-EPMC4378585 | biostudies-literature | 2015

REPOSITORIES: biostudies-literature

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Enantioselective Synthesis of D-α-Amino Amides from Aliphatic Aldehydes.

Schwieter Kenneth E KE Johnston Jeffrey N JN

Chemical science 20150101 4

Peptides consisting of D-amino amides are highly represented among both biologically active natural products and non-natural small molecules used in therapeutic development. Chemical synthesis of D-amino amides most often involves approaches based on enzymatic resolution or fractional recrystallization of their diastereomeric amine salts, techniques that produce an equal amount of the L-amino acid. Enantioselective synthesis, however, promises selective and general access to a specific α-amino a ...[more]

PMID: 25838883

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