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Preparation of ?²-Homologous Amino Acids Bearing Polar Side Chains via a Collective Synthesis Strategy.

ABSTRACT: ?-Homologous amino acids (?hAAs) are a valuable class of building blocks for novel analogues of bioactive peptides. Thus, practical methods to synthesize enantiopure ?hAAs are desirable. We report the application of a collective synthesis strategy to prepare protected ?²-homologous amino acids with polar side chains. In this approach, a core structure is constructed via proline-catalyzed Mannich reaction and subsequently derivatized to furnish more than one protected ?²-homologous amino acid with a proteinogenic side chain.

SUBMITTER: Liu S

PROVIDER: S-EPMC7007826 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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Preparation of β2-Homologous Amino Acids Bearing Polar Side Chains via a Collective Synthesis Strategy.

Liu Shi S Gellman Samuel H SH

The Journal of organic chemistry 20200110 3

β-Homologous amino acids (βhAAs) are a valuable class of building blocks for novel analogues of bioactive peptides. Thus, practical methods to synthesize enantiopure βhAAs are desirable. We report the application of a collective synthesis strategy to prepare protected β2-homologous amino acids with polar side chains. In this approach, a core structure is constructed via proline-catalyzed Mannich reaction and subsequently derivatized to furnish more than one protected β2-hom ...[more]

PMID: 31920080

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