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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 β<sup>2</sup>-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 β<sup>2</sup>-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 β<sup>2</sup>-hom  ...[more]

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