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J Org Chem. 2017 Feb 3;82(3):1833-1841. doi: 10.1021/acs.joc.6b02718. Epub 2017 Jan 24.

Access to Enantiopure α-Hydrazino Acids for N-Amino Peptide Synthesis.

Author information

1
Department of Chemistry, University of South Florida , Tampa, Florida 33620, United States.

Abstract

Backbone N-methylation of α-peptides has been widely employed to enhance the bioavailability and bioactivity of parent sequences. Heteroatomic peptide amide substituents have received less attention due, in part, to the lack of practical synthetic strategies. Here, we report the synthesis of α-hydrazino acids derived from 19 out of the 20 canonical proteinogenic amino acids and demonstrate their use in the solid-phase synthesis of N-amino peptide derivatives.

PMID:
28075135
DOI:
10.1021/acs.joc.6b02718

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