Issue 5, 2002
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Efficient stereoselective synthesis of peptidomimetics containing hydroxyethylamine dipeptide isosteres utilizing the aza-Payne rearrangement and O, N-acyl transfer reactions

Hirokazu Tamamura,*a   Tadakazu Hori,a   Akira Otakaa  and  Nobutaka Fujii*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan

Abstract

A novel methodology utilizing the aza-Payne rearrangement and O, N-intramolecular acyl transfer reactions for the synthesis of peptidomimetics containing hydroxyethylamine dipeptide isosteres (HDIs) is described. This methodology is useful for the stereoselective synthesis of HDI-containing pseudopeptides, and applicable to combinatorial chemistry using solid-phase techniques.

Graphical abstract: Efficient stereoselective synthesis of peptidomimetics containing hydroxyethylamine dipeptide isosteres utilizing the aza-Payne rearrangement and O, N-acyl transfer reactions

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Article information

DOI
https://doi.org/10.1039/B200324B
Article type
Communication
Submitted
08 Jan 2002
Accepted
24 Jan 2002
First published
01 Feb 2002

J. Chem. Soc., Perkin Trans. 1, 2002, 577-580

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Efficient stereoselective synthesis of peptidomimetics containing hydroxyethylamine dipeptide isosteres utilizing the aza-Payne rearrangement and O, N-acyl transfer reactions

H. Tamamura, T. Hori, A. Otaka and N. Fujii, J. Chem. Soc., Perkin Trans. 1, 2002, 577 DOI: 10.1039/B200324B

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