Regiospecific Preparation of a Suitably Protected β-Branched Aspartic Acid Dipeptide

V. N. Azev; Азев В. Н.; L. K. Baidakova; Байдакова Л. К.; A. N. Chulin; Чулин А. Н.; A. B. Tuzikov; Тузиков А. Б.; P. G. Kislitsyn; Кислицин П. Г.; M. V. Molchanov; Молчанов М. В.; A. I. Miroshnikov; Мирошников А. И.

doi:10.31857/S0132342323040279

Regiospecific Preparation of a Suitably Protected β-Branched Aspartic Acid Dipeptide

Authors: Azev V.N.¹, Baidakova L.K.¹, Chulin A.N.¹, Tuzikov A.B.², Kislitsyn P.G.³, Molchanov M.V.⁴, Miroshnikov A.I.²
Affiliations:
1. Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS
2. Shemyakin-Ovchinnikov Bioorganic Chemistry Institute, RAS
3. CHEMRAR Group
4. Institute for Theoretical and Experimental Biophysics, RAS
Issue: Vol 49, No 4 (2023)
Pages: 411-421
Section: Articles
URL: https://rjmseer.com/0132-3423/article/view/670589
DOI: https://doi.org/10.31857/S0132342323040279
EDN: https://elibrary.ru/ODAVUU
ID: 670589

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Abstract

A new efficient synthetic approach for the preparation of N_α-protected β-L-aspartyl-L-aspartic acid dipeptide was elaborated. The distinctive features of the developed approach include utilization of readily available starting materials (Cbz-asparagine and dimethyl aspartate), aspartimide formation suppression employing electrostatic effect in a final deprotection step and an employment of a novel reagent (NaNO₂/aqueous trifluoroacetic acid) for transformation of protected asparagine derivative into the corresponding aspartic acid. The developed method allowes preparation of aspartic acid derivatives that find application in carbohydrate polivalent interaction studies as well as in preparation of microbicidal dendrimeric constructs.

Keywords

aspartimide formation suppression, asparagine side-chain nitrosylation, orthogonal protecting group

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