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

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Resumo

A new efficient synthetic approach for the preparation of Nα-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.

Sobre autores

V. Azev

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Autor responsável pela correspondência
Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

L. Baidakova

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

A. Chulin

Branch of Shemyakin and Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, prosp. Nauki 6

A. Tuzikov

Shemyakin-Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 117997, Moscow, ul. Miklukho-Maklaya 16/10

P. Kislitsyn

CHEMRAR Group

Email: viatcheslav.azev@bibch.ru
Russia, 141401, Khimki, ul. Rabochaya 2a-1

M. Molchanov

Institute for Theoretical and Experimental Biophysics, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 142290, Pushchino, ul. Institutskaya 3

A. Miroshnikov

Shemyakin-Ovchinnikov Bioorganic Chemistry Institute, RAS

Email: viatcheslav.azev@bibch.ru
Russia, 117997, Moscow, ul. Miklukho-Maklaya 16/10

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Declaração de direitos autorais © В.Н. Азев, Л.К. Байдакова, А.Н. Чулин, А.Б. Тузиков, П.Г. Кислицин, М.В. Молчанов, А.И. Мирошников, 2023