Synthesis of Conjugates of N-(Purin-6-yl)-6-Aminohexanoic Acid with 4-Amino-1-Aryl-5-Oxoprolines

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Abstract

(2S,4S)-4-Amino-1-aryl-5-oxoprolines were synthesized by nucleophilic substitution of the bromine atom in dimethyl (2S,4RS)-4-bromo-N-phthaloylglutamate under the action of difluorosubstituted anilines followed by isolation of (2S,4S)-diastereomers and removal of protecting groups; subsequent coupling of their methyl esters with N-(purin-6-yl)-6-aminohexanoic acid and saponification of ester groups led to the formation of target conjugates. The saponification of ester groups was accompanied by minor epimerization.

About the authors

A. Yu. Vigorov

Postovsky Institute of Organic Synthesis, UB RAS

Email: vigorov@ios.uran.ru
ORCID iD: 0000-0003-4619-4341
Yekaterinburg, Russia

O. A. Vozdvizhenskaya

Postovsky Institute of Organic Synthesis, UB RAS

ORCID iD: 0000-0001-8349-6061
Yekaterinburg, Russia

A. A. Tumashov

Postovsky Institute of Organic Synthesis, UB RAS

ORCID iD: 0000-0001-9383-2006
Yekaterinburg, Russia

T. V. Matveeva

Postovsky Institute of Organic Synthesis, UB RAS

Yekaterinburg, Russia

I. N. Ganebnykh

Postovsky Institute of Organic Synthesis, UB RAS

ORCID iD: 0000-0002-8487-8448
Yekaterinburg, Russia

G. L. Levit

Postovsky Institute of Organic Synthesis, UB RAS

ORCID iD: 0000-0002-0964-9311
Yekaterinburg, Russia

V. P. Krasnov

Postovsky Institute of Organic Synthesis, UB RAS

ORCID iD: 0000-0003-1411-6218
Yekaterinburg, Russia

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