vestichИзвестия Национальной академии наук Беларуси. Серия химических наукProceedings of the National Academy of Sciences of Belarus, Chemical Series1561-83312524-2342The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"vestich-289Research ArticleОРГАНИЧЕСКАЯ ХИМИЯORGANIC CHEMISTRYТРИФТОРАЦЕТИЛЬНАЯ АМИНОЗАЩИТНАЯ ГРУППА В СИНТЕЗЕ L-АЛАНИЛ- L-ГЛУТАМИНОВОЙ КИСЛОТЫ И L-α,γ-ГЛУТАМИЛ-БИС(L-АЛАНИНА)TRIFLUOROACETYL AMINO-PROTECTIVE GROUP IN SYNTHESIS OF L-ALANYLL-GLUTAMIC ACID AND L-α,γ-GLUTAMYL-BIS(L-ALANINE)ПоповаЛ. А.PopovaL. A.

ст. науч. сотрудник

ул. Сурганова, 13, 220072

Senior Researcher

13, Surganov Str., 220072

ЗубрейчукЗ. П.ZubreichukZ. P.

ст. науч. сотрудник

ул. Сурганова, 13, 220072

Senior Researcher

13, Surganov Str., 220072

КнижниковВ. А.KnizhnikovV. A.

д-р хим. наук, зав. лаб.

ул. Сурганова, 13, 220072

D. Sc. (Chemistry), Head of the Laboratory

13, Surganov Str., 220072

knizh@ifoch.bas-net.byИнститут физико-органической химии НАН Беларуси, МинскInstitute of Physical Organic Chemistry of the National Academy of Sciences of Belarus, Minsk201714122017045561Copyright © Попова Л.А., Зубрейчук З.П., Книжников В.А., 20172017Попова Л.А., Зубрейчук З.П., Книжников В.А.Popova L.A., Zubreichuk Z.P., Knizhnikov V.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://vestichem.belnauka.by/jour/article/view/289

Конденсацией N-трифторацетил-L-аланина с диметиловым эфиром L-глутаминовой кислоты и N-трифторацетил-L-глутаминовой кислоты с метиловым эфиром L-аланина под действием дициклогексилкарбодиимида получены диметиловый эфир N-трифторацетил-L-аланил-L-глутаминовой кислоты и N-трифторацетил-Lα,γ-глутамил-бис(метокси-L-аланин) соответственно. Удаление защитных групп в синтезированных соединениях под действием гидроксида натрия и последующее подкисление реакционных смесей привели к образованию L-аланил-L-глутаминовой кислоты и L-α,γ-глутамил-бис(L-аланина). N-Трифторацетил-L-аланин и N-трифторацетил-L-глутаминовая кислота получены из натриевых солей L-аланина и L-глутаминовой кислоты с использованием в качестве ацилирующего агента этилтрифторацетата. 

N-Trifluoroacetyl-L-alanyl-L-glutamic acid dimethyl ester and N-trifluoroacetyl-L-α,γ-glutamyl-bis(methoxy-L-alanine) were obtained by condensation of N-trifluoroacetyl-L-alanine with L-glutamic acid dimethyl ester and N-trifluoroacetyl-L-glutamic acid with L-alanine methyl ester, respectively. Removal of protecting groups by sodium hydroxide in the compounds obtained and subsequent acidification of the reaction mixtures led to the formation of L-alanylL-glutamic acid and L-α,γ-glutamyl-bis(L-alanine). N-Trifluoroacetyl-L-alanine and N-trifluoroacetyl-L-glutamic acid were obtained from L-alanine and L-glutamic acid sodium salts using ethyl trifluoroacetate as an acetylating agent. 

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The authors declare that there are no conflicts of interest present.