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Synthesis of a new symmetric carbonate with leaving group

A. -E. SEGNEANU1, M. MILEA2, I. GROZESCU1,*

Affiliation

  1. National Institute Research Development for Electrochemistry and Condensed Matter, 144 Dr. A. P. Podeanu Street, 300569 Timisoara, Romania
  2. Polytechnica University of Timisoara, 1 P-ta Victoriei Street, 300006, Timisoara, Romania

Abstract

The study of the reactivity of organic reactive carbonates with leaving groups (succinimidyl, phthtalimidyl and norbornenyl) towards oxygen and nitrogen nucleophiles proved to be useful due to the applicability of the resulting compounds in avant-garde fields of chemistry, such as biochemistry and the pharmaceutical industry. This study has been heavily focused on developing new, cleaner, chemical processes using an original method. The goal of this paper is to prepare a new symmetrical reactive carbonate with leaving group by an original method, aimed at reducing chemical residues with a negative impact on the environment and human health. In peptide synthesis, reactive organic carbonates are used especially for the protection of amino groups, by converting it into a carbamate-type derivative through an alkoxycarbonylation reaction, and for the activation of carboxyl groups by converting it into a reactive ester. For the protection of the amino function in amino acids, alkoxycarbonyl-type (carbamate) groups are preferred, which minimize the racemization of optically active centers. In modern peptide synthesis, at the international level, the applications of phthtalimidyl organic carbonates are related to the activation of carboxyl groups in amino acids and peptides. The process of obtaining symmetrical carbonate with leaving group is the starting point for obtaining new amino-protecting groups with special importance in the synthesis of peptides..

Keywords

Alkoxycarbonyl-type (carbamate) groups, Leaving group, Norbornenyl, racemisation.

Citation

A. -E. SEGNEANU, M. MILEA, I. GROZESCU, Synthesis of a new symmetric carbonate with leaving group, Optoelectronics and Advanced Materials - Rapid Communications, 6, 1-2, January-February 2012, pp.197-199 (2012).

Submitted at: Jan. 14, 2011

Accepted at: Feb. 20, 2012