Synthesis of chiral triazine coupling reagents based on esters of N-alkylproline and their application in the enantioselective incorporation D or L amino acid residue directly from racemic substrate

Katarzyna M. Kasperowicz-Frankowska ,  Michał Dziemidkiewicz ,  Anna Gzik ,  Beata Kolesińska ,  Zbigniew J. Kamiński 

Technical University of Łódź, Institute of Organic Chemistry (PŁ), Żeromskiego 116, Łódź 90-924, Poland

Abstract

The concept of traceless enantioselective coupling reagents is based on chiral 1,3,5-triazine derivatives with the chiral fragment departing after the activation of a carboxylic component. According to this concept, such reagents are prepared by temporary attachment of the chiral fragment to a classical peptide-bond-forming agent. Thus, after selection of the enantiomer at the activation stage and departure of the chiral component, the activated intermediate is converted to a well-known form of a conventional acylating species [1]. It has been shown that configuration and enantiomeric enrichment once established remain intact and independent on the structure of acylated counterpart. Furthermore, as anticipated, parameters like configuration, optical purity of the product, and the efficiency of coupling were predictable on the basis of a single experiment of the model reaction. Application of chiral N-triazinylamonium salts derived from alkaloids (brucine, strychnine, quinine) yielded peptides within up to 99% enantiomeric purity from racemic substrate, with expected configuration, obtained in high yield under coupling procedure typical for other triazine coupling reagents [2]. Until now, the main limitation in the broad application of the traceless coupling reagents are toxicity of the alkaloids and limited access to both enantiomeric forms of the chiral component of coupling reagent.

Thus, to open access to the representative collection of non-toxic chiral coupling reagents readily available in both enantiomeric forms the systematic studies were undertaken to develop versatile procedures for transformation of proline readily available in d and l form into versatile chiral component. Herein are presented results of application of N-methyl or N-allilproline esters for the synthesis of chiral tracelles coupling reagents and their application in the synthesis of peptide directly from racemic amino acids.

Acknowledgement:

This study was supported by the Ministry of Science and High Education under the Reserch Project from National Science Center: project number: 2012/07/N/ST5/01883

References:

[1] B. Kolesińska, Z.J. Kamiński, Org. Lett., 11, 765-768 (2009).

[2] (a) B. Kolesińska, K. Kasperowicz, M. Sochacki, A. Mazur, S. Jankowski, Z.J. Kamiński. Tetrahedron Lett. 51, 20–22 (2010); (b) Kamiński, Z.J.; Kolesińska, B.Patent EPO 09001796,3-1211, priority PL/04.02.08/ PLA 384377608. 

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Presentation: Poster at IX Multidyscyplinarna Konferencja Nauki o Leku, by Katarzyna M. Kasperowicz-Frankowska
See On-line Journal of IX Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2014-03-15 12:59
Revised:   2014-05-02 10:58
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