Sulfonates of N-Triazinylammonium Salts as Highly Efficient and Environmentally Friendly Triazine-Based Coupling Reagents

Beata Kolesińska ,  Justyna Frączyk ,  Kamil Rożniakowski ,  Zbigniew J. Kamiński 

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

Abstract

Peptide synthesis depends on the proper combination of protecting groups and the right choice of the coupling method. An optimal coupling reagent should be valid for a wide variety of peptide sequences. It should be soluble and stable in the solvents used for peptide synthesis, efficient in terms of yield, minimize the racemization.

General method of preparation of stable N-triazinylammonium salts opened access to family of N-triazinylammonium sulfonates [1]. Sulfonates of N-triazinylammonium salts consist the family of inexpensive and environmentally friendly Triazine-Based Coupling Reagents. A broad variety of N-triazinylammonium sulfonates can be obtained by treatment of 2-chloro-4,6-disubstituted1,3,5-triazines with sulfonates of tertiary amines.

sulfoniany.jpg

Up to now, we demonstrated that they can be useful for activation of carboxylic components, with activation rate depending on the structure of the tertiary amine component and sulfonic acid counterion. Participation of triazine “superactive ester”, as fundamental intermediate in condensation step, has been proved in model experiments [2]. Herein, we present the studies on screening of family of N-trizainylammonium sulfonates in peptide bond formation in solution and solid phase synthesis. The efficacy of the family of new N-triazinylammonium sulfonates as a coupling reagent in solution was examined using two models systems: Z-Aib-OH + H-Aib-OMe and Z-Leu-Phe-OH + H-Ile-OBut. The effectiveness of the family of N-triazinylammonium sulfonates in solid-phase mode was demonstrated in the synthesis of ACP(65-74) (ACP: H-Val-Gln-Ala-Ala-Ile-Asp-Tyr-Ile-Asn-Gly-OH), which is a good example of difficult peptide sequence, because of the development of internal secondary structures.

Acknowledgement: This work was supported by the Grant donated by the Technical University of Łódź.

[1] Kamiński, Z. J.; Kolesińska, B.; Kolesińska, J.; Jastrząbek, K. Eur. Pat. Appl. EP1586566 A1 from 19.10.2005, CA 143: 387385 (2006).
[2] Kolesińska, B.; Frączyk, J.; Papini, A.M.; Kamiński, Z.J., Chemistry Today (Chimica Oggi) 2007, 25(1), 26-29.

Legal notice
  • Legal notice:

    Copyright (c) Pielaszek Research, all rights reserved.
    The above materials, including auxiliary resources, are subject to Publisher's copyright and the Author(s) intellectual rights. Without limiting Author(s) rights under respective Copyright Transfer Agreement, no part of the above documents may be reproduced without the express written permission of Pielaszek Research, the Publisher. Express permission from the Author(s) is required to use the above materials for academic purposes, such as lectures or scientific presentations.
    In every case, proper references including Author(s) name(s) and URL of this webpage: http://science24.com/paper/14780 must be provided.

 

Related papers
  1. Preliminary studies on application of library of artificial receptors for differentiation of metabolites in urine of healthy and cancer mice
  2. 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
  3. 1,3-Oxazolidin-5-ones as chiral components in the synthesis of traceless enantioselective reagents
  4. Attempts to application of libraries of N-lipidated amino acids and peptides immobilized   on cellulose as a stereosectors
  5. An Approach for Application of Synthetic Peptides as Markers of Atherosclerotic Diseases
  6. Synthesis and Antimicrobial Activity of P-Tria- zinylphosphonium Salts
  7. Traceless chiral coupling reagent. A new concept for synthesis of optically active products from racemic carboxylic acids.
  8. An approach towards efficient peptide synthesis in aqueous solution
  9. Synthesis and application of library of artificial receptors immobilized on cellulose support
  10. Design and synthesis of libraries of artificial enzymes
  11. Rate of Binding of Host Molecules to Artificial Receptors Formed by Self-Organisation of Lipidated Oligopeptides
  12. Synthesis of Building Blocks Containing Glycosyl Moieties by Using Triazinylammonium Sulfonates
  13. Transformation of Tertiary Amines into N-Triazinylated Analogues by Treatment with Chloro-1,3,5-Triazines
  14. The New Analogues of Nitrogen Mustard With One, Two or Three 2-Chloroethylamino Fragments. Reactions with Nucleophiles
  15. Synthesis and Screening of the Library of the Supramolecular Structures Formed by N-Lipidated Oligopeptides for Selection of Host Active as Artificial Esterase
  16. AN APPLICATION OF THE ARRAY OF LIPIDATED OLIGOPEPTIDES RESEMBLING ARTIFICIAL RECEPTORS FOR MOLECULAR RECOGNITION. THE STUDIES ON THE LIPOPHLILICITY OF SOME PIPERAZINES
  17. SYNTHESIS AND SEROLOGICAL INTERACTIONS OF H.PYLORI UREASE FRAGMENT 321-339 IMMOBILIZED ON THE CELLULOSE SUPPORT
  18. AN APPLICATION OF CHIRAL COUPLING REAGENTS FOR ENANTIOSELECTIVE ACTIVATION OF RACEMIC N-BENZOYL- 2-HYDROXYMETHYL-2-AMINO ACIDS
  19. THE NEW WATER SOLUBLE SALTS, PRONE TO SPONTANEOUS DECOMPOSITION WITH FORMATION OF 2-CHLOROETHYLAMINO MOIETY (NITROGEN MUSTARD DERIVATIVES)

Presentation: Poster at VI Multidyscyplinarna Konferencja Nauki o Leku, by Justyna Frączyk
See On-line Journal of VI Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2008-03-15 09:09
Revised:   2009-06-07 00:48
Google
 
Web science24.com
© 1998-2022 pielaszek research, all rights reserved Powered by the Conference Engine