An approach towards efficient peptide synthesis in aqueous solution

Zbigniew J. Kamiński ,  Krzysztof Zając 

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

Abstract

An approach to efficient procedure of peptide synthesis in aqueous media is of grate importance since the safe disposal of organic solvents is an vital environmental issue, and even more essential, the indispensable ability of proteins, peptides, sugars and other potential drugs to preserve the correct conformation only in environment close to physiological conditions. Unfortunately, there are only few reports presenting resourceful results of peptide synthesis in aqueous solvents. To perform successful peptide synthesis or protein modification the coupling reagent must be water-soluble and maintain its reactivity in water. As one of the best suited to this particular goal were reported 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl- morpholinium chloride (DMT-MM) [1], In order to verify this literature reports the studies on versatility of triazine based coupling reagents [2] in aqueous media was been undertaken. We found that opposite to literature reports, synthesis of Z-Aaa-Bbb-OMe in methanol, gave set of amino acid methyl esters instead of expected dipeptides, but confirmed utility of ethanol and isopropanol as co-solvents. Furthermore, the yield of coupling strongly depended on the character of the base used in coupling procedure.

[1]. Hojo K, Maeda M, Tanakamaru N, Mochida K, Kawasaki K. Protein Pept Lett. 13, 189-192 (2006) and references cited therein.

[2]. Kamiński, Z.J.; Paneth, P.; Rudziński, J. J. Org. Chem. 63, 4248-4255 (1998).

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Presentation: Poster at VII Multidyscyplinarna Konferencja Nauki o Leku, by Zbigniew J. Kamiński
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-19 18:53
Revised:   2010-04-05 00:39
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