Solid Phase Peptide Synthesis in Water VI: Evaluation of Water-Soluble Coupling Reagents for Solid Phase Peptide Synthesis in Aqueous Media

Title: Solid Phase Peptide Synthesis in Water VI: Evaluation of Water-Soluble Coupling Reagents for Solid Phase Peptide Synthesis in Aqueous Media

Volume: 13 Issue: 2

Author(s): Keiko Hojo, Mitsuko Maeda, Naoko Tanakamaru, Kayo Mochida and Koichi Kawasaki

Affiliation:

Keywords: 2-(4-Sulfophenylsulfonyl)ethoxycarbonyl group, Solid phase peptide synthesis in water, 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)

Abstract: Solid phase peptide synthesis requires large amounts of organic solvents, the safe disposal of which is an important environmental issue. Peptide synthesis, if performed in water and using less or nontoxic reagents, circumvents the disposal problem. Our ultimate aim is to develop an "environment-friendly" solid phase peptide synthesis (SPPS) methodology. Previously, we showed that SPPS in water is feasible. To perform SPPS in water, the coupling reagent must be water-soluble and maintain its reactivity in water. For this report, we tested the efficacy of the water-soluble coupling reagents, 2-(5-norbornene-2,3-dicarboximido)-1,1,3,3-tetramethyluronium tetrafluoroborate (TNTU) and 4-(4,6- dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM), towards SPPS in water. We successfully synthesized Leu-enkephalin amide on A solid support suspended in aqueous 50% EtOH using DMT-MM and 2-(4- sulfophenylsulfonyl)ethoxycarbonylamino acids.

Cite this article as:

Hojo Keiko, Maeda Mitsuko, Tanakamaru Naoko, Mochida Kayo and Kawasaki Koichi, Solid Phase Peptide Synthesis in Water VI: Evaluation of Water-Soluble Coupling Reagents for Solid Phase Peptide Synthesis in Aqueous Media, Protein & Peptide Letters 2006; 13 (2) . https://dx.doi.org/10.2174/092986606775101607

DOI https://dx.doi.org/10.2174/092986606775101607	Print ISSN 0929-8665
Publisher Name Bentham Science Publisher	Online ISSN 1875-5305