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

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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.

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

Document Type: Research Article


Affiliations: Faculty of Pharmaceutical Sciences, Kobe Gakuin University, Ikawadani-cho, Nishiku, Kobe 651-2180, Japan.

Publication date: 2006-02-01

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  • Protein & Peptide Letters publishes short papers in all important aspects of protein and peptide research, including structural studies, recombinant expression, function, synthesis, enzymology, immunology, molecular modeling, drug design etc. Manuscripts must have a significant element of novelty, timeliness and urgency that merit rapid publication. Reports of crystallisation, and preliminary structure determinations of biologically important proteins are acceptable. Purely theoretical papers are also acceptable provided they provide new insight into the principles of protein/peptide structure and function.
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