Peptide Synthesis in Aqueous Solution. I. Application of p-Dialkylsulfoniophenols as a Water-Soluble Coupling Reagent
- 1 July 1987
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 60 (7) , 2409-2418
- https://doi.org/10.1246/bcsj.60.2409
Abstract
(p-Hydroxyphenyl)dimethylsulfonium methyl sulfate(HODMSP·MeSO4−) was found to be an excellent coupling reagent having a water-soluble property and a high reactivity; it worked as satisfactory as usual active esters in regard to the reactivity, product purity, and racemization. The marked advantage of the HODMSP·MeSO4− active ester method was the fact that bifunctional residues such as Arg, Lys, Cys, and Tyr could be selectively acylated when the pH of the reaction mixture was controlled. The molluscan neuropeptide FMRFamide(Phe–Met–Arg–Phe–NH2) was synthesized by this new active ester method for an evaluation of this method to further applications involving peptide syntheses.Keywords
This publication has 25 references indexed in Scilit:
- The use of N-hydroxy-5-norbornene-2,3-dicarboximide acitive esters in peptide synthesis.CHEMICAL & PHARMACEUTICAL BULLETIN, 1974
- Synthesis of Bradykinyl-Val-Ala-Pro-Ala-Ser-OH and Its Biological PropertiesCHEMICAL & PHARMACEUTICAL BULLETIN, 1973
- The Removal of Copper from the Copper Complex of ω-Acylamino Acid with EDTABulletin of the Chemical Society of Japan, 1965
- Zur Synthese des Glucagons, I. Darstellung der Sequenz 1–4European Journal of Inorganic Chemistry, 1964
- New Methods in Peptide Synthesis. I. Tritylsulfenyl and o-Nitrophenylsulfenyl Groups as N-Protecting GroupsJournal of the American Chemical Society, 1963
- A Method of Synthesis of Long Peptide Chains Using a Synthesis of Oxytocin as an ExampleJournal of the American Chemical Society, 1959
- Effects of Dimethylsulfonio and Trimethylammonio Groups on the Dissociation of Substituted PhenolsJournal of the American Chemical Society, 1958
- Carbobenzoxy Derivatives of Histidine, Imidazole and Benzimidazole1Journal of the American Chemical Society, 1957
- Conjugative Effects in Divalent Sulfur Groupings1Journal of the American Chemical Society, 1956
- Conjugative Effects of Dimethylsulfonio [(CH3)2S+] and Trimethylammonio [(CH3)3N+] Groups1,2Journal of the American Chemical Society, 1956