Studies on peptides. LXXXI. Application of a new arginine derivative, NG-mesitylene-2-sulfonylarginine, to the synthesis of substance P and neurotensin

International Journal of Peptide and Protein Research
H YajimaY Akazawa

Abstract

A new devised arginine derivative, NG-mesitylene-2-sulfonylarginine, Arg(Mts), was employed for the synthesis of hypothalamic substance P and neurotensin. The former was obtained in 74% yield by treatment of the protected undecapeptide amide, Z - Arg(Mts) - Pro - Lys(Z) - Pro - Gln - Gln - Phe - Phe - Gly - Leu - Met(O)-NH2, with methanesulfonic acid in the presence of anisole followed by reduction of the sulfoxide with 2-mercaptoethanol. The latter was obtained in 54% yield by the similar treatment of the protected tridecapeptide ester, Z - Pyr - Leu - Tyr - Glu(OBzl) - Asn - Lys(Z) - Pro - Arg(Mts) - Arg(Mts) - Pro - Tyr - Ile - Leu - OBzl, with methanesulfonic acid. As scavenger, a mixture of anisole-thioanisole-o-cresol (1:1:1, by vol.) was employed to suppress the side reaction, O-mesitylene-2-sulfonation of the Tyr residue.

References

Apr 1, 1978·Chemical & Pharmaceutical Bulletin·H YajimaY Nakata
Nov 1, 1976·Proceedings of the National Academy of Sciences of the United States of America·K FolkersC Y Bowers
Aug 1, 1974·Journal of Medicinal Chemistry·G H FisherC Y Bowers
Jul 21, 1971·Nature: New Biology·M M ChangH D Niall
Jul 21, 1971·Nature: New Biology·G W TregearM M Chang

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Citations

Oct 1, 1985·International Journal of Peptide and Protein Research·H YajimaK Akaji
Nov 1, 1990·International Journal of Peptide and Protein Research·H NakamuraH Aoyagi
Apr 15, 2009·Chemical Reviews·Albert Isidro-LlobetFernando Albericio
Dec 10, 1998·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·K YanoY Imanishi
Oct 1, 1986·Japanese Journal of Pharmacology·H NakamutaR C Orlowski

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