Peptide Synthesis by Oxidation-Reduction Condensation. I. Use of NPS-Peptides as Amino Component
- 1 April 1971
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 44 (4) , 1108-1111
- https://doi.org/10.1246/bcsj.44.1108
Abstract
Sulfenamides were found to react readily with soft nucleophiles in the presence of active hydrogen compounds. A new method for the synthesis of carboxamide from metal carboxylate, sulfenamide and tertiary phosphine was developed. The effects of metal component were examined. Copper(II) salts gave the best result. In a similar way, peptides were synthesized by the reaction of copper(II) salts of acylamino acid, or free acylamino acid in the presence of cupric chloride and triethylamine, with NPS-amino acid derivatives and triphenylphosphine. When organo-mercuric compounds such as dianisylmercury were used in place of cupric chloride and triethylamine in the above reaction, almost complete retention of configuration was observed by the Young test.Keywords
This publication has 7 references indexed in Scilit:
- A new method for peptide synthesis by oxidation-reduction condensationJournal of the American Chemical Society, 1968
- Effect of active ester components on racemization in the synthesis of peptides by the dicyclohexylcarbodiimide methodJournal of the American Chemical Society, 1967
- Synthesis of N-Hydroxysuccinimide Esters of Acyl Peptides by the Mixed Anhydride MethodJournal of the American Chemical Society, 1967
- Zur Synthese des Glucagons, X. Darstellung der Sequenz 22–29European Journal of Inorganic Chemistry, 1966
- New Methods in Peptide Synthesis. I. Tritylsulfenyl and o-Nitrophenylsulfenyl Groups as N-Protecting GroupsJournal of the American Chemical Society, 1963
- Zur Umsetzung des Bleitetraacetats mit Phenoläthern Mitteilung: Umsetzung mit ResorcindimethylätherArchiv der Pharmazie, 1960
- The Use of Phosphorous Acid Chlorides in Peptide Synthesis1Journal of the American Chemical Society, 1956