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Studies on Arginine Peptides. II. Synthesis of L-Arginyl-L-arginine and other N-Terminal Arginine Dipeptides

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Studies on Arginine Peptides. II. Synthesis of L-Arginyl-L-arginine and other N-Terminal Arginine Dipeptides
Zervas, L. Otani, T.T. Winitz, M. Greenstein, J.P.
scientific_publication_article
Επιστημονική δημοσίευση - Άρθρο Περιοδικού (EL)
Scientific publication - Journal Article (EN)
1959
Dicarbobenzoxy-L-arginine and tricarbobenzoxy-L-arginine have been utilized for the preparation of a variety of dipeptides containing an N-terniinal arginine residue. The former compound, either as its acid chloridehydrochloride derivative or under the condensing action of dicyclohexylcarbodiimide, was coupled with diethyl L-glutamate and the condensation product subsequently converted to the corresponding free peptide via successive saponification and catalytic hydrogenolysis; the formation of Nα,Nπ-dicarbobenzoxyanhydro-L-arginine accompanied the coupling reaction, an occurrence presumably attributable to the fact that the basicity of the guanido moiety of Nα,Nπdiacylated arginines is not completely masked. No analogous evidence of intramolecular cyclization was revealed in the case of the more exhaustively protected tricarbobenzoxy-L-arginine upon like condensation, via its mixed carbonic-carboxylic acid anhydride derivative, with the benzyl ester derivatives of L-alanine, L-aspartic acid, L-glutamic acid, glycine, L-isoleucine, D-alloisoleucine, 1,-leucine, L-phenylalanine, L-tyrosine and L-valine. Catalytic hydrogenolysis of the tricarbobenzoxy-L-arginylammo acid benzyl esters so procured led to the corresponding dipeptides, which were isolated in high over-all yield. A comparable condensation between tricarbobenzoxy-L-arginine and benzyl Nπ-carbobenzoxy-L-argininate permitted the ultimate synthesis of L-arginyl-L-arginine, which was isolated and characterized as its diflavianate and dipicrolonate derivatives. © 1959, American Chemical Society. All rights reserved. (EN)
English
https://creativecommons.org/licenses/by-nc/4.0/
University of Athens
Pergamos Digital Library
Journal Article



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