PREPARATION OF PROTECTED PEPTIDE HYDRAZIDES FROM THE ACIDS AND HYDRAZINE BY DICYCLOHEXYLCARBODIIMIDE-HYDROXYBENZOTRIAZOLE COUPLING
- 12 January 2009
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 11 (4) , 297-300
- https://doi.org/10.1111/j.1399-3011.1978.tb02852.x
Abstract
A mild procedure for preparing protected peptide hydrazides directly from the corresponding carboxylic acids and equivalent amounts of hydrzaine, N-hydroxybenzotriazole and dicyclohexylcarbodiimide is described. Side reactions frequently encountered in hydrazinolysis are thus totally avoided. The process is especially useful for the preparation of aspartic acid and glutamic acid containing peptide hydrazides. No racemization of the amino acid residue was observed.Keywords
This publication has 15 references indexed in Scilit:
- Fully automated solid phase synthesis of protected peptide hydrazides on recycling hydroxymethyl resinThe Journal of Organic Chemistry, 1976
- The Azide Method in Peptide Synthesis: Its Scope and Limitations1Synthesis, 1974
- p-Alkoxybenzyl Alcohol Resin and p-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide FragmentsJournal of the American Chemical Society, 1973
- Racemisierung bei PeptidsynthesenEuropean Journal of Inorganic Chemistry, 1970
- Selektive Spaltung substituierter Phenylsulfenyl‐Schutzgruppen bei PeptidsynthesenHelvetica Chimica Acta, 1966
- Amino-acids and peptides. XXXIII. Nitrosyl chloride and butyl nitrite as reagents in peptide synthesis by the azide method; Suppression of amide formationCollection of Czechoslovak Chemical Communications, 1961
- Synthesis of Two Protected Hexapeptides Containing the N-Terminal and C-Terminal Sequences of Arginine-Vasopressin1Journal of the American Chemical Society, 1958
- Amino Acids and Peptides. IV. Intermediates for the synthesis of certain cystine-containing peptide sequences in insulinAustralian Journal of Chemistry, 1958
- Studies on Polypeptides. III.1 Novel Routes to α-Amino Acid and Polypeptide HydrazidesJournal of the American Chemical Society, 1952
- Synthetische Versuche mit HippurazidEuropean Journal of Inorganic Chemistry, 1902