3242-70-4Relevant academic research and scientific papers
Fast and convenient synthesis of α-N-protected amino acid hydrazides
Verardo, Giancarlo,Geatti, Paola,Lesa, Barbara
, p. 559 - 564 (2007/10/03)
A fast, simple and convenient synthesis of α-N-protected amino acid hydrazides is reported. The procedure involves the reaction between hydrazine monohydrate and the mixed anhydride obtained from an α-N-protected amino acid and ethyl chloroformate. When m
Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis
Voelkert, Martin,Koul, Surrinder,Mueller, Gernot H.,Lehnig, Manfred,Waldmann, Herbert
, p. 6902 - 6910 (2007/10/03)
The enzymatic cleavage of amino acid phenylhydrazides with the enzyme tyrosinase (EC 1.14.18.1) offers a new, mild, and selective method for C-terminal deprotection of peptides. The advantages of the described methodology are the very mild oxidative removal of the protecting group at room temperature and pH 7, a high chemo- and regioselectivity, and the availability of the biocatalyst. Even in oxygen-saturated solution, the oxidation of sensitive methionine residues was not observed. These features make the methodology suitable for the synthesis of sensitive peptide conjugates. Mechanistic data suggest that the hydrolysis of the oxidized adducts proceeds by a free-radical mechanism.
PAPAIN-CATALYZED SYNTHESIS OF PHENYLHYDRAZIDES OF N-ACYLAMINO ACIDS
Cerovsky, Vaclav,Jost, Karel
, p. 2557 - 2561 (2007/10/02)
Phenylhydrazides of Nα-acyl derivatives of all coded amino acids, except proline, were prepared by papain (E.C. 3.4.22.2)-catalyzed synthesis.Comparison of yields affords information about the suitability of the amino acid in position P1/
