10.1021/jo0010577.s001
Dominique Bonnet
Dominique
Bonnet
Nathalie Ollivier
Nathalie
Ollivier
Hélène Gras-Masse
Hélène
Gras-Masse
Oleg Melnyk
Oleg
Melnyk
Chemoselective Acylation of Fully Deprotected Hydrazino Acetyl
Peptides. Application to the Synthesis of Lipopeptides
American Chemical Society
2000
acid succinimidyl esters
hydrazino
pH
p K
peptide
acetyl
hydrazine moiety
Deprotected Hydrazino Acetyl Peptides
2000-12-22 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Chemoselective_Acylation_of_Fully_Deprotected_Hydrazino_Acetyl_Peptides_Application_to_the_Synthesis_of_Lipopeptides/3686604
Fully deprotected N-terminal α-hydrazino acetyl peptides were synthesized and chemoselectively
acylated on the hydrazine moiety with various fatty acid succinimidyl esters or <i>N</i>-(cholesterylcarbonyloxy) succinimide to give lipopeptides of high purity. The buffer and pH were adjusted in order
to minimize the oxidation of the hydrazine moiety and to achieve the best conversion and selectivity.
The acylation was performed in a citrate−phosphate buffer/2-methylpropan-2-ol mixture of pH
5.1. The p<i>K</i><sub>a</sub> of the α-hydrazino acetyl group on our model peptide was found to be 6.45, i.e., about
2 units lower than the p<i>K</i><sub>a</sub> of a glycyl residue. The reaction was subsequently applied to the synthesis
of a 38AA peptide derivatized by a palmitoyl group.