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N-terminal α-hydrazinoacetylpeptides were synthesized and chemoselectively acylated on the hydrazine moiety with various fatty acid succinimidyl esters or N-(cholesterylcarbonyloxy) succinimide. The acylation was performed in water/2-methyl-propane-2-ol mixtures buffered at pH 5.1. The mild reaction conditions allow the derivatization of peptides by sensitive fatty acids.