125402-93-9Relevant academic research and scientific papers
A remarkable catalytic effect of the potassium salt of 1-hydroxybenzotriazole on peptide bond formation
Horiki, Kusuo,Murakami, Atsuko
, p. 615 - 622 (2007/10/02)
A semiquantitative investigation was done on the catalytic effects of 1-hydroxybenzotriazole (HOBt) (5) and the potassium salt 6 of HOBt (5) on peptide bond formation by the active ester method. HOBt (5) was found to catalyze the aminolysis reaction of two different types of active esters, benzyloxy-carbonyl-l-phenylalanine 2,4,5-trichlorophenyl ester (1) and benzyloxycarbonyl-l-phenylalanine 1-succinimidyl ester (2), in tetrahydrofuran (THF) and in a dipolar aprotic dimethylformamide (DMF) solvent. A large rate enhancement was also observed in the aminolysis reaction of 1 in THF when the potassium salt 6 of HOBt (5) was added in the presence of dicyclohexyl-18-crown-6 (7). The rate acceleration in the aminolysis reaction of the active esters by 5 and 6 may reasonably be explained in terms of nucleophilic catalysis.
