A remarkable catalytic effect of the potassium salt of 1-hydroxybenzotriazole on peptide bond formation
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.
Horiki, Kusuo,Murakami, Atsuko
p. 615 - 622
(2007/10/02)
Novel esterifying agents, and their production and use
A process for esterifying organic carboxylic acids which comprises reacting an organic carboxylic acid with a carbonic acid ester of the formula: EQU1 wherein R is an organic group and X and Y are each a negative group in the presence of a basic substance to make esterified the carboxyl group in the organic carboxylic acid. The process is advantageous in affording the objective carboxylic ester in a good yield within a short time by a simple operation under a mild reaction condition.
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(2008/06/13)
The trifluoroacetate method of peptide synthesis. I. The synthesis and use of trifluoroacetate reagents.
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Sakakibara,Inukai
p. 1979 - 1984
(2007/10/05)
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