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- W1977059029 abstract "Abstract Tripeptides with cyclic dipeptide backbones, cyclo[ l -Glu( l -Leu-O Bzl)-t-His] and cyclo[ l -Glu( l -Leu-OH)-Ir His, and the corresponding tripeptides with linear backbones, Me3COCO- l -Glu( l -Leu-OBzl)- l -His-OMe and Me3COCO- l -Glu( l -Leu-OH)- l -His-OMe, were synthesized and used as catalysts for the hydrolysis of carboxylic acid active esters of various types. The experimental results are summarized as follows. (I) In the hydrolysis of a neutral and hydrophobic substate, p-nitrophenyl laurate, in 20% dioxane/H2O mixture of pH 7.8, a hydrophobic and flexible peptide, Me3COCO- l -Glu( l -Leu-OH)- l -His-OMe, was more reactive than imidazole. On the other hand, cyclo[ l -Glu( l -Leu-OBzl)- l -His] and cyclo[ l -Leu-OH)- l -His], which have rigid backbone chain and fixed sidechain conformation, were not particularly reactive. (2) in the solcolysis of a positively charged substrate, p-nitrophenyl glycinate hydrochloride, in 42% i-PrOH/H2O mixture at pH 6.95, a positively charged substrate, p-nitrophenyl glycinate hydrochloride, in 42% i-PrOH/H2O mixture at pH 6.95, a negatively charged and flexible peptide, Me3COCO- l -Glu( l -Leu-OH)- l -His-OMe, was more reactive than imidazole. However, cyclo [ l -Glu( l -Leu-OH)- l -His] was not particularly reactive in the same reaction. In the hydrolysis of p-nitrophenyl glycinate hydrochloride in aqueous solution at pH 7.8 a hydrophobic and rigid peptide, cyclo[( l -Glu( l -Leu-OBzl)- l -His], was more reactive than imidazole. However, in the hydrolysis of p-nitrophenyl CO-AMINODODECANOATE hydrochloride, which has a positive charge and a rective site separated by a long hydrophobic chain, peptide catalysts did not show efficient catalysis. (3) In the hydrolysis of a positively charged, hydrophobic and chiral substrate, p-nitrophenyl leucinate hydrochloride, in aqueous solution at pH 6.95, the d -enantiomer was hydrolysed more quickly that the t-enantiomer with cyclo[ l -Glu( l -Leu-OBzl) l -His] or cyclo[t-Glu( l -Leu-OH)- l -His] as catalyst. On the other hand, the tripeptides with linear backbone did not effect an enantiomer-selective catalysis. The solvolytic reaction catalysed by the tripeptides with cyclic dipeptide backbone in 42% i-PrOH/water mixture was also enantiomer-selective." @default.
- W1977059029 created "2016-06-24" @default.
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- W1977059029 date "1982-08-01" @default.
- W1977059029 modified "2023-09-24" @default.
- W1977059029 title "Enantiomer-selective solvolysis catalysed by a histidine-containing cyclic dipeptide carrying chiral side chain" @default.
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- W1977059029 doi "https://doi.org/10.1016/0141-8130(82)90058-7" @default.
- W1977059029 hasPublicationYear "1982" @default.
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