スクシンイミドエステルの化学 (第5報)

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書誌事項

タイトル別名
  • Chemistry of Succinimido Esters. V.
  • スクシンイミドエステル ノ カガク 5 スイヨウエキチュウ デ ノ N スクシ
  • Kinetic Studies on the Reactions of N-Succinimidyl Benzoates with Various Amino Acids in Aqueous Solution
  • 水溶液中でのN-スクシンイミジルベンゾエートと種々のアミノ酸との反応の速度論的研究

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抄録

The reactions of N-succinimidyl benzoates (1) with various amino acids (2) to give the corresponding N- (arylcarbonyl) amino acids (3) were studied kinetically at 25°C and pH=pKa. The formation of (3) was competitive with the decomposition of (1) in aqueous solution; i.e., the rate may be expressed as V= (k1, d+k2 [2]) [1], where k1, d is the first order rate constant for the N-arylcarbonylation of (2) by (1). <BR>The second order rate constant, k2, at pH= pKa, correlated with the nucleophilicity (pKa) of (2), giving slopes of 0.78 0.86 for log k2 vs. pKa plots. The plot of log k2 vs. σ for metasubstituted (1) showed a linear relationship with ρ=0.651.28. The rate of ortho-substituted (1) was smaller than that of meta-substituted (1), because of the steric hindrance of ortho-substituent in (1). The ratios, 10-3k2/k1, d exceeded unity. The above observations demonstrate N-arylcarbonylation involving a nucleonphilic attack of a free amino group on the ester carbonyl carbon in (1) and the possibility of (1) as an N-arylcarbonyl reagent of proteins.

収録刊行物

  • 油化学

    油化学 36 (3), 176-182, 1987

    公益社団法人 日本油化学会

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