Kurooka, S., Hashimoto, M., Tomita, M., Maki, A. and Yoshimura, Y. (1976) Relationship between the Structures of S-Acyl Thiol Compounds and Their Rates of Hydrolysis by Pancreatic Lipase and Hepatic Carboxylic Esterase. Journal of Biochemistry, 79, 533-541.

has been cited by the following article:

• TITLE: Effect of the Position of Reaction-Site in Amphipathic-Type Thioester in Aqueous Amidation Reaction

  AUTHORS: Ikumi Otomo, Chiaki Kuroda

  KEYWORDS: Hydrophobic Effect, Amides, Thioesters

  JOURNAL NAME: Advances in Chemical Engineering and Science, Vol.5 No.3, June 30, 2015

  ABSTRACT: Amphipathic-type thioesters CH3(CH2)mCOS(CH2)nCOONa (m + n = 12) were synthesized and their reaction with various alkylamines was examined. Compounds having thioester moiety close to carboxylate (m = 10, n = 2) afforded the corresponding amides in good yields, while the substrate having thioester moiety distant from carboxylate (m = 2, n = 10) afforded the amides in relatively low yield. In all cases, the difference in yield due to the chain length of amine was not observed. The results indicated that the reaction took place effectively near the surface of micelle. However, the reaction was found to occur not only on micelle surface but also in solution.