Host-guest complexation-37 : Synthesis and binding properties of a transacylase partial mimic with imidazole and benzyl alcohol in place |
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| Affiliation: | 1. Hubei Collaborative Innovation Center for Advanced Organic Chemical Materials, Hubei Key Laboratory on Organic and Polymeric Optoelectronic Materials, Department of Chemistry, Wuhan University, Wuhan 430072, PR China;2. New Materials Technology Institute, Co-Innovation Center for Micro/Nano Optoelectronic Materials and Devices, Chongqing University of Arts and Sciences, Chongqing, 402160, People’s Republic of China;1. Department of Pharmaceutical Sciences, The Daniel K. Inouye College of Pharmacy, University of Hawai’i at Hilo, 34 Rainbow Drive, Hilo, HI 96720, USA;2. Department of Chemical Biology & Therapeutics, St. Jude Children’s Research Hospital, 262 Danny Thomas Place, MS#1000, Memphis, TN 38105, USA;1. Crop Protection Chemicals Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India;2. Centre for Chemical Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India |
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| Abstract: | The design and 30-step synthesis of a transacylase partial mimic is described. The target catalyst combines a macrocyclic binding site, a hydroxymethyl group, and an imidazole group organized to act cooperatively through their attachment to a quaterphenyl support structure. The binding site is composed of three cyclic urea units in a tripod arrangement, rigidified by their incorporation into a macrocycle along with two anisyl and one m-xylyl spacer units. The binding and catalytic sites are complementary to amino acid ester salts. The host catalyst collects and orients through complexation the guest substrate to provide substantial rate enhancements for transacylation of amino ester salts. The free energies are reported for the host in CDCl3 binding the picrate salts of Li+, Na+, K+, Rb+,Cs+, NH4+, CH3NH3+ and t-BuNH3+. |
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