Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution |
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Authors: | Giuliana Cardillo Arianna Gennari Luca Gentilucci Elisa Mosconi Alessandra Tolomelli Stefano Troisi |
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Institution: | Department of Chemistry ‘G.Ciamician’, University of Bologna Via Selmi 2, 40126 Bologna, Italy |
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Abstract: | The reactivity of both the ester and amine functions present in β-amino esters was tested in order to obtain the synthesis of enantiopure αvβ3 and α5β1 integrin ligands. CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic β-amino esters, allowing the isolation of intermediates for the preparation of Arg-Gly-Asp (RGD) mimetic compounds. In particular, a CaLB-catalyzed amidation reaction with unprotected p-aminobenzylamine reduced the number of synthetic steps, thus avoiding protection and deprotection of the intermediate compounds. Following this procedure, RGD mimetics were isolated with high yields and enantiomeric purities. |
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