Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution

The reactivity of both the ester and amine functions present in beta-amino esters was tested in order to obtain the synthesis of enantiopure alpha v beta 3 and alpha 5 beta 1 integrin ligands CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic bet...

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Bibliographic Details
Published in:Tetrahedron: Asymmetry
Main Authors: Cardillo, G, Gennari, A, Gentilucci, L, Mosconi, E, Tolomelli, A, Troisi, S
Format: Article in Journal/Newspaper
Language:English
Published: 2010
Subjects:
candida-antarctica-lipase
beta-amino acids
nonpeptide alpha(v)beta(3) antagonists
organic-solvents
biological evaluation
enzymatic resolution
rgd mimetics
stereoselective-synthesis
conformational-analysis
integrin antagonists
Antarc*
Antarctica
Online Access:https://research.manchester.ac.uk/en/publications/ee769fa1-66e0-4410-94af-ba5712d166c3
https://doi.org/DOI 10.1016/j.tetasy.2009.12.021
Description
Summary:The reactivity of both the ester and amine functions present in beta-amino esters was tested in order to obtain the synthesis of enantiopure alpha v beta 3 and alpha 5 beta 1 integrin ligands CaLB successfully catalyzed both the enantioselective transesterification and the N-acylation of racemic beta-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 beta-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 (c) 2010 Elsevier Ltd All rights reserved

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