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

G Cardillo; A Gennari; L Gentilucci; E Mosconi; A Tolomelli; S Troisi

doi:DOI 10.1016/j.tetasy.2009.12.021

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

G Cardillo, A Gennari, L Gentilucci, E Mosconi, A Tolomelli, S Troisi

Research output: Contribution to journal › Article › peer-review

Abstract

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

Original language	English
Pages (from-to)	96-102
Number of pages	7
Journal	Tetrahedron-Asymmetry
Volume	21
Issue number	1
DOIs	https://doi.org/DOI 10.1016/j.tetasy.2009.12.021
Publication status	Published - 2010

Keywords

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

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DOI 10.1016/j.tetasy.2009.12.021

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

abstract = "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",

keywords = "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",

author = "G Cardillo and A Gennari and L Gentilucci and E Mosconi and A Tolomelli and S Troisi",

note = "566EC Times Cited:3 Cited References Count:78",

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doi = "DOI 10.1016/j.tetasy.2009.12.021",

language = "English",

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T1 - Synthesis of chiral non-racemic intermediates and Arg-Gly-Asp mimetics by CaLB-catalyzed resolution

AU - Cardillo, G

AU - Gennari, A

AU - Gentilucci, L

AU - Mosconi, E

AU - Tolomelli, A

AU - Troisi, S

N1 - 566EC Times Cited:3 Cited References Count:78

PY - 2010

Y1 - 2010

N2 - 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

AB - 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

KW - candida-antarctica-lipase

KW - beta-amino acids

KW - nonpeptide alpha(v)beta(3) antagonists

KW - organic-solvents

KW - biological evaluation

KW - enzymatic resolution

KW - rgd mimetics

KW - stereoselective-synthesis

KW - conformational-analysis

KW - integrin antagonists

U2 - DOI 10.1016/j.tetasy.2009.12.021

DO - DOI 10.1016/j.tetasy.2009.12.021

M3 - Article

SN - 0957-4166

VL - 21

SP - 96

EP - 102

JO - Tetrahedron-Asymmetry

JF - Tetrahedron-Asymmetry

IS - 1

ER -

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

Abstract

Keywords

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