δ-Unsaturated γ-amino acids: enantiodivergent synthesis and cell imaging studies

Dnyaneshwar Kand; Dinesh Pratapsinh Chauhan; Mayurika Lahiri; Pinaki Talukdar

doi:10.1039/C3CC40824H

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Chemical Communications

Issue 34, 2013

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δ-Unsaturated γ-amino acids: enantiodivergent synthesis and cell imaging studies

Dnyaneshwar Kand,^a Dinesh Pratapsinh Chauhan,^a Mayurika Lahiri^b and Pinaki Talukdar*^a

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Department of Chemistry, Mendeleev Block, Indian Institute of Science Education and Research Pune, India
E-mail: ptalukdar@iiserpune.ac.in ;
Fax: +91 20 2589 9790 ;
Tel: +91 20 2590 8001

Department of Biology, Indian Institute of Science Education and Research Pune, India ;
Fax: +91 20 2589 9790 ;
Tel: +91 20 2590 8001

Chem. Commun., 2013,49, 3591-3593

DOI: 10.1039/C3CC40824H
Received 31 Jan 2013, Accepted 08 Mar 2013
First published online 14 Mar 2013

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Synthesis of both enantiomers of δ-unsaturated γ-amino acids via the enantiodivergent [3,3]-sigmatropic rearrangement strategy is reported. Excellent enantiomeric excess > 94% are observed in the strategy. Cell permeability of a fluorescent amino acid derivative is evaluated by live-cell imaging.

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