Water-driven ligations using cyclic amino squarates: a class of useful SN1-like reactions

Dawei Cui; Deepali Prashar; Preeti Sejwal; Yan-Yeung Luk

doi:10.1039/C0CC03989F

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Water-driven ligations using cyclic aminosquarates: a class of useful S_N1-like reactions†

Dawei Cui,^a Deepali Prashar,^a Preeti Sejwal^a and Yan-Yeung Luk*^a

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* Corresponding authors

^a Department of Chemistry, Syracuse University, Syracuse, USA
E-mail: yluk@syr.edu

Abstract

We report a class of water-soluble and -stable cyclic amino squarates that ligate with cysteine or lysine residues without side-products in an entirely aqueous environment. The ligations include addition–elimination reactions that are promoted by water in a way similar to S_N1 reactions. The structural versatility of the reactants allows the potential recognition of selected amino acid residues on proteins.

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Supplementary files

Experimental procedures and spectral data for all the new compounds PDF (3053K)

Article information

DOI: https://doi.org/10.1039/C0CC03989F
Article type: Communication
Submitted: 20 Sep 2010
Accepted: 26 Oct 2010
First published: 16 Nov 2010

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Chem. Commun., 2011,47, 1348-1350

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Water-driven ligations using cyclic amino squarates: a class of useful S_N1-like reactions

D. Cui, D. Prashar, P. Sejwal and Y. Luk, Chem. Commun., 2011, 47, 1348 DOI: 10.1039/C0CC03989F

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Chemical Communications