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

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(N)1 reactions. The struct...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2011-01, Vol.47 (4), p.1348-1350
Main Authors: Cui, Dawei, Prashar, Deepali, Sejwal, Preeti, Luk, Yan-Yeung
Format: Article
Language:English
Subjects:
Cyclization
Cyclobutanes - chemistry
Cysteine - chemistry
Lysine - chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Water - chemistry
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Summary: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(N)1 reactions. The structural versatility of the reactants allows the potential recognition of selected amino acid residues on proteins.
ISSN:1364-548X
DOI:10.1039/c0cc03989f