title: Water-driven ligations using cyclic amino squarates: a class of useful SN1-like reactions.
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(N)1 reactions. The structural versatility of the reactants allows the potential recognition of selected amino acid residues on proteins.
authors.affiliation: Department of Chemistry, Syracuse University, Syracuse, NY 13244, USA.
authors.forename: Dawei
authors.initials: D
authors.lastname: Cui
authors.forename: Deepali
authors.initials: D
authors.lastname: Prashar
authors.forename: Preeti
authors.initials: P
authors.lastname: Sejwal
authors.forename: Yan-Yeung
authors.initials: YY
authors.lastname: Luk
mesh_terms: D003500:Cyclization; D003503:Cyclobutanes / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry; D008239:Lysine / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014867:Water / Q000737:chemistry*
chemical_list: D003503:Cyclobutanes; D014867:Water; D008239:Lysine; D003545:Cysteine; C030042:squaric acid