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

Chem Commun (Camb). 2011 Jan 28;47(4):1348-50. doi: 10.1039/c0cc03989f. Epub 2010 Nov 16.

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.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cyclization
  • Cyclobutanes / chemistry*
  • Cysteine / chemistry
  • Lysine / chemistry
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Water / chemistry*

Substances

  • Cyclobutanes
  • Water
  • Lysine
  • Cysteine
  • squaric acid