PAPER: A cleavable amino-thiol linker for reversible linking of amines to DNA

Højfeldt, J. W.; Blakskjær, P.; Gothelf, K. V.

J. Org. Chem. 2006, 71, 9556–9557, doi: 10.1021/jo0619736

Center for Catalysis and Interdisciplinary Nanoscience Center (iNANO), Department of Chemistry, University of Aarhus, Langelandsgade 140, 8000 Aarhus C, Denmark

Department of Chemistry, University of Michigan, 930 N. University, Ann Arbor, Michigan 48109-1055

Vipergen, Fruebjergvej 3, DK-2100, Copenhagen OE


A cleavable heterobifunctional cross-linker for the reversible conjugation of amines to thiol-modified DNA has been developed and tested. The succinimidyl 2-(vinylsulfonyl)ethyl carbonate (SVEC) was prepared in three steps and tested for its ability to react with amines and thiols. The linker was efficient for binding leucine to a thiol-modified DNA sequence and for releasing the amino acid at pH 11.8.

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