Compounds and methods for the site-specific photoaffinity...

C - Chemistry – Metallurgy – 07 – C

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C07C 323/67 (2006.01) C07C 247/18 (2006.01) C07D 207/416 (2006.01) C07D 207/46 (2006.01) C07D 213/71 (2006.01) G01N 33/532 (2006.01)

Patent

CA 2098959

The invention is concerned with novel heterotrifunctional compounds which contain a chemically reactive group R, a photo-chemically reactive group Ar-N3 and a reductively cleavable S-S(X2)-group. Novel heterotrifunctional compounds are of the general formula: (see formula I) The chemically reactive group and the photo-chemically reactive group are separated by a spacer group which contains a disulphide group. The water-solubilizing groups are e.g. carboxylic acids and sulphonic acids or derivatives thereof which are attached either to the aromatic ring or to the spacer group between the aromatic ring and the cleavable SS group. The compounds facilitate a novel photoaffinity method for the labelling of biomolecules, whereby the labelled biomolecule preserves its water solubility and the labelling molecule preferably projects free into the solution after anchorage to the surface of the biomolecule. The advantageous use of these compounds is illustrated of the basis of the functionalization of biomolecules by introducing an alkylthio function as a special embodiment of a photoaffinity labelling method.

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