Heterotrifunctional compounds for photoaffinity labelling

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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548548, 546294, 552 8, C07C24716, C07C24718, C07D207452

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active

056463022

ABSTRACT:
The invention is concerned with novel heterotrifunctional compounds which contain a chemically reactive group R, a photochemically reactive group Ar--N.sup.3 and a reductively cleavable S--S(X.sub.2)-group. The chemically reactive group and the photochemically reactive group are separated by a spacer group which contains a disulfide group. The water-solubilizing groups are carboxylic acids and sulfonic 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.

REFERENCES:
patent: 4784804 (1988-11-01), Basch et al.
patent: 4784805 (1988-11-01), Blattner
patent: 5162505 (1992-11-01), Dean et al.
Clement, et al., Biochemistry, 19:2196-2203 (1980) "Photoaffinity Labeling of Insulin Analogue Selectively Modified at the Amino Terminal of the B Chain".
Jung, et al., Biochimica et Biophysica Acta, 761:152-162 (1983) "Crosslinking of Platelet Glycoprotein by N-Succinimidyl".
Pele, et al., J. of Biol. Chem., 256:5064-5070 (1981) "A New Heterobifunctional Cross-linking Reagent for the Study of Biol. Interactions betw. Proteins".

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