Two new photoactivable heterobifunctional reagents, l-azido-5-naphthalene sulfonyl chloride (ANS-Cl) and the A-hydroxysuccinimide ester of l-azido-5-naphthalene sulfonyl aminopropionate (NHS-ANS-AP), were synthesized and characterized. The reagents were applicable to the group- directed modification of ligands. Upon exposure to ultraviolet light, the non-fluorescent modified ligands generated reactive nitrene intermediates which could react with neighboring molecules to form fluorescent products. This was demonstrated by the covalent modification of bovine serum albumin with ANS-AP by photolysis. NHS-ANS-AP was used for the preparation of a photoreactive invertebrate lectin.
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