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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Photoaffinity heterobifunctional cross-linking reagents based on N-(azidobenzoyl)tyrosines.

New heterobifunctional cross-linking reagents that possessed a photoactive terminus, an electrophilic terminus, and a linking arm between the two termini that had a radiolabeled, enzymatically cleavable bond were synthesized. In a model study, succinimidyl N-[N'-(4-azidobenzoyl)tyrosyl]-beta-alanate ( 16A) was coupled to n-butylamine (a Lys surrogate), iodinated, and cleaved with chymotrypsin in the presence of tyrosylamide to afford the desired adduct (N-(N'-(4-azidobenzoyl)-3-iodotyrosyl)tyrosinamide, thereby demonstrating the feasibility of the enzymatic cleavage. In a biochemical study, succinimidyl N-[N'-(3-azido-5-nitrobenzoyl)tyrosyl]-beta-alanate (16C) was coupled to Lys-75 of calmodulin (CaM), and the radioiodinated monoadduct was successfully photo-cross-linked, in a calcium-dependent manner, to the human erythrocyte plasma membrane Ca2+,Mg2(+)-ATPase and to a synthetic fragment (M13) containing the CaM-binding region of myosin light-chain kinase. In the latter case, densitometry readings indicated 20% cross-linking efficiency.[1]


  1. Photoaffinity heterobifunctional cross-linking reagents based on N-(azidobenzoyl)tyrosines. Imai, N., Kometani, T., Crocker, P.J., Bowdan, J.B., Demir, A., Dwyer, L.D., Mann, D.M., Vanaman, T.C., Watt, D.S. Bioconjug. Chem. (1990) [Pubmed]
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