Thiols and the diazo group in photoaffinity labels |
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Authors: | Yohtaroh Takagaki Chhitar M Gupta HGobind Khorana |
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Institution: | 1. Department of Biology, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 USA;2. Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139 USA |
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Abstract: | The photoactivable carbene precursor, 2-diazo-3,3,3-tri-fluoro-propionyloxy group, has been introduced recently for light-induced covalent crosslinking in studies of protein-phospholipid interactions in biomem-branes. The diazo group in this reagent has now been shown to undergo reduction in the dark by a number of thiols (dithiothreitol, 2-mercaptoethanol, cysteine and reduced glutathione) used commonly as protective agents for proteins. In contrast, thioglycolate did not cause significant reduction and, therefore, can be safely used as a protective agent. In vesicles formed from phospholipids containing the above photolabel in the fatty acyl chain, dithiothreitol and 2-mercaptoethanol caused reduction. However, cysteine and reduced glutathione caused insignificant reduction of the diazo group, presumably because of their non-permeant nature. |
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Keywords: | DTT dithiothreitol GSH reduced glutathione TGA thioglycolate |
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