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. 1976 May;73(5):1406–1408. doi: 10.1073/pnas.73.5.1406

2-diazo-3,3,3-trifluoropropionyl chloride: reagent for photoaffinity labeling.

V Chowdhry, R Vaughan, F H Westheimer
PMCID: PMC430303  PMID: 1064014

Abstract

2-Diazo-3,3,3-trifluoropropionyl chloride has been synthesized from trifluorodiazoethane and phosgene. Its derivatives are acid stable, can be used to label enzymes, and undergo photolysis with substantially less rearrangement than do derivatives of other known diazoacyl reagents designed for photoaffinity labeling. In particular, the diazotrifluoropropionyl thioester of methyl N-acetylcysteine undergoes photolysis in methanol with about 40% insertion into the - OH bond of the solvent; by contrast, photolysis of other diazoacyl thioesters gives substantially quantitative Wolff rearrangement. The trifluoro compounds hold promise for the photoaffinity labeling of thiols.

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.

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