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Selective 19F-labeling of functionalized carboxylic acids with difluoromethyl diazomethane (CF2HCHN2)​
Citation key 169.2017 Kubyshkin
Author Mykhailiuk, P. and Kishko, I. and Kubyshkin, V. and Budisa, N. and Cossy, J.
Year 2017
DOI 10.1002/chem.201703446​
Journal Chem. Eur. J. [highlighted by cover page / Epub ahead of print]
Abstract The incorporation of fluorinated moieties into organic structures is a particularly powerful approach for generating compounds with useful biological applications in industry, pharmacology, and agriculture. Herein, we report that the recently developed reagent - CF2HCHN2 - selectively esterifies carboxyl groups in organic molecules possessing other polar functional groups. The reaction is remarkably simple, proceeding at room temperature in chloroform without addition of a catalyst. The procedure allows "last-step" incorporation of a fluorinated ester moiety into organic structures, including bioorganic molecules such as peptides and proteins. The fluorinated ester can subsequently function as a 19F-probe in biomolecules, thereby enabling molecular size determination by diffusion 19F-NMR experiments.
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