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Regio‐ and stereo‐selective deuterium labelling of β‐cyclodextrin
Author(s) -
Djedaïni Florence,
Desalos Jacques,
Perly Bruno
Publication year - 1990
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580280707
Subject(s) - chemistry , deuterium , methylene , labelling , reagent , raney nickel , stereoselectivity , proton , hydrogen–deuterium exchange , medicinal chemistry , organic chemistry , hydrogen , catalysis , biochemistry , physics , quantum mechanics
Reliable methods for the selective deuteration of β‐cyclodextrin are described. Kinetic studies of the proton‐deuterium exchange catalysed by Raney nickel in deuterium oxide show dramatically different behaviours of positions 2, 6 and 3 and allow selective labelling. Deuteration of protons at position 2 can be achieved by performing the exchange procedure at room temperature or preferably at 310 K. Under these conditions, no other positions are affected. At refluxing temperature, protons of the methylene group rapidly exchange and, at longer reaction times, deuteration at C3 takes place. A combination of direct and back exchange cycles affords cyclodextrins labelled on any of the sensitive positions. “Organic shift reagents” are used to assist the NMR analysis of labelled samples and have shown some stereoselectivity for deuteration of the C6 methylene group protons.