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This work reports the first synthesis of uniformly deuterated n-dodecyl--d-maltoside (d(39)-DDM). DDM is a mild non-ionic detergent often used in the extraction and purification of membrane proteins and for solubilizing them in experimental studies of their structure, dynamics and binding of ligands. We required d(39)-DDM for solubilizing large -helical membrane proteins in samples for [N-15-H-1]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d(39)-DDM used d(7)-d-glucose and d(25)-n-dodecanol to introduce deuterium labelling into both the maltoside and dodecyl moieties, respectively. Two glucose molecules, one converted to a glycosyl acceptor with a free C4 hydroxyl group and one converted to a glycosyl donor substituted at C1 with a bromine in the -configuration, were coupled together with an (14) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the -configuration to give DDM. H-1 NMR spectra were used to confirm a high level of deuteration in the synthesized d(39)-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.
Author(s): Hiruma-Shimizu K, Kalverda AP, Henderson PJF, Homans SW, Patching SG
Publication type: Article
Publication status: Published
Journal: Journal of Labelled Compounds and Radiopharmaceuticals
Year: 2014
Volume: 57
Issue: 14
Pages: 737-743
Print publication date: 01/12/2014
Online publication date: 09/12/2014
ISSN (print): 0362-4803
ISSN (electronic): 1099-1344
Publisher: John Wiley & Sons Ltd.
URL: http://dx.doi.org/10.1002/jlcr.3249
DOI: 10.1002/jlcr.3249
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