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Synthesis of Uniformly Deuterated n-dodecyl-β-D-maltoside (d39-DDM) for Solubilization of Membrane Proteins in TROSY NMR Experiments

Synthesis of Uniformly Deuterated n-dodecyl-β-D-maltoside (d39-DDM) for Solubilization of Membrane Proteins in TROSY NMR Experiments

Kazumi Hiruma-Shimizu, Arnout P Kalverda, Peter J F Henderson, Steve W Homans, Simon G Patching

J Labelled Comp Radiopharm. 2014 Dec;57(14):737-43.

PMID: 25491565

Abstract:

This work reports the first synthesis of uniformly deuterated n-dodecyl-β-D-maltoside (d39-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 d39-DDM for solubilizing large α-helical membrane proteins in samples for [(15)N-(1)H]TROSY (transverse relaxation-optimized spectroscopy) NMR experiments to achieve the highest sensitivity and best resolved spectra possible. Our synthesis of d39-DDM used d7-D-glucose and d25-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 α-configuration, were coupled together with an α(1 → 4) glycosidic bond to give maltose, which was then coupled with n-dodecanol by its substitution of a C1 bromine in the α-configuration to give DDM. (1)H NMR spectra were used to confirm a high level of deuteration in the synthesized d39-DDM and to demonstrate its use in eliminating interfering signals from TROSY NMR spectra of a 52-kDa sugar transport protein solubilized in DDM.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP69227936	n-Dodecyl β-D-maltoside		69227-93-6	Price

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