Synthesis of uniformly deuterated n-dodecyl-?-D-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments.
 

Synthesis of uniformly deuterated n-dodecyl-?-D-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments.

Related Articles Synthesis of uniformly deuterated n-dodecyl-?-D-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments.

J Labelled Comp Radiopharm. 2014 Dec 9;

Authors: Hiruma-Shimizu K, Kalverda AP, Henderson PJ, Homans SW, Patching SG

Abstract
This work reports the first synthesis of uniformly deuterated n-dodecyl-?-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 ?-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 ?-configuration, were coupled together with an ?(1 -> 4) 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. (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.


PMID: 25491565 [PubMed - as supplied by publisher]



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