Synthesis of uniformly deuterated n-dodecyl-β-d-maltoside (d39-DDM) for solubilization of membrane proteins in TROSY NMR experiments
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....
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Veröffentlicht in: | Journal of labelled compounds & radiopharmaceuticals 2014-12, Vol.57 (14), p.737-743 |
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Sprache: | eng |
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Zusammenfassung: | 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 [15N–1H]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. 1H 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.
The uniformly deuterated non‐ionic detergent n‐dodecyl‐β‐d‐maltoside (d39‐DDM) was synthesized from d7‐d‐glucose and d25‐n‐dodecanol. 1H NMR spectra confirmed a high level of deuteration in the synthesized d39‐DDM and demonstrated its use in eliminating interfering signals of 52‐kDa sugar transport protein solubilized in DDM. |
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ISSN: | 0362-4803 1099-1344 |
DOI: | 10.1002/jlcr.3249 |