27086-15-3Relevant articles and documents
A new method of orthoesterification, under kinetic control, at non-anomeric positions. Application to the D-glucose and D-mannose series and selective hydrolysis of the corresponding orthoesters
Bouchra,Calinaud,Gelas
, p. 227 - 237 (1995)
The reaction of ketene acetals with D-glucose, D-mannose, and their methyl glycosides is described as a new route to unusual cyclic orthoesters (at non anomeric positions). The reaction proceeds by preferential attack of the reagent on the primary hydroxyl group. The synthesis of strained rings (2,3-diequatorial orthoester) is possible. The resulting methoxyethylidene derivatives are very sensitive to hydrolysis, and mild conditions lead to hydroxyacetates that are potentially useful intermediates for carbohydrates synthesis.
Synthesis of uniformly deuterated n-dodecyl-β -d-maltoside (d39 -DDM) for solubilization of membrane proteins in TROSY NMR experiments
Hiruma-Shimizu, Kazumi,Kalverda, Arnout P.,Henderson, Peter J. F.,Homans, Steve W.,Patching, Simon G.
, p. 737 - 743 (2015/02/19)
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.
