A novel method for specific labelling of carbohydrates with deuterium by catalytic exchange

Invisible detergents for structure determination of membrane proteins by small‐angle neutron scattering

“…for OG): A ) deuterating the alkyl chain at the required deuteration level starting from the corresponding fatty acid and using hydrothermal Pt/C catalysed H/D exchange reactions at 220 °C in the appropriate molar ratio of deuterium and hydrogen atoms in the mixture, reducing the fatty acid molecule to the corresponding alcohol; B ) attaching the deuterated alcohol to the corresponding acetylated bromo‐sugar head group (i.e. 2,3,4,6‐tetra‐O‐acetyl‐α‐D‐glucopyranosyl bromide and 2,3,6,2′,3′,4′,6′‐hepta‐O‐acetyl‐a‐D‐maltosyl bromide) according to standard procedures deacetylation of the sugar head group; C ) deuterating the sugar head to achieve the required deuteration level by using mild conditions of Raney Nickel as a catalyst in D 2 O/H 2 O mixture at 80 °C for 18 h. The latter step allows the incorporation of deuterium atoms on carbons adjacent to free hydroxyl groups (α positions) in the sugar head group with retention of configuration, but it does not affect any H/D back‐exchange at the more inert alkyl chain sites (see Supporting Information 2 for details).…”

“…conditions of Raney Nickel as a catalyst in D 2 O/H 2 O mixture at 80°C for 18 h. The latter step allows the incorporation of deuterium atoms on carbons adjacent to free hydroxyl groups (a positions) in the sugar head group with retention of configuration, but it does not affect any H/D back-exchange at the more inert alkyl chain sites [36][37][38] (see Supporting Information 2 for details).…”

Localization of trehalose in partially hydrated DOPC bilayers: insights into cryoprotective mechanisms

“…Deuterated trehalose was produced by the National Deuteration Facility, ANSTO. This was achieved by catalytic exchange reactions following a procedure of Koch and Stuart using a Raney nickel catalyst [39,40]. Isotopic purity, determined by mass spectrometry and solution NMR, was 67.8% of the 14 non-exchangeable hydrogens in the trehalose molecule.…”

Ruthenium‐Catalysed Epimerisation of Carbohydrate Alcohols as a Method to Determine the Equilibria for Epimer Interconversion in Hexopyranosides

“…In their experiments on the epimerisation of unprotected methyl glycopyranosides with Raney nickel, Koch and Stuart, [24,25] and later Perlin, [22] observed that thermodynamic equilibrium was not reached (i.e. the same composition of the product mixture was not reached starting from each of the components -indeed the same mixture was not seen starting from any two of the components tested), but it is noteworthy that significant α-GlcǞα-Gal and α-GlcǞα-Man epimerisation away from the α-glucoside was seen.…”