Carboxymethyl glucose

X.J. Wu and M.M.F. Choi, An optical glucose biosensor based on entrapped-glucose oxidase in silicate xerogel hybridised with hydroxyethyl carboxymethyl cellulose. Anal. Chim. Acta 514, 219-226 (2004). 

Carboxymethyl cellulose is normally used at a degree of substitution of around 0.1 (i.e. the number of hydroxy groups substituted per glucose residue), which renders the polymer water soluble. Further water solubility can be obtained by increasing the degree of substitution. 

Total hydrolysis of the polymers gave D-glucose only. Water-soluble derivatives (ethyl or carboxymethyl ethers) of the polymers were unaffected by a-amylase, but were partially hydrolyzed by a ceUulase preparation from Acdobader xylinum. The optical rotations of several preparations of this polyglucose and of cellulose (P 1150) in tetraethylammonium hydroxide were all 0°, thereby strongly suggesting that the polyglucoses are /S-D-linked.109... 

One interesting innovation described by Reid and Daul100 involves carboxymethylation of the cotton cloth, itself, with chloroacetic acid and alkali, to the extent of one carboxymethyl group per 5 to 40 anhydro-D-glucose units. On such treatment, the cloth showed increased water absorption and a desirable swelling tendency. 

The synthesis of CMDBSSu involves the random carboxymethylation of hydroxyl groups on the glucose units, the benzylamidation of some of the carboxylic groups with benzylamine in the presence of N-ethoxycarbonyl-2-ethoxy-l,2-dihydroquinoline (EEDQ) to carboxymethyl dextran benzylamide (CMDB), the sulfonation of phenyl rings and sulfation of remaining hydroxyl groups at the polymer backbone (Fig. 39, [108,222]). 

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