Sugars aldonitrile acetates

A newer technique which shows promise but has not yet been fully tested is based upon the preparation and separation of aldonitrile acetates of reducing sugars (Equation 9.12). The dried sugar is dissolved in pyridine and treated with hydroxylamine hydrochloride in a sealed glass ampoule at 90°C for 0.5 hr. The mixture is cooled, acetic anhydride added, and another 30-min reaction is carried out in the resealed ampoule. Actual formation of the nitrile may occur in the injector of the gas chromatograph. Nonreducing sugars apparently do not form the nitrile but are present as the... 

Aldonitrile acetates of sugars have been applied to their GC analysis in different polysaccharides [442] on LAC-4R-886 polyester stationary phase (190°C)and to the analysis of polyols and aldoses in urine and crystalline lenses [444] on a capillary column of borosilicate glass (60 m X0.3 mm l.D.) coated with SE-30 containing a dispersion of Silanox 101 (temperature programming at l°C/min from 150°C). These derivatives were very stable and a uniform product was formed from every individual substrate. 

Acyl groups have a protective role in some synthetic reactions. Gluconic acid nitrile acetates (aldonitrile acetates) are analytically suitable sugar derivatives for gas chromatographic separation and identification of sugars. An advantage... 

Sugar separation by GC requires the preparation of volatile derivatives. Tappi Test Method T 249 pm-75 uses the alditol acetate derivitization (40). Peracetylated aldonitrile (4J) or trimethylsilane (42, 43) derivatives can also be prepared and separated by GC. Wood sugar analysis by GC may be useful for specialized problems, but the derivitization steps make it a time-consuming method for routine work. 

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