Alditols spectrometry

Steinberg, R, and Fox, A. (1999), Automated derivatization instrument Preparation of alditol acetates for analysis of bacterial carbohydrates using gas chromatography-mass spectrometry, Anal. Chem.,11,1914-1917. 

The proposed structure is in full agreement with the results obtained by mass spectrometry, immunodiffusion and analysis of partially methylated alditol acetates (4). 

Figure 1. Methylation linkage analysis of PSL-I by GC/MS total ion chromatogram of partially methylated alditol and myoinositol acetates (PMAA) from PSL-I carboxyl-reduced trisaccharide by gas chromatography /mass spectrometry in...

M. McNeil, Elimination of internal glycosyl residues during chemical ionization-mass spectrometry of per-O-alkylated oligosaccharide-alditols, Carbohydr. Res., 123 (1983) 31-40. 

Plasma-desorption mass spectrometry is another technique that has been applied successfully to the detection of readily removable fatty acyl substituents in intact glycolipids and their acylated derivatives. The specific location of the fatty acyl substituents in the ring of the glycosyl residues, as in LOS antigens, is determined by methylation under nonbasic conditions (see Section II.lb), followed successively by O-deacylation, ethylation of the exposed hydroxyl groups, and GC-MS analysis of partially alkylated alditol acetates21 ethyl groups denote the sites of previous O-acylation. 

M. K. Fatema, H. Nonami, D. R. B. Ducatti, A. G. Gonqalves, M. E. R. Duarte, M. D. Noseda, A. S. Cerezo, R. Erra-Balsells, and M. C. Matulewicz, Matrix-assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry analysis of oligosaccharides and oligosaccharide alditols obtained by hydrolysis of agaroses and carrageenans, two important types of red seaweed polysaccharides, Carbohydr. Res., 345 (2010) 275-283. 

M. R. Cases, C. A. Stortz, and A. S. Cerezo, Separation and identification of partially ethylated galactoses as their acetylated aldononitriles and alditols by capillary gas chromatography and mass spectrometry,/. Chromatogr., 662 (1994) 293-299. 

Whiton, R. S., Lau, P., Morgan, S. L., Gilbart, J., and Fox, A. (1985). Modifications in the alditol acetate method for analysis of muramic acid and other neutral and amino sugars by capillary gas chromatography-mass spectrometry with selected ion monitoring. /. Chromatogr. A 347, 109—120. 

Carpita NC, Shea EM (1989) Linkage structure of carbohydrates by gas chromotography-mass spectrometry (GC-MS) of partially methylated alditol acetates. In Biermann CJ, McGinnis GD (eds) Analysis of carbohydrates by GLC and MS. CRC Press, Boca Raton, FL, p 157... 

Methylation is the most widely used method to determine the position of the glycosyl linkages.Permethylation of glycolipids can be done according to the methods of Hakomori (32) and Ciucanu and Kerek (33). The permethylated derivatives are hydrolyzed and the products converted into partially methylated alditol acetates and identified by gas chromatography-mass spectrometry ( CG-MS) (34). 

Funakoshi, I., Yamashina, I. (1980). Quantitative determination of partially methylated alditol acetate of amino sugar by gas chromatography-mass spectrometry. Analytical Biochemistry, 107, 265 270. 

Analysis of a hydrolyzate of the lipopolysaccharide from Pasteurella pseudotuberculosis Group IIA, by g.l.c. of the derived alditol acetates, revealed an unknown component. Mass spectrometry of the alditol acetate obtained after reduction with sodium borodeuteride showed a fragmentation mode compatible with the alditol acetate from a 6-deoxy-heptose. The sugar was subsequently identified as 6-deoxy-D-manno-heptose. ... 

Methyl glycosides are of their greatest use when only a few methylated sugars are anticipated, as with polysaccharides of simple structure and, in particular, with oligosaccharides. They are useful where identification must be based on peak profile and retention times, but, when characterization is to be achieved by mass spectrometry, other derivatives, such as alditol acetates, are preferable (see Section XXI,2 p. 30). Glycosides have the advantage over alditols that they may be hydrolyzed to the free sugar for further characterization. 

With the advent of column packings capable of separating alditol acetates (see Part I, Section VII,2 p. 59), these derivatives were first utilized by Lindberg and coworkers, who showed that the same liquid phase (ECNSS-M) is suitable for the separation of these compounds having all degrees of methylation. The simplicity of the chromatogram, coupled with the fact that the pattern of methylation in alditol acetates may readily be determined by mass spectrometry (see Section XXV ... 

Reduction of some methylated sugars produces a symmetrical alditol this can introduce ambiguities when the pattern of substitution is to be determined by mass spectrometry (see Section XXV p. 37). Such problems are obviously avoided by (he use of didiioacetals or nitriles. For this reason, Dmitriev and coworkers investigated both the g.l.c. and mass spectrometry of acetylated nitriles. 

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