Oligosaccharide alditols

Many bacterial polysaccharides contain phosphoric ester groups. There is a limited number of examples of monoesters. More common are phosphoric diesters, connecting an amino alcohol or an alditol to the polysaccharide chain. Another possibility is that oligosaccharide or oligosaccharide-alditol repeating units are connected to a polymer by phosphoric diester linkages. In addition to the intracellular teichoic acids, several bacteria, for example, different types of Streptococcus pneumoniae, elaborate extracellular polymers of this type. These polymers are generally discussed in connection with the bacterial polysaccharides. 

PA-1 was partially hydrolyzed with O.IM TFA (40°C, 24 h) and the three fractions (PA-l-I, PA-l-II and PA-l-III) were obtained by Bio-gel P-6. Especially, about 50% of TBA-positive material (PA-l-III) was eluted in the fraction of small oligosaccharide. Permethylated oligosaccharide-alditols from PA-l-III were analyzed by GC-EIMS, and three disaccharide-alditols (IP, 2P and 3P) were detected. EI-MS and component sugar analysis suggested that the major peak, IP was Rha-(l- 5)-Kdo-ol and the minor peaks, 2P and 3P were two epimers of Araf-( l->5)-Dha. 

Figure 2 (A) Effect of lithium-degradation on anti-complementary activity of PG-lc (B) Anti-complementary activity of oligosaccharide-alditols obtained from PG-lc by lithium degradation...

Figure 3 Mitogenic activity of products and oligosaccharide-alditols from PG-lc by lithium degradation...

The oligosaccharide-alditols in PG-lc-4 were analyzed by GC-MS as permethylated oligosaccharide-alditols. The results indicated that PG-lc-4 contained di- to tetrasaccharide-alditols possessing glycosyl units such as Hex-(l- 4)-6-deoxyHex-ol, Pen->Pen->deoxyHex-ol, Pen- Hex->deoxyHex-ol, Hex->Hex- Hex-ol,... 

Alkaline conditions are used so frequently in carbohydrate separations on CarboPac columns that it should be pointed out that acidic conditions are suitable for separation of acidic sugars. Figure 24 shows the separation of sialic acid containing oligosaccharides.256 Alkaline conditions were used for neutral milk oligosaccharides and mucin oligosaccharide alditols were characterized similarly.257 The carbohydrates released from yeast mannopro-tein with N-acetyl-P-D-glucosaminidase were also fractionated on CarboPac ... 

Reddy, G. P. and Bush, C. A., High-performance anion exchange chromatography of neutral milk oligosaccharides and oligosaccharide alditols derived from mucin glycoprotein, Anal. Biochem., 198, 278, 1991. 

M. Davies, K. D. Smith, A. M. Harbin, and E. F. Hounsell, High-performance liquid chromatography of oligosaccharide alditols and glycopeptides on a graphitized carbon column, J. Chromatogr., 609 (1992) 125-131. 

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

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. 

The most easily recognizable fragment ions in the mass spectra of permethylated oligosaccharide alditols are those from nonreducing units, i.e., fragment ions at m/z 219 for permethylated hexose, m/z 189 for permethylated deoxyhexose, m/z 175 for permethylated pentose, m/z 233 for permethylated... 

N.G. Karlsson, B.L. Schulz, N.H. Packer, Structural determination of neutral O-linked oligosaccharide alditols by negative-ion LC-ESI-MS", J. Am. Soc. Mass Spectrom., 15 (2004)659. 

Figure 20.4 Base-peak chromatogram of RNase B oligosaccharide alditols, acquired using a graphitized carbon column in LC-MS. Peak annotation (a)...

W. Morelle, J. Lemoine, G. Strecker, Structural analysis of 0-linked oligosaccharide-alditols by ESI-MS-MS after mild periodate oxidation and derivatization with 2-PA, Anal. Biochem., 259 (1998) 16. 

---