Oligosaccharides derivatization

Guttman, A. and Pritchett, T., Capillary gel electrophoresis separation of high-mannose type oligosaccharides derivatized by l-aminopyrene-3,6,8-trisul-fonic acid, Electrophoresis, 16, 1906, 1995. 

J. P. Thompson and C.-L. Schengrund, Oligosaccharide-derivatized dendrimers Defined multivalent inhibitors of the adherence of the cholera toxin B subunit and the heat labile enterotoxin of E. coli to GM1, Glycoconjug. J., 14 (1997) 837-845. 

Suzuki et al. [57] systematically compared the responses of some oligosaccharides derivatized with PA, ABEE, PMP, 4-methoxyphenyl-3-methyl-5-pyrazolone, 2-aminoethanethiol, and 2-aminobenzenethiol in continuous-infusion ESl-MS and frit-FAB-MS. In ESl-MS, the PMP derivatives gave the best results. Reductively aminated oligosaccharides can be analysed as [M+H]" or [M+Na]" in positive-ion ESl-MS and as [M-H] in negative-ion ESl-MS. 

In complex matrices, the insufficient specificity at 200 nm and the low sensitivity of direct UV detection make the analysis of carbohydrates more difficult. Therefore, derivatization of carbohydrates with a suitable agents is still a preferred approach for the detection of monosaccharides and oligosaccharides. Derivatization agents like 2-aminopyridine, 8-aminonaphthalein-l,3,6-trisulfonate (ANTS) or 8-aminopyren-l, 3,6-trisulfonate... 

High pH anion exchange chromatography (HPAEC) has been applied to the separation of neutral V-linked oligosaccharides, oligosaccharides derivatized by p-nitrobenzylhydroxylamine and various D-mannose derivatives. In the last case the relationship between retention times and structure was examined. ... 

Figure 6 Separation of nwno- and oligosaccharides derivatized with ethyl p-aminobenzoate. Capillary fused silica, L=72cm,...

Morelle, W. MlCHALsm, J.-C. Sequencing of oligosaccharides derivatized with benzylamine using electrospray ionisation-quadrupole time of flight-tandem mass spectrometry. Electrophoresis 2004, 25, 2144-2155. 

A derivatization with acid chlorides is also possible. Amino acids can be derivatized with 9-fluorenylmethyl chloroformate (FMOC) and separated on a CSP with X-cyclodextrin (ChiraDex gamma ), a cyclic oligosaccharide which consists of eight glucose units. 

Mo, W., Sakamoto, H., Nishikawa, A., Kagi, N., Langridge, J.I., Shimonishi, Y., and Takao, T., Structural characterization of chemically derivatized oligosaccharides by nanoflow electrospray ionozation mass spectrometry, Anal. Chem., 71, 4100, 1999. 

Gray, G.R. (1974) The direct coupling of oligosaccharides to proteins and derivatized gels. Arch. 

Kallin, E., Lonn, H., Norberg, T., and Elofsson, M. (1989) Derivatization procedures for reducing oligosaccharides, Part 3 Preparation of oligosaccharide glycosylamines, and their conversion into oligosaccharide-acrylamide copolymers./. Carbohydr. Chem. 8, 597-611. 

O Shannessy, D.J., and Wilchek, M. (1990) Immobilization of glycoconjugates by their oligosaccharides Use of hydrazido-derivatized matrices. Anal. Biochem. 191, 1-8. 

To allow all culture production to be controlled, a method for rapid analysis is required. Prior to development of an LC-MS method, the analysis was both complex and time-consuming, involving the purification of a relatively large amount of the antibody using affinity chromatography, enzymatic release, and subsequent derivatization of the oligosaccharides and their analysis by using capillary electrophoresis. 

The CDA protecting group has been shown to withstand common sugar derivatization reactions,1 2 3 4 and is easily removed under acidic conditions.4 Further, it has proved possible to tune the reactivity of sugars via the introduction of the CDA protecting group, and this in turn has allowed concise syntheses of complex oligosaccharides.5... 

Pfenninger, A. Karas, M. Finke, B. Stahl, B. Stractural Analysis of Un-derivatized Neutral Human Milk Oligosaccharides in the Negative Ion Mode by Nano-ESl MS (Part 1 Methodology). J. Am. Soc. Mass Spectrom. 2002, 13, 1331-1340. 

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