High-performance liquid chromatography of reducing carbohydrates as strongly ultraviolet-absorbing and electrochemically sensitive 1-phenyl-3-methyl-5-pyrazolone derivatives.

We found that 1-phenyl-3-methyl-5-pyrazolone reacts with reducing carbohydrates almost quantitatively to yield 2:1 compounds having no stereoisomers, which strongly absorb the uv light at 245 nm and are easily oxidizable on a glassy carbon electrode. Reverse-phase partition chromatography on a column of Capcell Pak C18 with uv or electrochemical detection allowed rapid analysis of aldoses and N-acetylhexosamines with the detection limit of 1 pmol or 100 fmol, respectively. This method proved especially useful for analysis of component monosaccharides of glycorproteins. It was also shown to be valid for separation of reducing oligosaccharides; maltodextrins with a degree of polymerization up to 19 were similarly derivatized and separated on this stationary phase.

[1]  R. M. V. Effen,et al.  Determination of carbohydrates by liquid chromatography with oxidation at a nickel(III) oxide electrode , 1986 .

[2]  S. Honda High-performance liquid chromatography of mono- and oligosaccharides. , 1984, Analytical biochemistry.

[3]  J. Kennedy,et al.  Analysis of phenyldimethylsilyl derivatives of monosaccharides and their role in high-performance liquid chromatography of carbohydrates , 1983 .

[4]  R. Spiro,et al.  THE CARBOHYDRATE COMPOSITION OF THE THYROGLOBULINS FROM SEVERAL SPECIES. , 1965, The Journal of biological chemistry.

[5]  T. Ikenaka,et al.  Structure analyses of oligosaccharides by tagging of the reducing end sugars with a fluorescent compound. , 1978, Biochemical and biophysical research communications.

[6]  O. Tarutani,et al.  Purification of hog thyroglobulin. , 1961, Journal of biochemistry.

[7]  M. Batley,et al.  Sensitive analysis of aldose sugars by reversed-phase high-performance liquid chromatography , 1982 .

[8]  S. Ganno,et al.  Rapid, automated analysis of monosaccharides by high-performance anion-exchange chromatography of borate complexes with fluorimetric detection using 2-cyanoacetamide. , 1981, Analytical biochemistry.

[9]  C. Bush,et al.  High-performance liquid chromatographic separation of amino sugars and peptides with metal ion-modified mobile phases , 1982 .

[10]  S. Ganno,et al.  Sensitive ultraviolet monitoring of aldoses in automated borate complex anion-exchange chromatography with 2-cyanoacetamide. , 1981, Analytical biochemistry.

[11]  R. Townsend,et al.  Monosaccharide analysis of glycoconjugates by anion exchange chromatography with pulsed amperometric detection. , 1988, Analytical biochemistry.

[12]  Shigeo Suzuki,et al.  Electrochemical detection of reducing carbohydrates in high-performance liquid chromatography after post-column derivatization with 2-cyanoacetamide , 1984 .

[13]  S. Honda,et al.  Common conditions for high-performance liquid chromatographic microdetermination of aldoses, hexosamines, and sialic acids in glycoproteins. , 1984, Analytical biochemistry.

[14]  G. Tettamanti,et al.  Purification and characterization of bovine and ovine submaxillary mucins. , 1968, Archives of biochemistry and biophysics.

[15]  R. K. Cannan,et al.  The hydrogen ion dissociation curve of the crystalline albumin of the hen's egg. , 1936, The Biochemical journal.

[16]  J. Kennedy,et al.  Analysis of derivatives of carbohydrates by high-pressure liquid chromatography , 1979 .

[17]  K. Nakanishi,et al.  Characterization of methyl glycosides at the pico- to nano-gram level , 1983 .