Abstract
Oligosaccharides from hyaluronic acid and chondroitin 6-sulfate were prepared by digestion with testicular hyaluronidase and separated according to their degree of polymerization by gel-permeation chromatography. These materials were successively analyzed by negative-mode ion-spray mass spectrometry with an atmospheric-pressure ion source. An ion-spray interface was used to produce ions via the ion evaporation process, producing mass spectra containing a series of molecular species carrying multiple charges. Using two adjacent multiply charged molecular ions, the exact molecular weights up to the tetradecasaccharide were calculated with a precision of ±1 dalton. This type of mass spectrometry was also demonstrated to be feasible for the analysis of mixtures of oligosaccharides, including tetra-, hexa-, octa- and decasaccharides, from hyaluronic acid or chondroitin 6-sulfate without separation. Ion-spray mass spectrometry was thus shown to be applicable to the structural analysis of oligosaccharides from glycosaminoglycans.
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Abbreviations
- HA:
-
hyaluronic acid
- Ch6S:
-
chondroitin 6-sulfate
- GAG:
-
glycosaminoglycan
- GlcA:
-
d-glucuronic acid
- GlcNAc:
-
2-acetamido-2-deoxy-d-glucose
- GalNAc:
-
2-acetamido-2-deoxy-d-galactose.
References
Hascall VC (1981) InBiology of Carbohydrates (Ginsburg V, Robbins, P, eds) Vol. 1, pp 1–49. New York: Wiley.
Rodén L (1980) InThe Biochemistry of Glycoproteins and Proteoglycans (Lennarz WJ, ed) pp 267–371. New York: Plenum.
Lindahl U, Bäckström G, Thumberg L, Leder IG (1980)Proc Natl Acad Sci USA 77:6551–5.
Atha DH, Stephens AW, Rosenberg RD (1984)Proc Natl Acad Sci USA 81:1030–4.
Tollefsen DM, Majerus DW, Blank MK (1982)J Biol Chem 257:2162–9.
Beeley JG (1985) InGlycoprotein and Proteoglycan Techniques (Burdon RH, Van Knippenberg PH, eds) pp 63–93, 225–96. Amsterdam: Elsevier.
Bruins AP, Covey TR, Henion JD (1987)Anal Chem 59:2642–6.
Covey TR, Bonner RF, Shushan BI, Henion J (1988)Rapid Commun Mass Spectrom 2:249–56.
Sakairi M, Kambara H (1989)Anal Chem 61:1159–64.
Nakamura T, Majima M, Kubo K, Takagaki K, Tamura S, Endo M (1990)Anal Biochem 191:21–4.
Cowman, MK, Balazs EA, Bergmann CW, Meyer K (1981)Biochemistry 20:1379–85.
Bitter T, Muir HM (1962)Anal Biochem 4:330–4.
Dische Z, Borenfreund E (1950)J Biol Chem 184:517–22.
Majima M, Nakamura T, Igarashi S, Matsue H, Endo M (1984)J Biochem Biophys Methods 9:245–9.
Terho TT, Hartiala K (1971)Anal Biochem 41:471–6.
Sandford PA, Conrad HE (1966)Biochemistry 5:1508–17.
Taylor RL, Conrad HE (1972)Biochemistry 11:1383–8.
Nagasawa K, Inoue Y, Kamata T (1977)Carbohydr Res 58:47–55.
Stellner K, Saito H, Hakomori S (1973)Arch Biochem Biophys 155:464–72.
Barber M, Bordoli RS, Sedgwick RD, Tyler AN (1982)Biomed Mass Spectrom 9:208–14.
Bush KL, Cooks RG (1982)Science 218:247–54.
Benninghoven A, Jaspers D, Sichterman W (1976)Appl Phys 11:35–39.
Posthumus MA, Kistemaker PG, Meuzelaar HLC, Ten Noever de Brauw MC (1978)Anal Chem 50:985–91.
Torgerson DF, Skowronski RP, Macfarlane RD (1974)Biochem Biophys Res Commun 60:616–21.
Barker SA, Hurst RE, Settine J, Fish FP, Settine RL (1984)Carbohydr Res 125:291–300.
Reinhold VN, Carr SA, Green BN, Petitou M, Choay J, Sinay P (1987)Carbohydr Res 161:305–13.
Carr SA, Reinhold VN (1984)J Carbohydr Chem 3:381–401.
Takagaki K, Nakamura T, Kon A, Tamura S, Endo M (1991)J Biochem (Tokyo)109:514–9.
Takagaki K, Kon A, Kawasaki H, Nakamura T, Tamura S, Endo M (1990)J Biol Chem 265:854–60.
Yanagishita M, Rodbard D, Hascall VC (1979)J Biol Chem 254:911–20.
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Takagaki, K., Kojima, K., Majima, M. et al. Ion-spray mass spectrometric analysis of glycosaminoglycan oligosaccharides. Glycoconjugate J 9, 174–179 (1992). https://doi.org/10.1007/BF00731162
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DOI: https://doi.org/10.1007/BF00731162