Abstract
Shark cartilage proteoglycans bear predominantly chondroitin 6-sulfate. After exhaustive protease digestion, reductive beta-elimination and subsequent chondroitinase ABC digestion, 13 hexasaccharide alditols were obtained from the carbohydrate-protein linkage region and six of them contain 0 or 1 sulfate and/or 1 phosphate residue (Sugahara, K., Ohi, Y., Harada, T., de Waard, P., and Vliegenthart, J. F. G. (1992) J. Biol. Chem. 267, 6027-6035). The other seven compounds, which represent approximately 60% of the isolated linkage hexasaccharides, were analyzed by chondroitinase ACII digestion in conjunction with high performance liquid chromatography and by 500-MHz one- and two dimensional 1H NMR spectroscopy. All seven compounds have the following conventional structure in common. [formula: see text] Two disulfated compounds have an O-sulfate on C-6 of the Gal-2 residue attached to xylitol in combination with an O-sulfate on C-4 or on C-6 of the GalNAc residue. The third disulfated compound has O-sulfate on C-6 of Gal-2, and also on C-6 of Gal-3. Two of the trisulfated compounds also have O-sulfate on C-6 of both Gal-2 and Gal-3 with in addition sulfate on C-6 or C-4 of GalNAc. The other two trisulfated compounds have O-sulfate on C-6 of Gal-2 and on C-4 of Gal-3 in conjunction with sulfate on C-6 or C-4 of GalNAc.
Highlights
Shark cartilage proteoglycans bear predominantly core to which are covalently attached side chains of characchondroitin 6-sulfate
After exhaustive proteasdeiges- teristic sulfated glycosaminoglycansincluding heparin, hepation, reductive@-eliminationand subsequent chondroi- ran sulfate, chondroitin sulfate, dermatan sulfate, and keratan tinase ABC digestion, 13hexasaccharide alditols were sulfate (1).Accumulating evidence indicates that from the obtained from the carbohydrate-protein linkagregion and six of them contain 0 or 1sulfate and/or 1 phosphate residue
The otherseven compounds, which represent approximately 60% of the isolated linkage hexasaccharides, were analyzed by chondroiwide variety of biological functions of proteoglycans some are attributable to glycosaminoglycan chains
Summary
Of Bio-Organic Chemistry, Utrecht University, Utrecht, The cartilage chondroitin 6-sulfate proteoglycans (11).These linkages, which werperepared using chondroitinase ABC, had the conventional core hexasaccharide structure in common: A4,5GlcA1@(1-3)Ga1NAc@(1-4)G1cA@(1-3)Ga1@(1-3)Ga1@(1-4). Matography, yielding [123,18,108], and[33] nmol (as A4,5-GlcA), In the present study we will present the di- and trisulfated respectively, per 100mg of the peptidoglycans containing 1.84 compounds derived from the linkage region of shark cartilage @molof Ser. In addition fraction 14 was separated using a chondroitin 6-sulfate proteoglycans. HPLC-Fractionation of the linkage oligosaccharidesand analysis of the chondroitinase ACII digests of the isolated oligosaccharides were carried out by HPLC (11).Chromatography was performed on a 4.6 X 250-mm polyamine-bound silica PA03 column (YMC Co., Kyoto) in an LC6A HPLC system (Shimadzu Corp., Kyoto) using a linear gradient from 16 to 530 mM NaH2P04over a 60-min period a t further separation. Fraction 10 (0.4 nmol) yielded two unsaturated disaccharides, ADi-OS (0.20 nmol) and ADi-6S (0.17 nmol), and two
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