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J Biol Chem, Vol. 273, Issue 6, 3296-3307, February 6, 1998
,,
From the A mouse brain chondroitin sulfate (CS)
proteoglycan, DSD-1-PG, bears the DSD-1 epitope and has neurite
outgrowth promoting properties. Shark cartilage CS-C inhibits the
interactions between the DSD-1-specific monoclonal antibody 473HD and
the CS chains of the DSD-1-PG, which is expressed on the mouse glial
cells (Faissner, A., Clement, A., Lochter, A., Streit, A., Mandl, C.,
and Schachner, M. (1994) J. Cell Biol. 126, 783-799). On
the other hand, several hexasaccharides isolated from commercial shark
cartilage CS-D, which contains a higher proportion of characteristic D
units (GlcUA(2-sulfate) Department of Biochemistry, Kobe
Pharmaceutical University, Higashinada-ku, Kobe 658, Japan and the
§ Department of Neurobiology, University of Heidelberg,
D-69120 Heidelberg, Germany
1-3GalNAc(6-sulfate)) as compared with CS-C,
has the A-D tetrasaccharide sequence composed of an A disaccharide
unit (GlcUA1-3GalNAc(4-sulfate)) and a D disaccharide unit
(Nadanaka, S. and Sugahara, K. (1997) Glycobiology 7, 253-263). In this study, the biological activities and the structure
of shark cartilage CS-D were investigated. CS-D inhibited the
interactions between monoclonal antibody 473HD and DSD-1-PG and also
promoted neurite outgrowth of embryonic day 18 hippocampal neurons.
Eight octasaccharide fractions were isolated from CS-D after partial
digestion with bacterial chondroitinase ABC by means of gel filtration
chromatography and anion-exchange high performance liquid
chromotography to investigate the frequency and the arrangement of the A-D tetrasaccharide unit in the polymer sequence. Structural analysis performed by a combination of enzymatic digestions with 500-MHz 1H NMR spectroscopy demonstrated that the isolated
octasaccharides shared the common core structure
HexA
1-3GalNAc1-4(GlcUA1-3GalNAc)3 with
four, five, and six sulfate esters at various hydroxyl groups in
different combinations. In the structure, HexA and GlcUA
represent 4-deoxy--L-threo-hex-4-enepyranosyluronic
acid and glucuronic acid, respectively. No D-D tetrasaccharide sequence
was found, and discrete D disaccharide units were demonstrated
exclusively as A-D tetrasaccharide units in either an A-D-A or an A-D-C
hexasaccharide sequence in the five octasaccharides that represented
about 5.0% (w/w) of the starting polysaccharides (C denotes the
disaccharide GlcUA1-3GalNAc(6-sulfate)). It remains to be
determined whether such characteristic hexasaccharide sequences present
in shark cartilage CS-D serve as functional domain structures
recognized by some protein ligands.
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