Preparation of a series of sulfated tetrasaccharides from shark cartilage chondroitin sulfate D using testicular hyaluronidase and structure determination by 500 MHz1H NMR spectroscopy |
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Authors: | Kazuyuki Sugahara Yukako Tanaka Shuhei Yamada |
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Institution: | (1) Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, 658 Kobe, Japan |
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Abstract: | Six tetrasaccharide fractions were isolated from shark cartilage chondroitin sulfate D by gel filtration chromatography followed by HPLC on an amine-bound silica column after exhaustive digestion with testicular hyaluronidase. Their structures were determined unambiguously by one- and two-dimensional 500 MHz1H NMR spectroscopy in conjunction with HPLC analysis of chondroitinase AC-II digests of the tetrasaccharides. One fraction was found to contain two tetrasaccharide components. All the seven tetrasaccharides shared the common core structure GlcA1-3GalNAc1-4GlcA1-3GalNAc with various sulfation profiles. Four were disulfated comprising of two monosulfated disaccharide units GlcA1-3GalNAc(4-sulfate) and/or GlcA1-3GalNAc(6-sulfate), whereas the other three were hitherto unreported trisulfated tetrasaccharides containing a disulfated disaccharide unit GlcA(2-sulfate)1-3GalNAc(6-sulfate) and a monosulfated disaccharide unit GlcA1-3GalNAc(4-or 6-sulfate). These sulfated tetrasaccharides were demonstrated to serve as appropriate acceptor substrates for serum -N-acetylgalactosaminyltransferase, indicating their usefulness as authentic oligosaccharide substrates or probes for the glycobiology of sulfated glycosaminoglycans.Abbreviations NFU
National formulary unit
- COSY
correlation spectroscopy
- HOHAHA
homonuclear Hartmann-Hahn
- 1D or 2D
one- or two-dimensional
- IdoA
l-iduronic acid
- GlcA
d-gluco-4-enepyranosyluronic acid
- Di-0S
GlcA1-3GalNAc
- Di-4S
GlcA1-3GalNAc(4-sulfate)
- Di-4S
GlcA1-3GalNAc(4-sulfate)
- Di-6S
GlcA1-3GalNAc(6-sulfate)
- Di-6S
GlcA1-3GalNAc(6-sulfate)
- Di-diS
d
GlcA(2-sulfate)1-3GalNAc(6-sulfate)
- Di-diSE
GlcA1-3GalNAc(4, 6-disulfate)
- U
G, U, 2S, 4S, and 6S represent GlcA, GalNAc, GlcA, 2-O-sulfate, 4-O-sulfate, and 6-O-sulfate, respectively |
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Keywords: | chondroitin sulfate sulfated tetrasaccharides 500 MHz1H NMR |
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