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Preparation of a series of sulfated tetrasaccharides from shark cartilage chondroitin sulfate D using testicular hyaluronidase and structure determination by 500 MHz1H NMR spectroscopy

  • Glycoconjugate Journal
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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 GlcAβ1-3GalNAcβ1-4GlcAβ1-3GalNAc with various sulfation profiles. Four were disulfated comprising of two monosulfated disaccharide units GlcAβ1-3GalNAc(4-sulfate) and/or GlcAβ1-3GalNAc(6-sulfate), whereas the other three were hitherto unreported trisulfated tetrasaccharides containing a disulfated disaccharide unit GlcA(2-sulfate)β1-3GalNAc(6-sulfate) and a monosulfated disaccharide unit GlcAβ1-3GalNAc(4-or 6-sulfate). These sulfated tetrasaccharides were demonstrated to serve as appropriate acceptor substrates for serum α-N-acetylgalactosaminyltransferase, indicating their usefulness as authentic oligosaccharide substrates or probes for the glycobiology of sulfated glycosaminoglycans.

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Abbreviations

NFU:

National formulary unit

COSY:

correlation spectroscopy

HOHAHA:

homonuclear Hartmann-Hahn

1D or 2D:

one- or two-dimensional

IdoA:

l-iduronic acid

ΔGlcA:

d-gluco-4-enepyranosyluronic acid

ΔDi-0S:

ΔGlcAβ1-3GalNAc

Di-4S:

GlcAβ1-3GalNAc(4-sulfate)

ΔDi-4S:

ΔGlcAβ1-3GalNAc(4-sulfate)

Di-6S:

GlcAβ1-3GalNAc(6-sulfate)

ΔDi-6S:

ΔGlcAβ1-3GalNAc(6-sulfate)

ΔDi-diS d :

ΔGlcAβ(2-sulfate)α1-3GalNAc(6-sulfate)

ΔDi-diSE :

ΔGlcAβ1-3GalNAc(4, 6-disulfate)

ΔU:

G, U, 2S, 4S, and 6S represent ΔGlcA, GalNAc, GlcA, 2-O-sulfate, 4-O-sulfate, and 6-O-sulfate, respectively

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Authors and Affiliations

  1. Department of Biochemistry, Kobe Pharmaceutical University, Higashinada-ku, 658, Kobe, Japan

    Kazuyuki Sugahara, Yukako Tanaka & Shuhei Yamada

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  1. Kazuyuki Sugahara
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  2. Yukako Tanaka
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  3. Shuhei Yamada
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Sugahara, K., Tanaka, Y. & Yamada, S. Preparation of a series of sulfated tetrasaccharides from shark cartilage chondroitin sulfate D using testicular hyaluronidase and structure determination by 500 MHz1H NMR spectroscopy. Glycoconjugate J 13, 609–619 (1996). https://doi.org/10.1007/BF00731449

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  • DOI: https://doi.org/10.1007/BF00731449

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