ISSN:
1573-4986
Keywords:
chondroitin sulfate H
;
dermatan sulfate
;
glycosaminoglycan
;
sulfated oligosaccharides
;
CS, chondroitin sulfate
;
DS, dermatan sulfate
;
GalNAc, N-acetyl-D-galactosamine
;
GlcA, D-glucuronic acid
;
IdoA, L-iduronic acid
;
HexA, hexuronic acid
;
HexNAc, N-acetyl-D-hexosamine
;
ΔHexA or Δ4,5HexA, 4-deoxy-α-threo-hex-4-enepyranosyluronic acid
;
HCII, heparin cofactor II
;
COSY, correlation spectroscopy
;
1 or 2D, one- or two-dimensional
;
ΔDi-0S, Δ4,5HexAα1-3GalNAc
;
ΔDi-4S, Δ4,5HexAα1-3GalNAc(4-O-sulfate)
;
ΔDi-6S, Δ4,5HexAα1-3GalNAc(6-O-sulfate)
;
ΔDi-diSB, Δ4,5HexA(2-Osulfate)α1-3GalNac(4-O-sulfate)
;
ΔDi-diSD, Δ4,5HexA(2-O-sulfate)α1-3GalNAc(6-O-sulfate)
;
ΔDi-diSE, Δ4,5HexAα1-3GalNac(4,6-O-disulfate)
;
ΔDi-triS, Δ4,5HexA(2-O-sulfate)α1-3GalNAc(4,6-O-disulfate)
;
Δhexuronate-2-, CS-4- or CS-6-sulfatase stands for Δ4,5hexuronate-2-O-, chondro-4-O- or -6-O-sulfatase, respectively
;
ΔU, G, U, 2S, 4S and 6S denote Δ4,5HexA, GalNAc, IdoA, 2-O-, 4-O- and 6-O-sulfate, respectively
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Oversulfated chondroitin sulfate H (CS-H) isolated from hagfish notochord is a unique dermatan sulfate consisting mainly of IdoAα1-3GalNAc(4S,6S), where IdoA, GalNAc, 4S and 6S represent L-iduronic acid, N-acetyl-D-galactosamine, 4-O-sulfate and 6-O-sulfate, respectively. Several tetra- and hexasaccharide fractions were isolated from CS-H after partial digestion with bacterial chondroitinase B to investigate the sequential arrangement of the IdoAα1-3GalNAc(4S,6S) unit in the CS-H polysaccharide. A structural analysis of the isolated oligosaccharides by enzymatic digestions, mass spectrometry and 1H NMR spectroscopy demostrated that the major tetrasaccharides shared the common disulfated core structure Δ4,5HexAα1-3GalNAc(4S)β1-4IdoAα1-3GalNAc(4S) with 0 ∼ 3 additional O-sulfate groups, where Δ4,5HexA represents 4-deoxy-α-L-threo-hex-4-enepyranosyluronic acid. The major hexasaccharides shared the common trisulfated core structure Δ4,5HexAα1-3GalNAc(4S)β1-4IdoAα1-3GalNAc(4S)β1-4IdoAα1-3GalNAc(4S) with 1 ∼ 4 additional O-sulfate groups. Some extra sulfate groups in both tetra- and hexasaccharides were located at the C-2 position of a Δ4,5HexA or an internal IdoA residue, or C-6 position of 4-O-sulfated GalNAc residues, forming the unique disulfated or trisulfated disaccharide units, IdoA (2S)-GalNAc(4S), IdoA-GalNAc(4S,6S) and IdoA (2S)-GalNAc(4S,6S), where 2S represents 2-O-sulfate. Of the demonstrated sequences, five tetra- and four hexasaccharide sequences containing these units were novel.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1007022229813
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