Synthesis of hyaluronic-acid-related oligosaccharides and analogues, as their 4-methoxyphenyl glycosides, having N-acetyl-beta-D-glucosamine at the reducing end.
To contribute to the possibilities to study the ability of oligosaccharide fragments of hyaluronic acid to induce angiogenesis, several hyaluronic-acid-related oligosaccharides and their 6-O-sulfated analogues were synthesised as their 4-methoxyphenyl glycosides having 2-acetamido-2-deoxy-D-glucopyranose at the reducing end. In all syntheses described, the D-glucopyranosyluronic acid residue was obtained by oxidation at C-6 of a corresponding D-glucopyranosyl residue after construction of the oligosaccharide backbone, using pyridinium dichromate and acetic anhydride.
Halkes
K M
KM
Bijvoet Center, Department of Bio-Organic Chemistry, Utrech University, The Netherlands.
Slaghek
T M
TM
Hyppönen
T K
TK
Kruiskamp
P H
PH
Ogawa
T
T
Kamerling
J P
JP
Vliegenthart
J F
JF
D000089:Acetic Anhydrides; D000117:Acetylglucosamine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006820:Hyaluronic Acid / Q000737:chemistry*; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011726:Pyridinium Compounds
D000089:Acetic Anhydrides; D006027:Glycosides; D007202:Indicators and Reagents; D009844:Oligosaccharides; D011726:Pyridinium Compounds; C061685:pyridinium dichromate; C031800:acetic anhydride; D006820:Hyaluronic Acid; D000117:Acetylglucosamine