Syntheses of the 4-nitrophenyl glycosides of hyalobiuronic acid and chondrosine.
4-Nitrophenyl [sodium beta-D-glucopyranosyluronate]-(1-->3)-2-acetamido-2-deoxy-beta-D-glucopyranoside (1) and 4-nitrophenyl [sodium beta-D-glucopyranosyluronate]-(1-->3)-2-acetamido-2-deoxy-beta-D-galactopyranoside (2) were prepared from the zwitterions hyalobiuronic acid [beta-D-glucopyranuronic acid-(1-->3)-2-amino-2-deoxy-D-glucopyranose] and chondrosine [beta-D-glucopyranuronic acid-(1-->3)-2-amino-2-deoxy-D-galactopyranose], respectively. Compounds 1 and 2 were not hydrolysed by bovine testicular hyaluronidase.
Watt
Derek K
DK
Industrial Research Ltd., Gracefield Road, PO Box 31-310, Lower Hutt, New Zealand. d.watt@irl.cri.nz
Clinch
Keith
K
Slim
George C
GC
D000818:Animals; D002417:Cattle; D004187:Disaccharides / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D006820:Hyaluronic Acid / Q000737:chemistry*; D006821:Hyaluronoglucosaminidase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009596:Nitrophenols / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D014574:Uronic Acids / Q000737:chemistry*
D004187:Disaccharides; D006027:Glycosides; D009596:Nitrophenols; D014574:Uronic Acids; C024719:4-nitrophenyl; C474983:hyalobiuronic acid; C068966:chondrosine; D006820:Hyaluronic Acid; D006821:Hyaluronoglucosaminidase