Synthesis of 9-O-acyl- and 4-O-acetyl-sialic acids
β Scribed by Haruo Ogura; Kimio Furuhata; Shingo Sato; Katsuko Anazawa; Masayoshi Itoh; Yoshiyasu Shitori
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- English
- Weight
- 644 KB
- Volume
- 167
- Category
- Article
- ISSN
- 0008-6215
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β¦ Synopsis
Various 9-0-acyl derivatives of N-acetyl-and N-glycoloyl-neuraminic acid, and O-(5-acetamido-3,5-dideoxy-D-glycero-c-and -/3-D-gulucto-2-nonulopyranosylonic acid)-(2~6)-O-~-D-galactopyranosyl-(1~4)-D-glucopyranose were regioselectively synthesized by use of ortho esters. In addition, 5-acetamido-4-O-acetyl-D-glycero-D-galacfo-2nonulopyranosonic acid was prepared starting from the benzyl and methyl esters of N-acetylneuraminic acid. *Studies on sialic acids. VI.
π SIMILAR VOLUMES
4-O-Acetyl sialic acid derivative could be easily prepared from the hydrolysis of 1 by lipase OF via the migration of acetyl groups.
## Abstract Two new fluorescent regioselective __O__βacetylated __N__βacetylneuraminic acid (Neu5Ac) thioketosides, 2Ξ±β[4β(dansylamino)phenylthio]β7,8,9βtriβ__O__βacetylβ__N__βacetylneuraminic acid {2Ξ±β[4β(dansylamino)phenylthio]βNeu5,7,8,9Ac~4~} (3) and 2Ξ±β[4β(dansylamino)phenylthio]β4β__O__βacety
The presence of mono-, di-, and tri-O-acetylated sialic acids on human cells was demonstrated by using radiochromatographic and chemical techniques. Human melanoma cells and fresh colon tissue were biosynthetically labeled with 6- (3H) glucosamine. Radiolabeled sialic acids were hydrolytically remov