STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .24. SYNTHESIS OF THE ALPHA-METHYLKETOSIDE OF 8-OXO-N-ACETYLNEURAMINIC ACID AND RELATED DERIVATIVES

被引:3
作者
HARTMANN, M [1 ]
ZBIRAL, E [1 ]
机构
[1] UNIV VIENNA,INST ORGAN CHEM,A-1090 VIENNA,AUSTRIA
来源
MONATSHEFTE FUR CHEMIE | 1991年 / 122卷 / 11期
关键词
SIALIC ACIDS; KETO-SUGARS; SYNTHESIS OF A METHYL GLYCOSIDE;
D O I
10.1007/BF00823430
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis of the sodium 5-acetamido-2,3,5-trideoxy-2,3 didehydro-D-galacto-2,8-nondiulopyranosidonate 8,8-dimethyl acetal (8) and of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonate 8,8 dimethyl acetal (11) as well as of the methyl-5-acetamido-3,5-dideoxy-alpha-D-galacto-2,8-nondiulopyranosidonic acid (12) is reported involving the easily accessible 8-oxo-derivative 5. Compounds 11 and 12, respectively, showed to have glycosidic bond with remarkable stability to acidic conditions.
引用
收藏
页码:995 / 1003
页数:9
相关论文
共 19 条
  • [1] BANDGAR BP, 1990, LIEBIGS ANN CHEM, P1185
  • [2] 4-METHYLUMBELLIFERYL 5-ACETAMIDO-3,4,5-TRIDEOXY-ALPHA-D-MANNO-2-NONULOPYRANOSIDONIC ACID - SYNTHESIS AND RESISTANCE TO BACTERIAL SIALIDASES
    BAUMBERGER, F
    VASELLA, A
    SCHAUER, R
    [J]. HELVETICA CHIMICA ACTA, 1986, 69 (08) : 1927 - 1935
  • [3] BEAU JM, 1979, 5TH P INT S GLYCOCON, P356
  • [4] STRUCTURE OF THE CATALYTIC AND ANTIGENIC SITES IN INFLUENZA-VIRUS NEURAMINIDASE
    COLMAN, PM
    VARGHESE, JN
    LAVER, WG
    [J]. NATURE, 1983, 303 (5912) : 41 - 44
  • [5] CZARNIECKI MF, 1977, J AM CHEM SOC, V99, P8273, DOI 10.1021/ja00467a025
  • [6] THE INTERACTION OF SUBSTRATE-RELATED KETALS WITH BACTERIAL AND VIRAL NEURAMINIDASES
    FLASHNER, M
    KESSLER, J
    TANENBAUM, SW
    [J]. ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1983, 221 (01) : 188 - 196
  • [7] STRUCTURAL VARIATIONS OF N-ACETYLNEURAMINIC ACID .12. A NEW USEFUL APPROACH TO 4-EPI-N-ACETYLNEURAMINIC AND 8-EPI-N-ACETYLNEURAMINIC ACID
    HARTMANN, M
    ZBIRAL, E
    [J]. MONATSHEFTE FUR CHEMIE, 1989, 120 (10): : 899 - 906
  • [8] HARTMANN M, 1991, LIEBIGS ANN CHEM, P795
  • [9] HARTMANN M, 1990, LIEBIGS ANN CHEM, P83
  • [10] HIGH-RESOLUTION H-1-NMR SPECTROSCOPY OF FREE AND GLYCOSIDICALLY LINKED O-ACETYLATED SIALIC ACIDS
    HAVERKAMP, J
    VANHALBEEK, H
    DORLAND, L
    VLIEGENTHART, JFG
    PFEIL, R
    SCHAUER, R
    [J]. EUROPEAN JOURNAL OF BIOCHEMISTRY, 1982, 122 (02): : 305 - 311