FLUORINATED CARBOHYDRATES AS POTENTIAL PLASMA-MEMBRANE MODIFIERS - SYNTHESIS OF 4-FLUORO AND 6-FLUORO DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-HEXOPYRANOSES
FLUORINATED CARBOHYDRATES AS POTENTIAL PLASMA-MEMBRANE MODIFIERS - SYNTHESIS OF 4-FLUORO AND 6-FLUORO DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-HEXOPYRANOSES
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DOI：
10.1016/0008-6215(90)84293-4
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发表时间：
1990-05-01
影响因子：
3.1
通讯作者：
KORYTNYK, W
中科院分区：
文献类型：
--
作者：
SHARMA, M;BERNACKI, RJ;KORYTNYK, W
2-Amino-2,4-dideoxy-4-fluoro- and 2-amino-2,4,6-trideoxy-4,6-difluoro-D-galactose, and 2-amino-2,4-dideoxy-4-fluoro- and 2-amino-4-deoxy-4,4-difluoro-D-xylo-hexose were synthesized, as potential modifiers of tumor cell-surface glycoconjugate, from benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-di-O-mesyl-.alpha.-D-glucopyranoside and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-mesyl-.alpha.-D-glucopyranoside, which were converted into the corresponding 4,6-difluoro-2,4-6-trideoxy and 2,4-dideoxy-4-fluoro derivatives. Benzyl 2-acetamido-2-deoxy-4-O-mesyl-.alpha.-D-galactopyranoside and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-.alpha.-D-xylo-hoxo-4-ulopyranoside were treated with diethylaminosulfur trifluoride to give 2-amino-2,4-dideoxy-4-fluoro-D-glucose and 2-amino-2,4-dideoxy-4,4-difluoro-D-xylo-hexose derivatives, respectively, to give after deprotection the target compounds. Several of the peracetylated sugar derivatives inhibited L1210 tumor-cell growth in vitro at concentrations of 1-5 10-5 M. The peracetylated derivative of 2-amino-2,4-dideoxy-4-fluoro-D-galactose inhibited protein and glycoconjugate biosynthesis, and also exhibited antitumor activity in mice with L1210 leukemia.
