Comber R N, Friedrich J D, Dunshee D A, Petty S L, Secrist J A
Organic Chemistry Department, Southern Research Institute, Birmingham, Alabama 35255-5305.
Carbohydr Res. 1994 Sep 15;262(2):245-55. doi: 10.1016/0008-6215(94)84182-9.
The syntheses of several alpha-linked thioglycosidic disaccharides are described, including thiokojibiose octaacetate (1), thionigerose (2), and thioisomaltose (3). The title compounds were synthesized by coupling 2,3,4,6-tetra-O-acetyl-1.5-acetyl-1-thio-alpha-D-glucopyranose (4) with either 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethylsulfonyl-beta-D-manno pyr anose (7), 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-++ +allofuranose (15), or methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-alpha-D-glucopyranoside (17), respectively. Thiokojibiose octaacetate in turn was converted to 3,4,6-tri-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-2 -thio-alpha-D-glucopyranosyl bromide (9), which was used to obtain several related disaccharides and one trisaccharide. All of the compounds, including thiomaltose and thiotrehalose, which were resynthesized by known methods, were tested for their anti-HIV activity in either CEM or MT-2 cells. Anti-HIV activity was noted only with thiokojibiose octaacetate and its 1-thio analogue (14), which had IC50 values of 51 and 48 micrograms/mL in CEM cells, respectively.
描述了几种α-连接的硫代糖苷二糖的合成，包括硫代 kojibiose 八乙酸酯（1）、硫代黑曲霉糖（2）和硫代异麦芽糖（3）。通过将 2,3,4,6-四-O-乙酰基-1,5-乙酰基-1-硫代-α-D-吡喃葡萄糖（4）分别与 1,3,4,6-四-O-乙酰基-2-O-三氟甲基磺酰基-β-D-甘露吡喃糖（7）、1,2:5,6-二-O-异亚丙基-3-O-三氟甲基磺酰基-α-D-呋喃葡萄糖（15）或甲基 2,3,4-三-O-乙酰基-6-脱氧-6-碘-α-D-吡喃葡萄糖苷（17）偶联来合成标题化合物。硫代 kojibiose 八乙酸酯又被转化为 3,4,6-三-O-乙酰基-2-S-(2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖基)-2-硫代-α-D-吡喃葡萄糖基溴（9），其用于获得几种相关的二糖和一种三糖。所有化合物，包括通过已知方法重新合成的硫代麦芽糖和硫代海藻糖，都在 CEM 或 MT-2 细胞中测试了它们的抗 HIV 活性。仅硫代 kojibiose 八乙酸酯及其 1-硫代类似物（14）具有抗 HIV 活性，它们在 CEM 细胞中的 IC50 值分别为 51 和 48 微克/毫升。
