Tejler Johan, Skogman Fredrik, Leffler Hakon, Nilsson Ulf J
Organic Chemistry, Lund University, PO Box 124, SE-221 00 Lund, Sweden.
Carbohydr Res. 2007 Sep 3;342(12-13):1869-75. doi: 10.1016/j.carres.2007.03.012. Epub 2007 Mar 14.
1H-[1,2,3]-Triazol-1-yl mannosides have been synthesized as inhibitors for the beta-galactoside-binding family of galectin proteins. Easier synthetic access to C1 in mannose, as compared to C3 in galactose, for attachment of affinity-enhancing triazoles rendered a synthetic advantage. The best mannose-derived inhibitor for galectin-9N, 4-benzylaminocarbonyl-1H-[1,2,3]-triazol-1-yl beta-D-mannopyranoside, had a Kd value of 540 microM, which compares favorably with its galactoside counterpart (Kd=670 microM) and with LacNAc (Kd=500 microM).
1H-[1,2,3] -三唑-1-基甘露糖苷已被合成作为半乳糖凝集素蛋白β-半乳糖苷结合家族的抑制剂。与半乳糖中的C3相比，甘露糖中C1更容易进行合成，便于连接增强亲和力的三唑，这带来了合成优势。半乳糖凝集素-9N的最佳甘露糖衍生抑制剂4-苄基氨基羰基-1H-[1,2,3] -三唑-1-基β-D-甘露吡喃糖苷的解离常数（Kd）值为540微摩尔，与对应的半乳糖苷（Kd = 670微摩尔）和乳糖-N-乙酰基神经氨酸（Kd = 500微摩尔）相比具有优势。
