Institute of Biological Chemistry, Academia Sinica, No. 128, Academia Road Section 2, Nan-Kang, Taipei, 11529, Taiwan.
Chem Asian J. 2013 Jul;8(7):1536-50. doi: 10.1002/asia.201201204. Epub 2013 May 2.
We have developed an expeditious procedure to yield large amounts of orthogonally protected Gal-β1,3/4-GlcNAc, which allowed for the systematic introduction of a sulfate group onto the C3/C6 positions of Gal and/or the C6 position of GlcNAc. In particular, the disaccharide precursors were prepared in five or six steps and high overall yield from para-tolyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-galactopyranoside. After deprotection and sulfation steps, the final products were characterized by using several NMR methods to unambiguously confirm the location of each introduced sulfate group and they were examined for their binding specificity of human galectin-1 and galectin-8.
我们开发了一种快速的方法来大量获得正交保护的 Gal-β1,3/4-GlcNAc，这使得我们能够系统地在 Gal 的 C3/C6 位置和/或 GlcNAc 的 C6 位置引入硫酸基团。特别是，二糖前体可以从对甲苯基-6-O-叔丁基二苯基甲硅基-1-硫代-β-D-半乳糖吡喃糖苷出发，经过五或六步反应以较高的总收率得到。经过脱保护和硫酸化步骤后，使用几种 NMR 方法对最终产物进行了表征，以明确确认每个引入的硫酸基团的位置，并对它们与人类半乳糖凝集素-1 和半乳糖凝集素-8 的结合特异性进行了研究。
