Ako Takuro, Daikoku Shusaku, Ohtsuka Isao, Kato Rumiko, Kanie Osamu
Mitsubishi Kagaku Institute of Life Sciences, 11 Minamiooya, Machida-shi, Tokyo 194-8511, Japan.
Chem Asian J. 2006 Dec 18;1(6):798-813. doi: 10.1002/asia.200600210.
A new, efficient synthesis of oligosaccharides, which involves solid-phase reactions without mixing in combination with an orthogonal-glycosylation strategy, is described. Despite a great deal of biological interest, the combinatorial chemistry of oligosaccharides is an extremely difficult subject. The problems include 1) lengthy synthetic protocols required for the synthesis and 2) the variety of glycosylation conditions necessary for individual reactions. These issues were addressed and solved by using the orthogonal-coupling protocol and the application of a temperature gradient to provide appropriate conditions for individual reactions. Furthermore, we succeeded in carrying out solid-phase reactions with neither mechanical mixing nor flow. In this report, the synthesis of a series of trisaccharides, namely, alpha/beta-L-Fuc-(1-->6)-alpha/beta-D-Gal-(1-->2/3/4/6)-alpha/beta-D-Glc-octyl, is reported to demonstrate the eligibility of the synthetic method in combinatorial chemistry.
本文描述了一种新的、高效的寡糖合成方法，该方法涉及不进行混合的固相反应，并结合了正交糖基化策略。尽管寡糖具有极大的生物学研究价值，但其组合化学却是一个极其困难的课题。这些问题包括：1）合成所需的冗长合成方案；2）各个反应所需的多种糖基化条件。通过使用正交偶联方案和应用温度梯度为各个反应提供合适的条件，这些问题得以解决。此外，我们成功地在既不进行机械混合也不采用流动的情况下进行了固相反应。在本报告中，我们报道了一系列三糖，即α/β-L-岩藻糖-(1→6)-α/β-D-半乳糖-(1→2/3/4/6)-α/β-D-葡萄糖-辛酯的合成，以证明该合成方法在组合化学中的适用性。
