Conformationally supple glucose monomers enable synthesis of the smallest cyclodextrins
Conformationally supple glucose monomers enable synthesis of the smallest cyclodextrins
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DOI：
10.1126/science.aaw3053
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发表时间：
2019-05-17
期刊：
影响因子：
56.9
通讯作者：
Yamada, Hidetoshi
中科院分区：
文献类型：
--
作者：
Ikuta, Daiki;Hirata, Yasuaki;Yamada, Hidetoshi
环糊精（CDs）是α -1,4- d -葡萄糖吡喃苷的环状低聚物，主要是六聚体到八聚体。cd的中心空腔可以保留小分子，从而实现多种应用。最小的成员CD3和CD4的环尺寸太小，无法形成最稳定的葡萄糖醛酸构象，也无法合成。在这项研究中，我们提出了化学合成CD3和CD4的方法。成功合成的主要因素是在富赤道和富轴向形式之间形成了一个构象平衡的葡萄糖吡喃糖环。这种柔韧性是由葡萄糖的0-3和0-6之间的桥梁赋予的，这使得在合成环三聚体和四聚体时能够产生理想的，尽管变形的构象。
Cyclodextrins (CDs) are cyclic oligomers of alpha-1,4-D-glucopyranoside and are known mainly as hexamers to octamers. The central cavities of CDs can retain small molecules, enabling diverse applications. The smallest members, CD3 and CD4, have ring sizes too small to permit the most stable conformations of glucopyranose and have not been accessible synthetically. In this study, we present methods to chemically synthesize both CD3 and CD4. The main factor in the successful synthesis is the creation of a glucopyranose ring conformationally counterbalanced between equatorial-and axial-rich forms. This suppleness is imparted by a bridge between 0-3 and 0-6 of glucose, which enables the generation of desirable, albeit deformed, conformers when synthesizing the cyclic trimer and tetramer.