Molecular structure of glucopyranosylamide lipid and nanotube morphology
Molecular structure of glucopyranosylamide lipid and nanotube morphology
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DOI：
10.1021/la047765v
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发表时间：
2005-01-18
期刊：
影响因子：
3.9
通讯作者：
Shimizu, T
中科院分区：
文献类型：
--
作者：
Kamiya, S;Minamikawa, H;Shimizu, T
本文合成了一系列吡喃葡萄糖酰胺类脂质，N-（X-十八烯酰基）-β-D-吡喃葡萄糖胺[X = 13-cis（1），11-cis（2），9-cis（3），6-cis（4），9-cis，12-cis（5）]及其饱和同系物N-十八烯酰基-β-D-吡喃葡萄糖胺（6），它们在C18烃链中的顺式双键位置不同。用扫描电子显微镜研究了顺式双键位置对各糖基手性自组装的影响。透射电子显微镜，X射线，衍射。UV和圆二色性（CD）。观察到11-顺式衍生物2在水中自组装以形成具有约200-nm外径的均匀中空圆柱体结构，产率>98%。从2获得的纳米管显示出最窄的外径分布，并且还在234-236 nm附近产生负CD带，显示出所研究的糖脂中最大的CD强度。因此，我们发现顺式双键的位置显著影响自组装纳米管结构的外径均匀性以及生长行为。不饱和糖脂的可能弯曲结构驱动的手性分子堆积在通过分子自组装确定管状形态中起着关键作用。
A series of glucopyranosylamide lipids, N-(X-octadecenoyl)-beta-D-glucopyranosylamine [X = 13-cis (1), 11-cis (2), 9-cis (3), 6-cis (4), and 9-cis,12-cis (5)] and their saturated homologue N-octadecanoyl-beta-D-glucopyranosylamine (6), which differ in the position of a cis double bond in the C18 hydrocarbon chains, have been synthesized. The effect of the cis double bond position on the chiral self-assembly of each glycohpid has been examined by scanning electron microscopy. transmission electron microscopy, X-ray, diffraction. UV, and circular dichroism (CD). The 11-cis derivative 2 was observed to self-assemble in water to form a uniform hollow cylinder structure with about 200-nm outer diameters in >98% yields. The obtained nanotubes from 2 showed the narrowest distribution of outer diameters mid also gave a negative CD band around 234-236 nm, showing the largest CD intensity among the glycolipids investigated. Thus, we found that the position of a cis double bond significantly influences the homogeneity of the outer diameters as well as growth behavior of the self-assembled nanotube structures. Chiral molecular packing driven by a possible bending structure of the unsaturated glycolipids is playing a critical role in determining tubular morphology through molecular self-assembly.