由不对称双亲媒性分子制成的单层脂质膜结构的多态性。

Polymorphism of monolayer lipid membrane structures made from unsymmetrical bolaamphiphiles.

作者信息

Masuda Mitsutoshi, Yoza Kenji, Shimizu Toshimi

机构信息

Nanoarchitectonics Research Center (NARC), National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, 1-1-1 Higashi, Tsukuba, Ibaraki 305-8565, Japan.

出版信息

Carbohydr Res. 2005 Nov 21;340(16):2502-9. doi: 10.1016/j.carres.2005.08.005. Epub 2005 Oct 5.

DOI:10.1016/j.carres.2005.08.005

PMID:16168972

Abstract

The crystal structures of synthetic unsymmetrical 1-glucosamide- and 1-galactosamide bolaamphiphiles, 13-[(beta-d-glucopyranosyl)carbamoyl]tridecanoic acid (1) and 15-[(beta-d-galactopyranosyl)carbamoyl]pentadecanoic acid (2), respectively, were elucidated by single-crystal X-ray analysis. The space group for 1 is P2(1), Z=2 with cell dimensions: a=8.6816(9), b=4.8578(5), c=26.250(3)A, beta=91.460(2) degrees ; that for 2P2(1), Z=2 with cell dimensions: a=4.90(1), b=40.139(1), 6.289(1)A, beta=106.48(1) degrees . The glucopyranosyl and galactopyranosyl rings in 1 and 2, respectively, take a (4)C(1) chair conformation. In the crystal lattice, the 1-glucosamide 1 forms a symmetrical monolayer lipid membrane (MLM) structure in which the molecules are packed in an antiparallel fashion, while 1-galactosamide 2 has an unsymmetrical MLM with parallel molecular packing. The stereochemistry of the sugar hydroxy group proved to affect their hydrogen-bonding networks and induce the polymorphism of the MLM.

摘要

通过单晶X射线分析分别阐明了合成的不对称1-葡糖酰胺和1-半乳糖酰胺两亲分子，即13-[(β-D-吡喃葡萄糖基)氨基甲酰基]十三烷酸(1)和15-[(β-D-吡喃半乳糖基)氨基甲酰基]十五烷酸(2)的晶体结构。1的空间群为P2(1)，Z = 2，晶胞参数：a = 8.6816(9)，b = 4.8578(5)，c = 26.250(3)Å，β = 91.460(2)°；2的空间群为P2(1)，Z = 2，晶胞参数：a = 4.90(1)，b = 40.139(1)，c = 6.289(1)Å，β = 106.48(1)°。1和2中的吡喃葡萄糖基环和吡喃半乳糖基环分别采取(4)C(1)椅式构象。在晶格中，1-葡糖酰胺1形成对称的单层脂质膜(MLM)结构，其中分子以反平行方式堆积，而1-半乳糖酰胺2具有分子平行堆积的不对称MLM。糖羟基的立体化学被证明会影响它们的氢键网络并诱导MLM的多晶型。