Phosphonate lipid tubules II

被引:67
作者
Thomas, BN [1 ]
Lindemann, CM
Corcoran, RC
Cotant, CL
Kirsch, JE
Persichini, PJ
机构
[1] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
[2] Merck & Co Inc, Rahway, NJ 07065 USA
[3] Univ Wyoming, Dept Chem, Laramie, WY 82071 USA
关键词
D O I
10.1021/ja012137a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe a new chiral tubule-forming lipid in which the C-O-P phosphoryl linkage of the archetypal tubule-forming molecule, 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3-phosphocholine, "DC(8,9)PC", is replaced by a C-P linkage. Tubule formation with this phosphonate analogue proceeds under the same mild conditions as with DC(8,9)PC and produces similar yields, but synchrotron small-angle X-ray scattering, atomic force microscopy, and optical microscopy show the new tubules to have diameters 1.94 times as great, to be significantly shorter, and to be thinner-walled. A significant portion of the enantiomerically pure chiral phosphonate precipitate is in the form of stable open helices, and these helices are divided almost evenly between left- and right-handed members.
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页码:1227 / 1233
页数:7
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