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.
引用
收藏
页码:1227 / 1233
页数:7
相关论文
共 29 条
  • [21] Theory of cylindrical tubules and helical ribbons of chiral lipid membranes
    Selinger, JV
    MacKintosh, FC
    Schnur, JM
    [J]. PHYSICAL REVIEW E, 1996, 53 (04) : 3804 - 3818
  • [22] Thermodynamics of phospholipid tubules in alcohol/water solutions
    Spector, MS
    Selinger, JV
    Schnur, JM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (36) : 8533 - 8539
  • [23] Left- and right-handed helical tubule intermediates from a pure chiral phospholipid
    Thomas, BN
    Lindemann, CM
    Clark, NA
    [J]. PHYSICAL REVIEW E, 1999, 59 (03): : 3040 - 3047
  • [24] LIPID TUBULE SELF-ASSEMBLY - LENGTH DEPENDENCE ON COOLING RATE THROUGH A FIRST-ORDER PHASE-TRANSITION
    THOMAS, BN
    SAFINYA, CR
    PLANO, RJ
    CLARK, NA
    [J]. SCIENCE, 1995, 267 (5204) : 1635 - 1638
  • [25] Phosphonate lipid tubules. 1
    Thomas, BN
    Corcoran, RC
    Cotant, CL
    Lindemann, CM
    Kirsch, JE
    Persichini, PJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (47) : 12178 - 12186
  • [26] THOMSON BM, 1992, CONTROL OF FAT AND LEAN DEPOSITION, P83
  • [27] FORMATION OF TUBULES BY A POLYMERIZABLE SURFACTANT
    YAGER, P
    SCHOEN, PE
    [J]. MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1984, 106 (3-4): : 371 - 381
  • [28] STRUCTURE OF LIPID TUBULES FORMED FROM A POLYMERIZABLE LECITHIN
    YAGER, P
    SCHOEN, PE
    DAVIES, C
    PRICE, R
    SINGH, A
    [J]. BIOPHYSICAL JOURNAL, 1985, 48 (06) : 899 - 906
  • [29] Self-assembly of helical ribbons
    Zastavker, YV
    Asherie, N
    Lomakin, A
    Pande, J
    Donovan, JM
    Schnur, JM
    Benedek, GB
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (14) : 7883 - 7887