Phosphonate lipid tubules II.
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.
Thomas
Britt N
BN
Department of Chemistry, Louisiana State University, Baton Rouge, Louisiana 70803, USA.
Lindemann
Christopher M
CM
Corcoran
Robert C
RC
Cotant
Casey L
CL
Kirsch
Janet E
JE
Persichini
Phillip J
PJ
D053280:Diynes; D008567:Membranes, Artificial; D018625:Microscopy, Atomic Force; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry*; D010713:Phosphatidylcholines / Q000138:chemical synthesis / Q000737:chemistry*; D012542:Scattering, Radiation; D014965:X-Rays
D053280:Diynes; D008567:Membranes, Artificial; D063065:Organophosphonates; D010713:Phosphatidylcholines; C053923:1,2-bis(10,12-tricosadiynoyl)phosphatidylcholine