Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

Toshitsugu Kai; Xue Sun; Keith M. Faucher; Robert P. Apkarian; Elliot L. Chaikof

doi:10.1021/jo048167o

Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

Toshitsugu Kai
, Xue Sun
, Keith M. Faucher
, Robert P. Apkarian
, Elliot L. Chaikof

Chemistry

Emory University
Georgia Institute of Technology

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

(Chemical Equation Presented) A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures. © 2005 American Chemical Society.

Original language	English
Pages (from-to)	2606-2615
Number of pages	10
Journal	Journal of Organic Chemistry
Volume	70
Issue number	7
DOIs	https://doi.org/10.1021/jo048167o
State	Published - Apr 1 2005

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title = "Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles",

abstract = "(Chemical Equation Presented) A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures. {\textcopyright} 2005 American Chemical Society.",

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T1 - Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

AU - Kai, Toshitsugu

AU - Sun, Xue

AU - Faucher, Keith M.

AU - Apkarian, Robert P.

AU - Chaikof, Elliot L.

PY - 2005/4/1

Y1 - 2005/4/1

N2 - (Chemical Equation Presented) A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures. © 2005 American Chemical Society.

AB - (Chemical Equation Presented) A synthetic route was devised for the generation of asymmetric lipid bolaamphiphiles through the sequential esterification of an alkyldioic acid, bearing distinct terminal protecting groups, with propanylamine and lyso-phosphatidylcholine headgroups. Bolaamphiphile self-assembly was investigated in solvent mixes of varying polarity by nuclear magnetic resonance (NMR) and Fourier transform-infrared (FT-IR) spectroscopy, as well as in water by cryo-high-resolution scanning electron microscopy (cryo-HRSEM). We anticipate that asymmetric lipid bolaamphiphiles will provide facile building blocks for engineering a variety of unique membrane-mimetic structures. © 2005 American Chemical Society.

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Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

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