TY - JOUR
T1 - A facile synthesis of bifunctional phospholipids for biomimetic membrane engineering
AU - Sun, Xue
AU - Cui, Wanxing
AU - Kai, Toshistugu
AU - Chaikof, Elliot L.
PY - 2004/12/13
Y1 - 2004/12/13
N2 - We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1- dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. Graphical Abstract © 2004 Elsevier Ltd. All rights reserved.
AB - We report a facile synthesis of bifunctional phospholipid conjugates by acylation of N-protected lyso-phosphatidylethanolamine with 12-acryloxy-1- dodecanoic acid and followed with deprotection and conjugation with biotin, FITC, Texas Red, or EMC groups. The lipid conjugates can be used to generate a multifunctional substrate-supported phospholipid membrane via bioconjugation reaction to biotin or covalent attachment to EMC at their hydrophilic terminus. In addition, conjugation to fluorophores, FITC or Texas Red, provides a convenient mechanism to monitor lipid membrane formation and stability. Significantly, in situ photopolymerization of the acrylate group at the end of one of two hydrophobic alkyl chains stabilizes the phospholipid membrane. Graphical Abstract © 2004 Elsevier Ltd. All rights reserved.
KW - Biotin
KW - Fluorescent
KW - Membrane-mimetic
KW - Polymerizable phospholipid
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U2 - 10.1016/j.tet.2004.09.110
DO - 10.1016/j.tet.2004.09.110
M3 - Article
SN - 0040-4020
VL - 60
SP - 11765
EP - 11770
JO - Tetrahedron
JF - Tetrahedron
IS - 51
ER -