SYNTHESIS OF 1-PALMITOYL-2-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE (PHPC)

被引：8
|
作者：
DUCLOS, RI
机构：
[1] Biophysics Department, Housman Medical Research Center, Boston University School of Medicine, Boston, MA 02118-2394
来源：
CHEMISTRY AND PHYSICS OF LIPIDS | 1993年 / 66卷 / 03期
关键词：
1-ACYL-2-ALKYL-SN-GLYCERO-3-PHOSPHOCHOLINE; 1-PALMITOYL-2-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE; PHPC; 1-ACETYL-2-HEXADECYL-SN-GLYCERO-3-PHOSPHOCHOLINE; AHPC; PALMITIC ANHYDRIDE;
D O I：
10.1016/0009-3084(93)90001-J
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A general method for the chirospecific synthesis of 1-acyl-2-alkyl-sn-glycero-3-phosphocholines is described. 1-Palmitoyl-2-hexadecyl-sn-glycero-3-phosphocholine (PHPC) was synthesized in 18% overall yield in ten steps via five new synthetic intermediates, and 1-acetyl-2-hexadecyl-sn-glycero-3-phosphocholine (AHPC) was also synthesized. 1-Acyl-2-alkyl-sn-glycero-3-phosphocholine which have not been found to exist in nature, are ether lipid analogs of 1,2-diacyl-sn-glycero-3-phosphocholines, which are important components of cell membranes. Biophysical studies of hydrated bilayers of PHPC will be of interest in probing the critical importance of the central region of these amphiphilic molecules to the molecular assemblies that are formed.
引用
收藏
页码：161 / 170
页数：10
相关论文
共 50 条
  • [31] 1-ALKYL-2-LYSO-SN-GLYCERO-3-PHOSPHOCHOLINE ACETYLTRANSFERASE
    LEE, TC
    VALLARI, DS
    SNYDER, F
    METHODS IN ENZYMOLOGY, 1992, 209 : 396 - 401
  • [32] Effect of Ca2+ ions on Bestrophin-1 interaction with 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine in surface films
    Mladenova, K.
    Petrova, S.
    Andreeva, T.
    Moskova-Doumanova, V.
    Lalchev, Z.
    Doumanov, J.
    FEBS JOURNAL, 2015, 282 : 319 - 320
  • [33] Differential Regulation of Endothelial Cell Permeability by High and Low Doses of Oxidized 1-Palmitoyl-2-Arachidonyl-sn-Glycero-3-Phosphocholine
    Starosta, Vitaliy
    Wu, Tinghuai
    Zimman, Alejandro
    Pham, Donald
    Tian, Xinyong
    Oskolkova, Olga
    Bochkov, Valery
    Berliner, Judith A.
    Birukova, Anna A.
    Birukov, Konstantin G.
    AMERICAN JOURNAL OF RESPIRATORY CELL AND MOLECULAR BIOLOGY, 2012, 46 (03) : 331 - 341
  • [34] Distributions of hydroperoxide positional isomers generated by oxidation of 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine in liposomes and in methanol solution
    Wang, XH
    Ushio, H
    Ohshima, T
    LIPIDS, 2003, 38 (01) : 65 - 72
  • [35] Computational investigation of lipid hydration water of Lα 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine at three hydration levels
    Pinnick, Eric R.
    Erramilli, Shyamsunder
    Wang, Feng
    MOLECULAR PHYSICS, 2010, 108 (15) : 2027 - 2036
  • [36] RELATIVE AMOUNTS OF 1-O-ALKYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE AND 1-ACYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE IN STIMULATED ENDOTHELIAL-CELLS
    WHATLEY, RE
    CLAY, KL
    CHILTON, FH
    TRIGGIANI, M
    ZIMMERMAN, GA
    MCINTYRE, TM
    PRESCOTT, SM
    PROSTAGLANDINS, 1992, 43 (01): : 21 - 29
  • [37] Analysis of Oxidized 1-Palmitoyl-2-Arachidonoyl-Sn-Glycero-3 Phosphocholine Products in Uremic Patients by LC-ESI/MS
    Chang, Chiz-Tzung
    Chang, I-Ting
    Hsia, Min-Hui
    Wang, Chun-Cheng
    Chen, Chao-Jung
    Zou, Hsin-Bai
    Chen, Yu-Qing
    Chiu, Wen-Chien
    Lin, Zhi-Ru
    Liu, Mine-Yine
    SEPARATIONS, 2022, 9 (08)
  • [38] METABOLISM OF 1-ACYL-2-ACETYL-SN-GLYCERO-3-PHOSPHOCHOLINE (ACAPC)
    TRIGGIANI, M
    CHILTON, FH
    FASEB JOURNAL, 1991, 5 (04): : A897 - A897
  • [39] Hemolytic Activity of Membrane-Active Peptides Correlates with the Thermodynamics of Binding to 1-Palmitoyl-2-Oleoyl-sn-Glycero-3-Phosphocholine Bilayers
    Spaller, B. Logan
    Trieu, Julie M.
    Almeida, Paulo F.
    JOURNAL OF MEMBRANE BIOLOGY, 2013, 246 (03): : 257 - 262
  • [40] AUGMENTATION OF IMMUNOGLOBULIN-SYNTHESIS BY THE PLATELET-ACTIVATING-FACTOR ANALOG 1-PALMITOYL-2-ACETOYL-SN-GLYCERO-3-PHOSPHOCHOLINE IN HUMAN B-LYMPHOCYTES
    MAZER, B
    BASTIEN, Y
    SARIRIAN, M
    JOURNAL OF ALLERGY AND CLINICAL IMMUNOLOGY, 1994, 93 (01) : 203 - 203
12345