62502-71-0Relevant academic research and scientific papers
Osmotic stability of muramyl dipeptide-bearing liposomes and molecular miscibility in their membranes
Kim, Suhk-Mann,Kiyonaga, Hiroshi,Yamaguchi, Hideto,Morozumi, Hiroto,Fujiwara, Toshimichi,Ando, Shuichi,Tsuge, Hideya,Akutsu, Hideo
, p. 541 - 548 (1999)
Muramyl dipeptide is the minimal and essential structural unit for the immunopotentiating activities of bacterial cell walls. The muramyl dipeptide derivative N-acetyl-6-O-(2-tetradecylhexadecanol)muramyl-L-alanyl-D- isoglutamine (B30-MDP) and its amide derivative (B30-MDPA) are good basic materials for use in artificial liposome vaccines (virosomes). The osmotic stability of muramyl dipeptide-bearing liposomes composed of various binary mixtures was examined to find conditions favoring stable liposome formation. The osmotic properties of B30-MDP-bearing and B30-MDPA-bearing liposomes were significantly different from each other. Nevertheless, a good correlation between osmotic stability and virosome formation was found for both types of liposomes. Furthermore, the dynamic structures and the intermolecular interactions of phospholipids in muramyl dipeptide-bearing liposomes were investigated by solid-state 2H and 31PNMR. The results suggested that molecular miscibility in the liposomes is not an essential factor for osmotic stability. Negative charges on the liposome surface and flexible hydrophilic moieties were found to be the most important factors in keeping isolated liposomes osmotically stable.
A convenient and effective method for the regioselective deuteration of alcohols
Maegawa, Tomohiro,Fujiwara, Yuta,Inagaki, Yuya,Monguchi, Yasunari,Sajiki, Hironao
supporting information; experimental part, p. 2215 - 2218 (2009/10/02)
The convenient and regioselective deuteration of hydroxy groups on vicinal carbons was achieved by the combination of 5% ruthenium on carbon (Ru/C), hydrogen gas and deuterium oxide (D2O).
Microdomain formation in phosphatidylethanolamine bilayers detected by 2H-NMR
Shin, Kyong-Hwa,Nagamori, Toshiaki,Kimura, Yasuhiro,Tomoi, Masao,Fujiwara, Toshimichi,Akutsu, Hideo
, p. 55 - 62 (2007/10/02)
In deuterium NMR spectra of phosphatidylethanolamine bilayers with an extremely high content of saturated fatty acids, each C1 deuteron of the glycerol backbone gave rise to a doublet. This suggests the presence of two backbone conformations, the exchange between which is slow on an NMR time-scale. The origin of the two conformations has been investigated in this work using saturated 1,2-diacyl-sn-glycero-3-phosphoethanolamine specifically deuterated in the glycerol backbone. The results showed that the two conformations originate from different domains, which have different fatty acid compositions. The differential scanning calorimetry of the bilayers suggested that the size of the domain is not large enough to show an independent phase transition. Thus, the formation of microdomains in the phosphatidylethanolamine bilayers has been concluded. Conformational difference in different domains was shown to be restricted to the C1 position of the glycerol backbone. The microdomains of phosphatidylethanolamine were retained even in the presence of other phospholipids.
Total synthesis of perdeuterated phospholipids
Bersch, B.,Starck, J. P.,Milon, A.,Nakatani, Y.,Ourisson, G.
, p. 575 - 583 (2007/10/02)
A general method for the total synthesis of various perdeuterated phospholipids (DMPA, DMPG, DMPE, DMPC) is described.Starting from simple and easily obtainable deuterated precursors, perdeuterated phosphatidic acid (DMPA-d59) was synthesized.DMPA-d59 was coupled to various perdeuterated alcohols in the presence of alkylsulfonyl chlorides as condensing agents.The preparation of the perdeuterated alcohols is also presented.The major advantage of this method lies in the independent synthesis of DMPA and the alcohol moieties, allowing the transformation to the desired phospholipid class in the final reaction step.The reaction scheme presented here can also be used for the synthesis of selectively deuterated phospholipids.Keywords - perdeuterated phospholipids / phosphatidic acid-d59 / phosphatidylglycerol-d64 / phosphatidylcholine-d72 / phopshatidylethanolamine-d63 / total synthesis
