88988-71-0Relevant academic research and scientific papers
Synthesis of lipids for development of multifunctional lipid-based drug-carriers
Zhu, Guodong,Alhamhoom, Yahya,Cummings, Brian S.,Arnold, Robert D.
experimental part, p. 6370 - 6375 (2011/12/02)
A simple approach to synthesize phospholipids to modulate drug release and track lipid-based particulate drug-carriers is described. We synthesized two ether lipids, 1 1-O-hexadecyl-2-pentadenoyl-sn-glycerol-3-phosphocholine (C 31PC) and 2 1-O-
Enzymatic Release of Antitumor Ether Lipids by Specific Phospholipase A2 Activation of Liposome-Forming Prodrugs
Andresen, Thomas L.,Davidsen, Jesper,Begtrup, Mikael,Mouritsen, Ole G.,J?rgensen, Kent
, p. 1694 - 1703 (2007/10/03)
An enzymatically activated liposome-based drug-delivery concept involving masked antitumor ether lipids (AELs) has been investigated. This concept takes advantage of the cytotoxic properties of AEL drugs as well as the membrane permeability enhancing prop
Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line
Lindberg, Jan,Svensson, Stefan C.T,P?hlsson, Peter,Konradsson, Peter
, p. 5109 - 5117 (2007/10/03)
Synthesis of three galactoglycerolipids (3-O-(β-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(α-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl)-1-O- hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(α-D-galactopyranosyl-(1→4)-β-D-galactopyranosyl)-1-O- hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development.
Stereoselective Synthesis of 1-O-Alkyl-3-O-benzyl-sn-glycerols and 1-O-Alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerols
Bauer, Friederike,Ruess, Klaus-Peter,Lieflaender, Manfred
, p. 765 - 768 (2007/10/02)
Starting with D-mannitol, the yield of th synthesis of 3-O-benzyl-sn-glycerol (1) could be improved.The regioselective alkylation of 1 at the primary hydroxy group to the 1-O-alkyl-3-O-benzyl-sn-glycerols 3 was achieved by using the dibutylstannylene protecting group.The 1-O-alkyl-2-O-methyl-sn-glycerols 4, readily obtainable from 3, were successfully glycosylated under the conditions of the Koenigs-Knorr reaction to give 1-O-alkyl-2-O-methyl-3-O-β-D-glycosyl-sn-glycerols. - Key Words: Lysoglycolipids, glyceryl ethers / Stereoselective synthesis / Koenigs-Knorr reaction / Glyceryl ethers
The Chemistry of L-Ascorbic and D-Isoascorbic Acids. 2. R and S Glyceraldehydes from a Common Intermediate
Mikkilineni, Amarendra B.,Kumar, Praveen,Abushanab, Elie
, p. 6005 - 6009 (2007/10/02)
(R)- and (S)-glyceraldehyde and glycerol derivatives have been prepared from (2R,3S)-1,2-O-isopropylidenebutane-1,2,3,4-tetrol. (2R,3S)- and (2S,3S)-1,2-O-benzylidenebutane-1,2,3,4-tetrol have been prepared and cleaved to give (R)- and (S)-1,2-O-benzylideneglyceraldehydes and -glycerols.The conservation of chirality and conversion to PAF analogues are also demonstrated.
