- Synthesis and biological activity of phosphoglycolipids from Thermus thermophilus
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An extreme thermophile, Thermus thermophilus, has very unique glycolipids on the cell surface. The acidic immunostimulatory phosphoglycolipid of T. thermophilus was synthesized for the first time, with newly developed glycosylation methods using 3-nitropyridyl (3NPy) and 4,6-dimethoxy-1,3,5- triazin-2-yl (DMT) glycosides as glycosyl donors. The analogues of the phosphoglycolipid, which include a diastereomer possessing the opposite configuration at the diacyl glycerol moiety, were also synthesized. The biological activities of the synthesized compounds were elucidated with cytokine inductions (IL-6 and TNF-α). A synthetic phosphoglycolipid with a natural-type diacyl glycerol configuration showed apparent immunostimulatory activity, whereas its diastereomer did not. The present study revealed that the configuration at the diacyl glycerol moiety of the phosphoglycolipids is important for immunostimulation, suggesting the existence of the particular receptor/recognizing protein that can recognize the stereochemistry of the glycerol part.
- Fujimoto, Yukari,Mitsunobe, Kunihiro,Fujiwara, Satoko,Mori, Motoko,Hashimoto, Masahiro,Suda, Yasuo,Kusumoto, Shoichi,Fukase, Koichi
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supporting information
p. 5034 - 5041
(2013/08/23)
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- Readily available and recoverable chiral ionic phosphite ligands for the highly enantioselective hydrogenation of functionalized olefins
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A series of novel ionic phosphite ligands bearing carbohydrate groups were conveniently synthesized and successfully applied in the asymmetric hydrogenation of enamides, α-dehydroamino acid esters, and dimethyl itaconate. High efficiency and excellent reu
- Zhao, Yingwei,Huang, Hanmin,Shao, Jianping,Xia, Chungu
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scheme or table
p. 769 - 774
(2011/08/06)
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- New 3-O-lauroyl-2-O-benzyl-glycerol sulfonate
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The hydroxy groups of D-mannitol were protected by the formation of acetals and benzylethers and then 2-O-benzyl-D-glyceraldehyde dimethylacetal was prepared after the deprotection and oxygenolysis of the protected D-mannitol. In the presence of DCC and D
- Han, Liang,Li, Zheng-Ming,Gao, Jian-Rong
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p. 503 - 505
(2008/09/21)
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- Synthesis of amphiphilic polyhydroxylated pyrrolidines as potential glycosidase inhibitors
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Several polyhydroxylated pyrrolidines with an aliphatic long chain on the ring nitrogen were prepared starting from D-mannitol. An amphiphilic bis- azasugar scaffold has been also prepared. These products behave as cationic surfactants and show a promising anti HIV-1 activity.
- Esposito, Annamaria,Falorni, Massimo,Taddei, Maurizio
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p. 6543 - 6546
(2007/10/03)
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- New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis
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A convenient synthesis of new and enantiometrically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described.Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol.These intermediates are converted to 2-O-benzyl- or 2-O-alkyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol.The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition.Also, triglycerides with three different alkyl chains, ester of ether, can be prepared.As an example of the varsatility of the new intermediates, we describe the synthesis of 1-O-hexadecyl-2-O-acetyl-sn-glycero-3-phosphocho;ine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol. Keywords: Synthetic phospholipids; PAF; Phospholipid analogues; Synthesis; Chiral pool; Glyceraldehyde; C-3 building blocks; Optical purity
- Massing, Ulrich,Eibl, Hansjoerg
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p. 211 - 224
(2007/10/02)
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