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Lipopolysaccharide

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
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Lipid A from Escherichia coli 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2001LipopolysaccharideShoichi Kusumoto#506, LA-15-PH C94H178N2O25P2 1798.365Download ChemDraw structure dataIL-6 induction, TNF-a induction, Limulus activity ED50; << Ref. 2001>> 1H NMR (600 MHz, CD3OD / CDCl3 = 1 : 1) d = 5.47 (dd, J= 5.8, 2.9 Hz, 1H), 5.24-5.16 (m, 3H), 5.09 (t, J= 8.1 Hz, 1H), 4.55 (d, J= 7.0 Hz, 1H), 4.25 (dd, J= 16.0, 7.9 Hz, 1H), 4.18 (m, 1H), 4.13 (m, 1H), 4.07 (d, J= 9.8 Hz, 1H), 4.02 (dd, J= 11.2, 1.8 Hz, 1H), 4.00 (m, 1H), 3.94-3.87 (m, 2H), 3.84 (dd, J= 10.0, 5.0 Hz, 1H), 3.76 (d, J= 11.4 Hz, 1H), 3.49 (t, J= 7.7 Hz, 1H), 3.37 (m, 1H), 2.71 (dd, J= 13.5, 6.2 Hz, 1H), 2.64 (dd, J= 13.5, 4.3 Hz, 1H), 2.51 (dd, J= 12.6, 7.0 Hz, 1H), 2.50 (dd, J= 12.6, 3.7 Hz, 1H), 2.43 (dd, J= 12.6, 4.0 Hz, 1H), 2.41 (dd,J= 13.1, 7.7 Hz, 1H), 2.35-2.29 (m, 4H), 2.26-2.22 (m, 1H), 2.25 (dd, J= 12.0, 8.0 Hz, 1H), 1.67-1.40 (m, 12H), 1.38-1.22 (m, 108H), 0.89 (t, J= 5.9 Hz, 18H).; << Ref. 2001>> FAB-MS (negative) m/z 1797 [(M-H)-] liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 8 : 8 : 6 : 1 Escherichia coli Coupling of the trichloroacetimidate donor with the glycosyl acceptor, which were prepared from allyl 4,6-O-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-D-glucopyranoside, was carried out by the use of tin(II) trifluororomethanesulfonate as a catalyst to give the desired b(1a_right6) disaccharide. Acylation of the 3-position with (R)-3-(benzyloxy)-tetradecanoic acid proceeded smoothly. Deprotection of N2,2,2-trichloroethoxycarbonyl group at the 2'-position was followed by N-acylation with (R)-3-(dodecanoyloxy)-tetradecanoic acid by using DCC. For the introduction of the phosphoryl group at the 1-position, the 1-O-allyl group was then removed. The hydroxy group was then phosphorylated with tetrabenzyl diphosphate to give the 1-a-phosphate. Finally, hydrogenolysis (7 kgcm-2 of hydrogen and Pd-black) of all the benzyl-type protecting groups furnished the desired E-coli lipid A.; << Ref. 2001>> << Ref.2001 >> AUTHOR: Wen-Ci Liu, Oikawa,M., Fukase,K., Suda,Y., and Kusumoto,S. TITLE: A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues. JOURNAL: Bull. Chem. Soc. Jpn VOLUME: 72 PAGE: 1377 -1385 (1999)
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Biosynthetic precursor of lipid A from Escherichia coli 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2002LipopolysaccharideShoichi Kusumoto#406, LA-14-PP C68H130N2O23P2 1405.707Download ChemDraw structure dataIL-6 inhibiting activity; << Ref. 2007>> 1H NMR (500 MHz, DMSO-d6) d=8.76(br s, 1H), 7.32 (d, J=9.0Hz, 1H), 5.24 (dd, J=6.6,1.8Hz, 1H), 5.03 (dd, J=9.9,9.9Hz, 1H), 4.89 (dd, J=11.7,6.4Hz, 1H), 4.88 (d, J=8.2Hz, 1H), 4.03 (ddd, J=6.4,6.4,6.4Hz, 1H), 3.98 (m, 1H), 3.95 (ddd, J=9.0,9.0,1,8Hz, 1H), 3.87 (ddd, J=136.0,12.5,2.7Hz, 1H), 3.85,3.83,3.73 and 3.72 (m, 1H each), 3.77(dd, J=11.7,8.2Hz, 1H), 3.75 (m, 1H), 3.70 (ddd, J=140.0,12.5,6.3Hz, 1H), 3.53 (m, 1H), 3.33 (m, 1H), 3.13 (m, 1H), 2.47 (dd, J= 6.7,13.1Hz, 1H), 2.41 (dd, J= 6.7,15.8Hz, 1H), 2.34 (dd, J= 6.7,15.8Hz, 1H), 2.31-2.26, 2.31-2.26, 2.18-2.13, and 2.18-2.13(m, 1H each), 2.08 (dd, J= 5.5,13.1Hz, 1H), 1.44-1.21 (m,80H), 0.92 (t, J=6.9Hz, 12H).; << Ref. 2005>> ESI-MS (negative, API III) m/z 1404.9 [(M-H)-] liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001 Escherichia coli Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine.; << Ref. 2004/2005/2006>> << Ref.2004 >> AUTHOR: Oikawa,M., Wada,A., Yishizaki,H., Fukase,K., and Kusumoto, S. TITLE: New Efficient Synthesis of a Biosynthetic Precursor of Lipid A. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 70 PAGE: 1435 -1440 (1997)
<< Ref.2005 >> AUTHOR: Imoto,M., Yoshimura,H., Yamamoto,M. Shimamoto,T., Kusumoto, S., and Shiba, T. TITLE: Chemical Synthesis of Phosphorylated Tetraacyl Disaccaride Corresponding to a Biosynthetic precursor of Lipid A. JOURNAL: Tetrahedron Lett. VOLUME: 25 PAGE: 2667 -2670 (1984)
<< Ref.2006 >> AUTHOR: Imoto,M., Yoshimura,H., Yamamoto,M., Shimamoto,T., Kusumoto, S., and Shiba, T. TITLE: Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure. JOURNAL: Bull. Chem. Soc. Jpn VOLUME: 60 PAGE: 2197 -2204 (1987)
<< Ref.2007 >> AUTHOR: Fukase,K., Fukase,Y., Oikawa,M., Wen-Chi Liu, Suda.Y., and Kusumoto, S. TITLE: Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains. JOURNAL: Tetrahedron VOLUME: 54 PAGE: 4033 -4050 (1998)
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Lipid A analogue of shorter acyl chains 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2003LipopolysaccharideShoichi Kusumoto C52H98N2O23P2 1181.282Download ChemDraw structure data a]d-24 -21.0 (c 0.03, H2O) 1H NMR (500 MHz, D2O) d=5.36(br s, 1H, H1), 5.16 (m, 1H, H3.), 5.15 (m, 1H, H3), 4.63 (m, 1H, H1.), 4.11 (m, 1H, H2), 4.09 (m, 1H, H4.), 4.08 (m, 1H, H6a), 3.99 (m, 1H, H2.), 3.98,3.97,3.92 and 3.92 (m, 1H each, one of oxymethine protons on acyl groups), 3.95 (m, 1H, H5), 3.84 (m, 1H, H6a.), 3.83 (m, 1H, H6b), 3.80 (m, 1H, H4), 3.75 (m, 1H, H6b.), 3.60 (m, 1H, H5.), 2.59 (dd, J=15.9,5.4Hz, 1H, one of a-CH2 protons on acyl groups), 2.50,2.45,2.39,2.38,2.30,2.25 and 2.25 (m, 1H each, one of a-CH2 protons on acyl groups), 1.50-1.16 (m, 48H, CH2 on acyl groups), 0.86-0.76 (m, 12H, CH3 on acyl groups).; << Ref. 2007>> ESI-MS (nagative) m/z 1179.7 [(M-H)-], 589.1 [(M-2H)2-] liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001 << Ref. 2007>>Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)decanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine. << Ref.2007 >> AUTHOR: Fukase,K., Fukase,Y., Oikawa,M., Wen-Chi Liu, Suda.Y., and Kusumoto, S. TITLE: Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains. JOURNAL: Tetrahedron VOLUME: 54 PAGE: 4033 -4050 (1998)
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Biosynthetic precursor of lipid A analogue of shorter acyl chains 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2004LipopolysaccharideShoichi Kusumoto C60H114N2O23P2 1293.494Download ChemDraw structure dataIL-6 inhibiting activity; << Ref. 2007>> ESI-MS (nagative) m/z 1291.6 [(M-H)-], 645.3 [(M-2H)2-] liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001 << Ref. 2007>>Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)decanoic acid and (R)-3-(benzyloxy)tetradecanoic acid then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection, followed by purification by liquid-liquid partition chromatography, afforded the target compound in 2.9% total yields through 13 steps from N-Troc D-glucosamine. << Ref.2007 >> AUTHOR: Fukase,K., Fukase,Y., Oikawa,M., Wen-Chi Liu, Suda.Y., and Kusumoto, S. TITLE: Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains. JOURNAL: Tetrahedron VOLUME: 54 PAGE: 4033 -4050 (1998)
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6-13C-labeled biosynthetic precursor of lipid A 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-(6-13C)-glucopyranose 1,4'-Bisphosphate CLS2005LipopolysaccharideShoichi Kusumoto#406, LA-15-PH C68H130N2O23P2 1405.707Download ChemDraw structure dataIL-6 inhibiting activity; << Ref. 2001>> 1H NMR (500 MHz, DMSO-d6) d=8.76 (br s, 1H), 7.32 (d, J=9.0Hz, 1H), 5.24 (dd, J=6.6,1.8Hz,1H), 5.03 (dd, J=9.9,9.9Hz, 1H), 4.89 (dd, J=11.7,6.4Hz, 1H), 4.88 (d, J=8.2Hz,1H), 4.03 (ddd, J=6.4,6.4,6.4Hz, 1H), 3.98 (m, 1H), 3.95 (ddd, J=9.0,9.0,1,8Hz, 1H), 3.87 (ddd, J=136.0,12.5,2.7Hz, 1H), 3.85,3.83,3.73 and 3.72 (m, 1H), 3.77 (dd, J=11.7,8.2Hz, 1H), 3.75 (m, 1H), 3.70 (ddd, J=140.0,12.5,6.3Hz, 1H), 3.53 (m, 1H), 3.33 (m, 1H), 3.13 (m, 1H), 2.47 (dd, J= 6.7,13.1Hz, 1H), 2.41 (dd, J= 6.7,15.8Hz, 1H), 2.34 (dd, J= 6.7,15.8Hz, 1H), 2.31-2.26, 2.31-2.26, 2.18-2.13, and 2.18-2.13 (m, 1H each), 2.08 (dd, J= 5.5,13.1Hz, 1H), 1.44-1.21 (m, 80H), 0.92 (t, J=6.9Hz,12H); 13C NMR (125.65 MHz, DMSO-d6) d = 66.4 (C6).; << Ref. 2009>> ESI-MS (nagative API III) m/z 1404.9 [(M-H)-] liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001 Escherichia coli << Ref. 2009>>D-(6-13C)Glucose was converted into a suitably protected glucosamine derivative via 1,6-anhydro-b-D-glucose. After coupling with glycosyl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 1.7%, respectively, for a total of 18 steps from D-(6-13C)glucose. << Ref.2001 >> AUTHOR: Wen-Ci Liu, Oikawa,M., Fukase,K., Suda,Y., and Kusumoto,S. TITLE: A Divergent Synthesis of Lipid A and Its Chemically Stable Unnatural Analogues. JOURNAL: Bull. Chem. Soc. Jpn VOLUME: 72 PAGE: 1377 -1385 (1999)
<< Ref.2009 >> AUTHOR: Oikawa,M., Shintaku,T., Sekljik,H., Fukase,K., and Kusumoto, S. TITLE: Synthesis of 13C-Labeled Biosynthetic Precursor of Lipid A and Its Analogue with Shorter Acyl Chains. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 72 PAGE: 1857 -1867 (1999)
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6-13C-labeled lipid A analogue of shorter acyl chains 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxydecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxydecanoyl]-2-O-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2006LipopolysaccharideShoichi Kusumoto C52H98N2O23P2 1181.282Download ChemDraw structure data [a]d-24 -21.0 (c 0.03, H2O) 1H NMR (500 MHz, D2O) d=5.36 (br s, 1H, H1), 5.16 (m, 1H, H3.), 5.15 (m, 1H, H3), 4.63(m, 1H, H1.), 4.11 (m, 1H, H2), 4.09 (m, 1H, H4.), 4.08 (m, 1H, H6a), 3.99 (m, 1H, H2.), 3.98,3.97,3.92 and 3.92 (m, 1H each, one of oxymethine protons on acyl groups), 3.95 (m, 1H, H5), 3.84 (m, 1H, H6a.), 3.83 (m, 1H, H6b), 3.80 (m, 1H, H4), 3.75 (m, 1H, H6b.), 3.60 (m, 1H, H5.), 2.59 (dd, J=15.9,5.4Hz, 1H, one of a-CH2 protons on acyl groups), 2.50,2.45,2.39,2.38,2.30,2.25 and 2.25 (m, 1H each, one of a-CH2 protons on acyl groups), 1.50-1.16 (m, 48H, CH2 on acyl groups), 0.86-0.76 (m, 12H, CH3 on acyl groups); 13C NMR (125.65 MHz, D2O) d = 68.5 (C6).; << Ref. 2007>> ESI-MS (nagative) m/z 1179.7 [(M-H)-], 589.1 [(M-2H)2-] liquid-liquid partition column chromatography; Sephadex LH-20, chroloform / methanol / isopropyl alchol / water / triethylamine = 20 : 20 : 2.5 : 22.5 : 0.001 D-(6-13C)Glucose was converted into a suitably protected glucosamine derivative via 1,6-anhydro-b-D-glucose. After coupling with glycosyl donors, the desired compounds were synthesized through a 6-step reaction sequence. The total yields were 6.4%, respectively, for a total of 18 steps from D-(6-13C)glucose.; << Ref. 2009>> << Ref.2007 >> AUTHOR: Fukase,K., Fukase,Y., Oikawa,M., Wen-Chi Liu, Suda.Y., and Kusumoto, S. TITLE: Divergent Synthesis and Biological Activities of Lipid A Analogues of Shorter Acyl Chains. JOURNAL: Tetrahedron VOLUME: 54 PAGE: 4033 -4050 (1998)
<< Ref.2009 >> AUTHOR: Oikawa,M., Shintaku,T., Sekljik,H., Fukase,K., and Kusumoto, S. TITLE: Synthesis of 13C-Labeled Biosynthetic Precursor of Lipid A and Its Analogue with Shorter Acyl Chains. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 72 PAGE: 1857 -1867 (1999)
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Lipid A from Escherichia coli hydroxy analogue of fatty acid S-type 2-Deoxy-6-O-[2-deoxy-2-[(S)-3-(dodecanoyloxy)tetradecanoylamino]-3-O-[(S)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(S)-3-hydroxytetradecanoyl]-2-[(S)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2007LipopolysaccharideShoichi Kusumoto C94H178N2O25P2 1798.365Download ChemDraw structure dataIL-6 induction; << Ref. 2010>> 1H NMR (500 MHz, CDCl3 ) d = 5.55 (dd, J= 5.8, 2.9 Hz, 1H), 5.22-5.18 (m, 4H), 4.77 (d, J= 8.7 Hz, 1H), 4.27-4.21 (m, 2H), 4.09- 4.03 (m, 2H), 3.90-3.75 (m, 6H), 3.55 (dd, J= 9.6, 9.6 Hz, 1H), 3.49 -3.47 (m, 1H), 2.70 (dd, J= 16.7, 4.8 Hz, 1H), 2.62-2.55 (m, 2H), 2.49-2.47 (m, 2H), 2.43-2.35 (m, 2H), 2.34-2.27 (m, 4H), 2.26-2.22 (m, 1H), 1.66-1.54 (m, 8H), 1.53-1.42 (m, 4H), 1.40-1.24 (m, 108H), 0.88 (t, J= 6.9 Hz, 18H).; << Ref. 2010>> FAB-MS (negative) m/z 1797 [(M-H)-] centrifugal partition chromatography; n-buthanol / THF / water / triethylamine = 45 : 35 : 100 : 0.02, 1600rpm.<< Ref. 2010>> Coupling of the trichloroacetimidate donor with the glycosyl acceptor, which were prepared from allyl 4,6-O-benzylidene-2-deoxy-2-(trichloroethoxycarbonylamino)-D-glucopyranoside, was carried out by the use of tin(II) trifluororomethanesulfonate as a catalyst to give the desired b(1a_right6) disaccharide. Acylation of the 3-position with (S)-3-(benzyloxy)-tetradecanoic acid proceeded smoothly. Deprotection of N2,2,2-trichloroethoxycarbonyl group at the 2'-position was followed by N-acylation with (S)-3-(dodecanoyloxy)-tetradecanoic acid. For the introduction of the phosphoryl group at the 1-position, the 1-O-allyl group was then removed. The hydroxy group was then phosphorylated with tetrabenzyl diphosphate to give the 1-a-phosphate. Finally, hydrogenolysis (7 kgcm-2 of hydrogen and Pd-black) of all the benzyl-type protecting groups furnished the desired E-coli lipidA.; << Ref. 2010>> << Ref.2010 >> AUTHOR: Liu,Wen-Chi, Oikawa,M., Suda,Y, Fukase,K., Winarno,H., Mori,S., Hashimoto,M., and Kusumoto, S. TITLE: Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 70 PAGE: 1441 -1450 (1997)
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Biosynthetic precursor of lipid A analogue with hydroxy fatty acid S-type 2-Deoxy-6-O-[2-deoxy-3-O-[(S)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(S)-3-hydroxytetradecanoylamino]-a-D-glucopyranose 1,4'-Bisphosphate CLS2008LipopolysaccharideShoichi Kusumoto C68H130N2O23P2 1405.707Download ChemDraw structure dataIL-6 inhibiting activity; << Ref. 2010>> FAB-MS (nagative) m/z 1403 [(M-H)-] centrifugal partition chromatography; n-buthanol / THF / water / triethylamine = 45 : 35 : 100 : 0.02, 1600rpm.; << Ref. 2010>> Two appropriately modified acyl-substituted glucosamine units were synthesized from D-glucosamine using (R)-3-(benzyloxy)tetradecanoic acid and then coupled by the Lewis acid-promoted glycosidation via the corresponding trichloroacetoimidate. Glycosyl phosphorylation and hydrogenolytic deprotection afforded the target compound through 13 steps from N-Troc D-glucosamine.; << Ref. 2004/2005/2006>> << Ref.2004 >> AUTHOR: Oikawa,M., Wada,A., Yishizaki,H., Fukase,K., and Kusumoto, S. TITLE: New Efficient Synthesis of a Biosynthetic Precursor of Lipid A. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 70 PAGE: 1435 -1440 (1997)
<< Ref.2005 >> AUTHOR: Imoto,M., Yoshimura,H., Yamamoto,M. Shimamoto,T., Kusumoto, S., and Shiba, T. TITLE: Chemical Synthesis of Phosphorylated Tetraacyl Disaccaride Corresponding to a Biosynthetic precursor of Lipid A. JOURNAL: Tetrahedron Lett. VOLUME: 25 PAGE: 2667 -2670 (1984)
<< Ref.2006 >> AUTHOR: Imoto,M., Yoshimura,H., Yamamoto,M., Shimamoto,T., Kusumoto, S., and Shiba, T. TITLE: Chemical Synthesis of a Biosynthetic Precursor of Lipid A with a Phosphorylated Tetraacyl Disaccharide Structure. JOURNAL: Bull. Chem. Soc. Jpn VOLUME: 60 PAGE: 2197 -2204 (1987)
<< Ref.2010 >> AUTHOR: Liu,Wen-Chi, Oikawa,M., Suda,Y, Fukase,K., Winarno,H., Mori,S., Hashimoto,M., and Kusumoto, S. TITLE: Enzymatic Preparation of (S)-3-Hydroxytetradecanoic Acid and Synthesis of Unnatural Analogues of Lipid A Containing the (S)-Acid. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 70 PAGE: 1441 -1450 (1997)
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a-phosphonooxyethyl analogue of lipid A from Escherichia coli 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-1-O-(phosphonooxy)ethyl -a-D-glucopyranoside CLS2009LipopolysaccharideShoichi Kusumoto#PE-1 C96H182N2O26P2 1842.418Download ChemDraw structure dataIL-6 induction, TNF-a induction, Limulus activity ED50 2 pg/mL; << Ref. 2011>> 1H NMR(600 MHz, CD3OD/CDCl3 =1:1) d = 5.23 (m, 1H), 5.19 (t, J= 8.2 Hz, 1H), 5.17 (m, 1H), 5.14 (t, J= 8.2 Hz, 1H), 4.82(d, J= 3.0 Hz, 1H), 4.56(d, J= 7.4 Hz, 1H), 4.23(q, J= 8.0 Hz, 1H), 4.18 (dd, J= 8.9,3.0 Hz, 1H), 4.08-3.93 (m, 5H), 3.92- 3.82 (m, 4H), 3.80 (dd, J= 10.3,4.5 Hz, 1H), 3.74 (d, J= 10.6 Hz, 1H), 3.63 (m, 1H), 3.56 (t, J= 8.1 Hz, 1H), 3.37 (m, 1H), 2.72 (dd, J= 14.0, 6.6 Hz, 1H), 2.64 (dd, J= 14.0,4.5 Hz, 1H), 2.52-2.36 (m, 2H), 2.36-2.27 (m, 6H), 1.66-1.39 (m, 12H), 1.38-1.20 (m, 108H), 0.89 (t, J= 5.6 Hz, 18H).; << Ref. 2011>> FAB-MS (negative) m/z 1840 [(M-H)-] liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 15 : 15: 15 : 2 << Ref. 2011>> << Ref.2011 >> AUTHOR: Liu,Wen-Chi, Oikawa,M., Suda,Y, Fukase,K., and Kusumoto, S. TITLE: A Divergent Synthesis of Lipid A and Its Chemically Stable Unnnatural Analogues. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 72 PAGE: 1337 -1385 (1999)
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a-carboxymethyl analogue of lipid A from Escherichia coli 1-O-Carboxymethyl-2-deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphoryl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranose CLS2010LipopolysaccharideShoichi Kusumoto#CM-506 C96H179N2O24P 1776.421Download ChemDraw structure dataIL-6 induction, TNF-a induction, Limulus activity ED50 1 pg/mL; << Ref. 2011>> 1H NMR(600 MHz, CD3OD/CDCl3 =1:1) d = 5.26-5.17 (m, 2H), 5.23 (t, J= 8.4 Hz, 1H), 5.16 (t, J= 9.1 Hz, 1H), 4.78 (d, J= 3.1 Hz, 1H), 4.65 (d, J= 6.9 Hz, 1H), 4.20-4.14 (m, 2H), 4.09(d, J= 12.5 Hz, 1H), 4.08-3.98 (m, 2H), 3.94 (m, 1H), 3.86 (d, J= 12.5 HZ, 1H), 3.91-3.65 (m, 5H), 3.52(t, J= 8.0 Hz, 1H), 3.36 (m, 1H), 2.82 (dd, J= 13.7, 5.4 Hz, 1H), 2.64 (dd, J= 13.7, 4.7 Hz, 1H), 2.54-2.36 (m, 4H), 2.36-2.24 (m, 6H), 1.68-1.40 (m, 12H), 1.39-1.21 (m, 108H), 0.89 (t, J= 5.8 Hz, 18H).; << Ref. 2011>> FAB-MS (negative) m/z 1774[(M-H)-] liquid-liquid partition column chromatography; 20 g of Sephadex LH-20, chroloform / methanol / water / isopropyl alchol = 100 : 100: 100 : 13 << Ref. 2011>> << Ref.2011 >> AUTHOR: Liu,Wen-Chi, Oikawa,M., Suda,Y, Fukase,K., and Kusumoto, S. TITLE: A Divergent Synthesis of Lipid A and Its Chemically Stable Unnnatural Analogues. JOURNAL: Bull. Chem. Soc. Jpn. VOLUME: 72 PAGE: 1337 -1385 (1999)
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a-phosphonooxyethyl analogue of lipid A from Escherichia coli with nonhydroxylated lipid 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphoryl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-1-O-(phosphonooxy)ethyl-3-O-[(R)-tetradecanoyl]-2-[(R)-tetradecanoylamino]-a-D-glucopyranoside CLS2011LipopolysaccharideShoichi Kusumoto#PE-2 C96H182N2O24P2 1810.419Download ChemDraw structure dataIL-6 induction, TNF-a induction; << Ref. 2012>> << Ref. 2013>> << Ref.2012 >> AUTHOR: Kirikae, T., Schade, F. U., Zahringer, U., Kirikae, F., Brade, H., Kusumoto, S., Kusama, T., and Rietschel, E. T. TITLE: The significance of the hydrophilic backbone and the hydrophobic fatty acid regions of lipid A for macrophage binding and cytokine induction PubMed ID:8156049 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 8 PAGE: 13-26(1994)
<< Ref.2013 >> AUTHOR: Kusama, T., Soga, T., Shioya, E., Nakayama, K., Nakajima, H., Osada, Y., Ono, Y., Kusumoto, S., and Shiba, T. TITLE: Synthesis and antitumor activity of lipid A analogs having a phosphonooxyethyl group with alpha- or beta-configuration at position 1 PubMed ID:2092933 JOURNAL: Chem Pharm Bull (Tokyo). VOLUME: 38 PAGE: 3366-3372(1990)
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b-phosphonooxyethyl analogue of lipid A from Escherichia coli 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(dodecanoyloxy)tetradecanoylamino]-4-O-phosphonyl-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-b-D-glucopyranosyl]-1-O-(phosphonooxy)ethyl-3-O-[(R)-tetradecanoyl]-2-[(R)-tetradecanoylamino]-b-D-glucopyranoside CLS2012LipopolysaccharideShoichi Kusumoto#PE-3 C96H182N2O24P2 1810.419Download ChemDraw structure dataIL-6 induction, TNF-a induction; << Ref. 2012>> << Ref. 2013>> << Ref.2012 >> AUTHOR: Kirikae, T., Schade, F. U., Zahringer, U., Kirikae, F., Brade, H., Kusumoto, S., Kusama, T., and Rietschel, E. T. TITLE: The significance of the hydrophilic backbone and the hydrophobic fatty acid regions of lipid A for macrophage binding and cytokine induction PubMed ID:8156049 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 8 PAGE: 13-26(1994)
<< Ref.2013 >> AUTHOR: Kusama, T., Soga, T., Shioya, E., Nakayama, K., Nakajima, H., Osada, Y., Ono, Y., Kusumoto, S., and Shiba, T. TITLE: Synthesis and antitumor activity of lipid A analogs having a phosphonooxyethyl group with alpha- or beta-configuration at position 1 PubMed ID:2092933 JOURNAL: Chem Pharm Bull (Tokyo). VOLUME: 38 PAGE: 3366-3372(1990)
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a-phosphonooxyethyl analogue of biosynthetic precursor of lipid A from Eschericha coli 2-(Phosphonooxy)ethyl-2-deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranoside CLS2013LipopolysaccharideShoichi Kusumoto#PE-4 C70H134N2O24P2 1449.760Download ChemDraw structure dataIL-6 induction, TNF-a induction; << Ref. 2012>> ESI-MS (nagative, API III) m/z 1404.9 [(M-H)-] << Ref. 2013>> << Ref.2012 >> AUTHOR: Kirikae, T., Schade, F. U., Zahringer, U., Kirikae, F., Brade, H., Kusumoto, S., Kusama, T., and Rietschel, E. T. TITLE: The significance of the hydrophilic backbone and the hydrophobic fatty acid regions of lipid A for macrophage binding and cytokine induction PubMed ID:8156049 JOURNAL: FEMS Immunol Med Microbiol. VOLUME: 8 PAGE: 13-26(1994)
<< Ref.2013 >> AUTHOR: Kusama, T., Soga, T., Shioya, E., Nakayama, K., Nakajima, H., Osada, Y., Ono, Y., Kusumoto, S., and Shiba, T. TITLE: Synthesis and antitumor activity of lipid A analogs having a phosphonooxyethyl group with alpha- or beta-configuration at position 1 PubMed ID:2092933 JOURNAL: Chem Pharm Bull (Tokyo). VOLUME: 38 PAGE: 3366-3372(1990)
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a-carboxymethyl analogue of biosynthetic precursor of lipid A from Eschericha coli 2-Deoxy-6-O-[2-deoxy-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-b-D-glucopyranosyl]-3-O-[(R)-3-hydroxytetradecanoyl]-2-[(R)-3-hydroxytetradecanoylamino]-a-D-glucopyranosyl-oxyacetic Acid CLS2014LipopolysaccharideShoichi Kusumoto#CM-406 C96H179N2O24P 1776.421Download ChemDraw structure data << Ref. 2015>> << Ref.2015 >> AUTHOR: Fukase,K., Oikawa,M., Suda,Y., Liu,W.C., Fukase,Y., Shintaku,T., Sekljic,H., Yoshizaki,H. and Kusumoto,S. TITLE: New Synthesis and Conformational analysis of Lipid A: biological activity and supramolecular assembly. JOURNAL: J. Endotoxin Res. VOLUME: 5 PAGE: 46 -51 (1999)
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Lipid A from Helicobactor pylori strain 206-1 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate CLS2015LipopolysaccharideShoichi Kusumoto C68H132N3O17P 1294.759Download ChemDraw structure dataIL-6 induction, TNF-a induction, Limulus activity ED50; << Ref. 2018>> 1H NMR; << Ref. 2016/2018>> ESI-MS (negative) m/z 1293.0 [(M-H)-]; << Ref. 2016/2018>> Helicobacter pylori strain 206-1 << Ref. 2017>> << Ref.2016 >> AUTHOR: Suda,Y., Ogawa,T., Kashihara,W., Oikawa,M., Shimoyama,T., Hayashi,T., Tamura,T. and Kusumoto,S. TITLE: Chemical Structure of Lipid A from Helicobacter Pylori Strain 206-1 Lipopolysaccharide. PubMed ID:9354387 JOURNAL: J. Biochem. VOLUME: 121 PAGE: 1129 -1133 (1997)
<< Ref.2017 >> AUTHOR: Sakai,Y., Oikawa,M., Yoshizaki,H., Ogawa,T., Suda,Y., Fukase,K. and Kusumoto,S. TITLE: Synthesis of Helicobacter pylori Lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group. JOURNAL: Tetrahedron Lett. VOLUME: 41 PAGE: 6843 -6847 (2000)
<< Ref.2018 >> AUTHOR: Suda,Y., Kim,Y.M., Ogawa,T., Yasui,N., Haegawa,Y., Kashihara,W., Shimoyama,T., Aoyama,K., Nagata,K., Tamura,T. and Kusumoto,S. TITLE: Chemical structure and biological activity of a Lipid A Compornent from Helicobacter pylori strain 206. PubMed ID:11521089 JOURNAL: J. Endotoxin Res. VOLUME: 7 PAGE: 95 -104 (2001)
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analogue of Lipid A from Helicobactor pylori strain 206-1 without ethanolamine 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-Phosphate CLS2016LipopolysaccharideShoichi Kusumoto C66H127N2O17P 1251.692Download ChemDraw structure data 1H NMR; << Ref. 2017>> << Ref. 2017>> << Ref. 2015>> << Ref.2015 >> AUTHOR: Fukase,K., Oikawa,M., Suda,Y., Liu,W.C., Fukase,Y., Shintaku,T., Sekljic,H., Yoshizaki,H. and Kusumoto,S. TITLE: New Synthesis and Conformational analysis of Lipid A: biological activity and supramolecular assembly. JOURNAL: J. Endotoxin Res. VOLUME: 5 PAGE: 46 -51 (1999)
<< Ref.2017 >> AUTHOR: Sakai,Y., Oikawa,M., Yoshizaki,H., Ogawa,T., Suda,Y., Fukase,K. and Kusumoto,S. TITLE: Synthesis of Helicobacter pylori Lipid A and its analogue using p-(trifluoromethyl)benzyl protecting group. JOURNAL: Tetrahedron Lett. VOLUME: 41 PAGE: 6843 -6847 (2000)
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Lipid A from Helicobactor pylori strain 206 tetra-acyl type 2-Deoxy-6-O-[2-deoxy-2-[(R)-3-(octadecanoyloxy)octadecanoylamino]-b-D-glucopyranosyl]-3-O-(R)-3-hydroxyhexadecanoyl-2-[(R)-3-hydroxyoctadecanoylamino]-a-D-glucopyranose 1-(2-Aminoethyl)phosphate CLS2017LipopolysaccharideShoichi Kusumoto#206-2 C84H162N3O19P 1549.168Download ChemDraw structure dataIL-6 induction, TNF-a induction, Lethal toxicity LD50, Limulus activity; << Ref. 2018>>