- Dihydroxylation of 2-vinylaziridine: Efficient synthesis of D-ribo-phytosphingosine
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An efficient and highly stereoselective synthesis of D-ribo-(2S,3S,4R)- phytosphingosine was accomplished in 62% overall yield starting from commercially available (2S)-hydroxymethylaziridine via osmium-catalyzed asymmetric dihydroxylation as a key step. The Royal Society of Chemistry.
- Yoon, Hyo Jae,Kim, Yong-Woo,Lee, Baeck Kyoung,Lee, Won Koo,Kim, Yongeun,Ha, Hyun-Joon
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Read Online
- Highly anti-selective dihydroxylation of 1,2-dialkyl substituted (Z)-allylic amines: stereoselective synthesis of a d-ribo-phytosphingosine derivative
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Protection of 1,2-dialkyl substituted (Z)-allylic amines with an N,N-diBoc group resulted in an opposite stereoselectivity in the OsO4-catalyzed dihydroxylation reactions to that of N-Boc-(Z)-allylic amines. A higher anti selectivity (>10:1) wa
- Jeon, Jongho,Shin, Moonyong,Yoo, Jae Won,Oh, Joon Seok,Bae, Jae Gwang,Jung, Seung Hwan,Kim, Young Gyu
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Read Online
- Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3
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The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.
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Paragraph 0093
(2015/03/31)
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- PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3
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The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.
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Page/Page column 70; 71
(2015/04/15)
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- Convenient synthesis of D- and L-xylo-1,2,3,4-alkane tetrols from a D-gluco-configured common building block
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D-gluco-Configured building block derived from d-(+)-gluconolactone has served as a common chiral template for the synthesis of enantiopure d- and l-xylo-configured 1,2,3,4-alkane tetrols. This has enabled synthesis of medicinally important guggultetrols and their enantiomers from a common starting point. Wittig and Grignard reactions are the key steps used for the incorporation of lipophilic chain.
- Borkar, Santosh Ramdas,Manjunath, Beedimane Narayana,Balasubramaniam, Sivaraman,Aidhen, Indrapal Singh
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- Structure-based discovery of glycolipids for CD1d-mediated NKT cell activation: Tuning the adjuvant versus immunosuppression activity
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Introduction of an aromatic group into the fatty acyl chain of α-GalCer modulates the activity and selectivity of IFN-γ/IL-4 secretion through CD1d-mediated activation of NKT cells. Compound 14-16 are more potent than α-Galcer and biased for IFN-γ than fo
- Fujio, Masakazu,Wu, Douglass,Garcia-Navarro, Raquel,Ho, David D.,Tsuji, Moriya,Wong, Chi-Huey
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p. 9022 - 9023
(2007/10/03)
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- Use of synthetic glycolipids as universal adjuvants for vaccines against cancer and infectious diseases
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The present invention relates to methods and compositions for augmenting an immunogenicity of an antigen in a mammal, comprising administering said antigen together with an adjuvant composition that includes a synthetic glycolipid compound of Formula I, a
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Page/Page column 19
(2008/06/13)
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- SYNTHETIC C-GLYCOLIPID AND ITS USE FOR TREATING CANCER INFECTIOUS DISEASES AND AUTOIMMUNE DISEASES
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The invention is directed to compounds of formula (I) wherein X is O, OR NH; R' is a hydrocarbon chain; R and are hydrogen, OH or a monosaccharide; R is hydrogen or a monosaccharide; Q' is optionally present and may be a C1-10 hydrocarbon; X' i
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- Phytosphingosines - A facile synthesis and spectroscopic protocol for configurational assignment
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A facile synthesis of four of the eight configurational isomers of phytosphingosine has been performed by employing Wittig and Julia olefination followed by Sharpless dihydroxylation. The set of these four stereoisomers served as model compounds for developing general chemical/CD/NMR protocols for assigning relative and absolute configurations of all phytosphingosine isomers. The procedure is based on a two-step derivatization to 2-N- naphthimide-1,3,4-0-trinaphthoate derivatives which gives rise to unique exciton coupled circular dichroic and 'H-NMR spectra in selected solvents. The spectra can be used as reference data for assignment of relative as well as absolute configurations of phytosphingosine isomers and congeners at the low-nanomole level.
- Shirota, Osamu,Nakanishi, Koji,Berova, Nina
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p. 13643 - 13658
(2007/10/03)
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- Chemoenzymatic synthesis of (+)-docosa-4,15-dien-l-yn-3-ol, a component of the marine sponge Cribrochalina vasculum, and confirmation of the structure, and absolute configuration of the acetylenic alcohol, by lipase-catalysed biotransformations
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The (4E,15Z)-, and (4£,15£)-isomers of (+)-docosa-4,15-dien-l-yn-3-ol 1, isolated from the marine sponge Cribroclialina vasculwn, were synthesized in highly enantiomerically pure form by lipase-mediated biotransformation with Novozym 435, and the structur
- Morishita, Kiyoshi,Kamezawa, Makoto,Ohtani, Takehiko,Tachibana, Hojun,Kawase, Mayumi,Kishimoto, Midori,Naoshima, Yoshinobu
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p. 513 - 518
(2007/10/03)
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- Synthesis of optically pure 4-alkenyl- or 4-alkanyl-2-hydroxytetronic acids
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The present invention relates to a method for synthesis of optically pure 4-alkenyl or 4-alkanyl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of pla
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- Optically pure 4-alkenyl- or 4-alkanyl-2-hydroxytetronic acids and pharmaceutical use thereof
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The present invention relates to a method for synthesis of optically pure 4-alkenyl or 4-alkanyl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of pla
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- Structure-activity relationship of α-galactosylceramides against b16- bearing mice
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Agelasphin-9b, (2S,3S,4R)-1-O-(α-D-galactopyranosyl)-16-methyl-2-[N- ((R)-2-hydroxytetracosanoyl)-amino]-1,3,4-heptadecanetriol, is a potent antitumor agent isolated from the marine sponge Agelas mauritianus. Various analogues of agelasphin-9b (a lead compound) were synthesized, and the relationship between their structures and biological activities was examined using several assay systems. From the results, KRN7000, (2S,3S,4R)-1-O-(α- D-galactopyranosyl)-2-(N-hexacosanoylamino)-1,3,4-octadecanetriol, was selected as a candidate for clinical application.
- Morita,Motoki,Akimoto,Natori,Sakai,Sawa,Yamaji,Koezuka,Kobayashi,Fukushima
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p. 2176 - 2187
(2007/10/02)
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- Branched Long Chain Alkyl Methyl Ethers: A New Class of Lipids from Spider Silk
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Long chain methyl branched 1-methoxyalkanes, a new class of ether lipids, have been identified from silk of the spider Linyphia triangularis (Araneae: Linyphiidae) by use of gas chromatographic retention indices, GC/MS investigations, and chemical modifications.Methyl groups are predominantly located at C-2, and ω-3 or ω-2 positions, respectively.Chain length varies between C24 and C32.The synthesis of representative compounds is reported.
- Schulz, Stefan,Toft, Soeren
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p. 6805 - 6820
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF LONG-CHAIN 3-n-ALKYLTHIOPHENES AND 3-n-ALKYLFURANS
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The syntheses of 3-substituted long-chain furans and thiophenes by a Wittig reaction are described. 1H-NMR and UV data of these compounds are reported.
- Shabana, R.,Amer, Adel,Mark, H. B.,Zimmer, Hans
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p. 299 - 306
(2007/10/02)
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- CHEMISTRY OF AYURVEDIC CRUDE DRUGS - VII GUGGULU (RESIN FROM COMMIPHORA MUKUL) - 6 ABSOLUTE STEREOCHEMISTRY OF GUGGULTETROLS
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With a view to elucidating the stereochemistry of guggultetrols, components of saponified Commiphora mukul resin, D-lyxo-, L-ribo-, and L-xylo-octadecane-1,2,3,4-tetrols have been synthesised by two different routes.One method starts with D-glyceraldehyde
- Kumar, Vijay,Dev, Sukh
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p. 5933 - 5948
(2007/10/02)
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