- Synthesis of 6-Hydroxysphingosine and α-Hydroxy Ceramide Using a Cross-Metathesis Strategy
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(Chemical Equation Presented) In this paper, a new synthetic route toward 6-hydroxysphingosine and α-hydroxy ceramide is described. The synthesis employs a cross-metathesis to unite a sphingosine head allylic alcohol with a long-chain fatty acid alkene that also bears an allylic alcohol group. To allow for a productive CM coupling, the sphingosine head allylic alcohol was protected with a cyclic carbonate moiety and a reactive CM catalyst system, consisting of Grubbs II catalyst and CuI, was employed.
- Wisse, Patrick,De Geus, Mark A. R.,Cross, Gen,Van Den Nieuwendijk, Adrianus M. C. H.,Van Rooden, Eva J.,Van Den Berg, Richard J. B. H. N.,Aerts, Johannes M. F. G.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.,Overkleeft, Herman S.
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p. 7258 - 7265
(2015/07/27)
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- Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements
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(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(i)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cereb
- Black, Fiona J.,Kocienski, Philip J.
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supporting information; experimental part
p. 1188 - 1193
(2010/06/15)
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- Enantioselective α-hydroperoxylation of long-chain fatty acids with crude enzyme of marine green alga Ulva pertusa
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When palmitic acid was incubated with crude enzyme of marine green alga Ulva pertusa, (R)-2-hydroperoxyhexadecanoic acid was formed in high enantiomeric purity (>99%ee).
- Akakabe,Matsui,Kajiwara
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p. 1137 - 1140
(2007/10/03)
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- Synthesis of optically active α-hydroxy acids by kinetic resolution through lipase-catalyzed enantioselective acetylation
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The lipase-catalyzed acetylation of a broad spectrum of racemic 2-hydroxy acids 1 to their 2-acetoxy acids 2 was shown to proceed with high enantioselectivity. Thus, the microbial lipases, in particular from Candida antarctica and Burkholderia species, are convenient biocatalysts for the synthesis of optically active 2-hydroxy acids in excellent enantioselectivity (ee values up to 99%). The absolute configurations of the 2-hydroxy acids 1 were assigned by comparison of the gas-chromatographic data with that of literature-known reference compounds, or by means of the exciton-coupled circular dichroism method (ECCD) on their bichromophoric 2-naphthoate 9-anthrylmethyl derivatives 3. These results establish that (S)-2-hydroxy acids 1 were preferentially acetylated by microbial lipases.
- Adam, Waldemar,Lazarus, Michael,Schmerder, Alexandra,Humpf, Hans-Ulrich,Saha-M?ller, Chantu R.,Schreier, Peter
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p. 2013 - 2018
(2007/10/03)
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- Enantioselective α hydroxylation of carboxylic acids with molecular oxygen catalyzed by the α oxidation enzyme system of young pea leaves (Pisum sativum): A substrate selectivity study
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The substrate selectivity of the α oxidation of carboxylic acids 1 by crude homogenate of young pea leaves was investigated. Saturated fatty acids with 7 to 16 carbon atoms and oleic acid were transformed to the enantiomerically pure (R)-2-hydroxy acids 2 in the presence of molecular oxygen.
- Adam, Waldemar,Lazarus, Michael,Saha-Moeller, Chantu R.,Schreier, Peter
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p. 2287 - 2292
(2007/10/03)
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- Cerebrosides from Fomitopsis pinicola (Sw. Ex Fr.) Karst.
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A cerebroside fraction was obtained from the bruit bodies of fomitopsis pinicola using column chromatography and then separated into six compounds by reversed-phase HPLC.The sugar component of all cerebrosides was D-glucose.The major fatty acids were 2-hydroxyfatty acids (C14-C18), the long chain base was identified as 9-methyl-C18-4,8-sphingadienine which is widely distributed in fungi and reported to be essential for the fruit-inducing activity of fungi.Based on degradation studies, fast atom bombardment mass spectrometry, and different 1H and 13C NMR investigations, the structure of the main cerebroside (1) was determined to be (4E,8E,2S,3R,2'R)-N-2'-hydroxypalmityl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine. - Keywords: Cerebroside; Glycolipid; Fomitopsis pinicola; 1H and 13C NMR
- Striegler, S.,Haslinger, E.
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p. 755 - 762
(2007/10/03)
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- Sphingolipids and glycerolipids. IV. Syntheses and ionophoretic activities of several analogues of soya-cerebroside II, a calcium ionophoretic sphingoglycolipid isolated from soybean
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For examination of the structure-activity relationship five analogues [(2'R)-2'-hydroxypalmitoyl (3), palmitoyl (4), (2'S)-2'-hydroxypalmitoyl (5), β-D-galactosyl (6), and 8,9-dihydro (7) relevancies] of soya-cerebroside II (2), which is a calcium ionopho
- Shibuya,Kurosu,Minagawa,Katayama,Kitagawa
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p. 1534 - 1544
(2007/10/02)
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- SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-9-METHYL-4,8-SPHINGADIENINE, THE CERAMIDE PORTION OF THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE, AND ITS (2R,3S)-ISOMER
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A synthesis of the natural enantiomer as well as its diastereomer of the title compound was accomplished, confirming the structure proposed for the fruiting-inducing cerebroside of Schizophyllum commune.
- Mori, Kenji,Funaki, Yuji
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p. 2369 - 2378
(2007/10/02)
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- SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-1-O-β-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE, THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE
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The title compound was synthesized by employing (R)-2-aminohexadecanoic acid, D-glucose and (S)-serine as the chiral sources, and the synthetic sample was found to be chemically and biologically identical with the fruiting-inducing cerebroside isolated fr
- Mori, Kenji,Funaki, Yuji
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p. 2379 - 2386
(2007/10/02)
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