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Registros recuperados: 7
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Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide 19
Hashimoto, Makoto; Hatanaka, Yasumaru; Nabeta, Kensuke.
A versatile synthesis of diazirine-based photoreactive fatty acid analogues is reported. The key step is phenoxy alkylation of diazirine with halo alkyl acid esters. The conditions described will be acceptable for the synthesis of various alkyl-length derivatives. The fatty acid derivatives are acceptors for reverse reactions of sphingolipid ceramide N-deacylase (SCDase), which catalyzes the condensation of psychosine and fatty acids to form photoreactive galactosylceramide. The photoreactive galactosylceramide can also be prepared with chemical synthesis, condensation of psychosine and fatty acid succinimidyl ester, and is recognized with anti-GarCer antibody both before and after irradiation.
Palavras-chave: DIAZIRINE.
Ano: 2002 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/736
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Effective synthesis of a carbon-linked diazirinyl fatty acid derivative via reduction of the carbonyl group to methylene with triethylsilane and trifluoroacetic acid 19
Hashimoto, Makoto; Hatanaka, Yasumaru; Nabeta, Kensuke.
Friedel-Crafts acylation of the aryldiazirine with omega-ester-alpha-acyl halide and successive reduction of the carbonyl group to methylene with triethylsilane and trifluoroacetic acid gave diazirinylated fatty acids.
Palavras-chave: ALDEHYDES; KETONES.
Ano: 2003 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/734
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Synthesis of tag introducible (3-trifluoromethyl)phenyldiazirine based photoreactive phenylalanine 19
Hashimoto, Makoto; Hatanaka, Yasumaru; Sadakane, Yutaka; Nabeta, Kensuke.
An efficient synthesis of tag introducible (3-trifluoromethyl)phenyldiazirine based phenylalanine derivatives is described. Alkylation of a chiral glycine equivalent with a spacer containing (3-trifluoromethyl)phenyldiazirinyl bromides enables us to create photoreactive L-phenylalanine derivatives. After introduction of biotin at the spacer, the biotinylated and photoreactive amino acid was applied for L-amino acid oxidase and incorporated into a substrate binding site. These compounds will be powerful tools not only for photoaffinity labeling to elucidate properties of bioactive peptides but also as trifunctional photophors to introduce a ligand skeleton. (C) 2002 Elsevier Science Ltd. All rights reserved.
Palavras-chave: FLAVIN BINDING-SITES; PHOTOAFFINITY; DIAZIRINE; IDENTIFICATION; PROTEINS; RECEPTOR; DOMAIN.
Ano: 2002 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/713
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オリーブ(Olea europea Linn.)中の揮発成分の分析 19
鍋田, 憲助; 松尾, 敏正; 杉沢, 博; Nabeta, Kensuke; Matsuo, Toshimasa; Sugisawa, Hiroshi.
Ano: 1988 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/1541
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Stereoselective synthesis of (E)- and (Z)-β-bromostyrene containing trifluoromethyldiazirine for photoaffinity labeling 19
Hashimoto, Makoto; Komano, Tomoko; Nabeta, Kensuke; Hatanaka, Yasumaru.
日本薬学会 Chemical & pharmaceutical bulletin 53(1)p.140-142より転載
Palavras-chave: Diazirine; Photoaffinity label; Stable isotope; Hydrogenolysis.
Ano: 2005 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/128
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Efficient synthesis of 3-trifluoromethylphenyldiazirinyl oleic acid derivatives and Their biological activity for protein kinase C 19
Hashimoto, Makoto; Nabeta, Kensuke; Murakami, Kentaro.
3-Trifluoromethylphenyldiazirine based oleic acids derivatives are synthesized to elucidate the functions of specific activation of protein kinase C (PKC) with oleic acid. The synthetic route is based on the alkylation of phenolic derivative with oleic acid equivalent and the post-functionalization. of the compound to achieve radiolabeling. Several compounds have biological activity for PKC with similar efficacy with that of oleic acid. The results indicated that the diaizinyl oleic acid derivatives should be useful to study the specific functions of oleic acid for PKC. (C) 2003 Elsevier Science Ltd. All rights reserved.
Palavras-chave: PHENYLALANINE; DIAZIRINE; RESPONSES; ANALOGS; PROBES.
Ano: 2003 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/1324
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Enzyme cleavable and biotinylated photoaffinity ligand with diazirine 19
Hashimoto, Makoto; Okamoto, Shun’ji; Nabeta, Kensuke; Hatanaka, Yasumaru.
The efficient synthesis of an enzyme cleavable biotinylated diazirinyl photoaffinity ligand is described to allow the effective manipulation of the photolabeled biocomponents. The compound contains a glutamic acid gamma-methyl ester, which is a precursor of the substrate for V8 protease, between the diazirinyl photophor and biotin moiety. After alkaline hydrolysis of the ester, the compound can be proteolyzed at the Glu moiety by V8 protease. The photophore was introduced to L-Phe p-nitroanilide and the ligand was applied to photolabel of chymotrypsin to manipulate the application of the concept.
Palavras-chave: Photoaffinity labeling; Diazirine; Avidin-biotin; V8 protease; Chymotrypsin.
Ano: 2004 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/738
Registros recuperados: 7
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