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Registros recuperados: 18
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Efficient synthesis of 3-trifluoromethylphenyldiazirinyl oleic acid derivatives and Their biological activity for protein kinase C OAK
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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光アフィニティーラベルによるポストゲノム解析 OAK
橋本 , 誠; Hashimoto, Makoto.
Ano: 2006 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/2082
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Practical conditions for photoaffinity labeling with 3-trifluoromethyl-3-phenyldiazirine photophore OAK
Hashimoto, Makoto; Hatanaka, Yasumaru.
Palavras-chave: PHENYLALANINE; DIAZIRINE; LIGAND.
Ano: 2006 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/732
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Positively coded photoaffinity label for altering isoelectric points of proteins OAK
Hashimoto, Makoto; Hatanaka, Yasumaru.
Novel diazirinyl photoaffinity ligand, which contains (3-trifluoromethyl) phenyldiazirine and penta(epsilon-Boc-Lys) as a photoreactive code, allows the introduction of a positive cascade to alter the pI value of labeled components, facilitating the isolation of photolabeled biocomponents with isoelectric focusing techniques. (c) 2006 Elsevier Ltd. All rights reserved.
Palavras-chave: Photoaffinity labeling; Diazirine; Isoelectric focusing; Biotin.
Ano: 2006 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/1321
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Asymmetric and efficient synthesis of homophenylalanine derivatives via Friedel-Crafts reaction with trifluoromethanesulfonic acid OAK
Murashige, Ryo; Hayashi, Yuka; Hashimoto, Makoto; 橋本, 誠.
An efficient Friedel-Crafts reaction of TFA-Asp(Cl)-OMe and stoichiometric amounts of benzene was established by using neat trifluoromethanesulfonic acid (TfOH) as solvent and catalyst under a mild condition. This methodology has been applied to many aromatic compounds and enabled synthesis of several homophenylalanine derivatives.
Ano: 2008 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/2703
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Recent progress in diazirine based photoaffinity labeling OAK
Hashimoto, Makoto; Hatanaka, Yasumaru; 橋本, 誠.
Based on the recent development of molecular biology, the investigation of biofunctional machinery at their ligand accepting interface has become one of the challenging and important subject of post-genome field. The technique of photoaffinity labeling has become increasingly appreciated as a powerful methodology for the purpose. This micro review focused synthesis of trifluoromethylphenyldiazirine, which is one of the most promising photophore, and its application to the biomolecules.
Palavras-chave: Photoaffinity labeling; Chemical biology; Bioorganic chemistry; Structure-activity relationships; Diazirine.
Ano: 2008 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/2700
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Simple synthesis of deuterium and 13C labeled trifluoromethyl phenyldiazirine derivatives as stable isotope tags for mass spectrometry OAK
Hatanaka, Yasumaru; Hashimoto, Makoto.
日本薬学会Chemical & pharmaceutical bulletin 52(11)p.185-1386より転載
Palavras-chave: Diazirine; Photoaffinity label; Stable isotope.
Ano: 2004 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/127
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Stereoselective synthesis of (E)- and (Z)-β-bromostyrene containing trifluoromethyldiazirine for photoaffinity labeling OAK
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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DIOL DERIVATIVE OF (3-TRIFLUOROMETHYL)PHENYLDIAZIRINE FOR POST-LABELING OF PHOTOCROSSLINK OAK
Hashimoto, Makoto; Hatanaka, Yasumaru.
3-Trifluoromethylphenyldiazirinylated diol derivative was utilized to introduce an aldehyde by periodate oxidation, followed by the formation of a Schiff base with biotin hydrazide on a PVDF membrane for post-labeling of photocrosslinked proteins. The biotin hydrazide was able to post-label the 2.5 x 10-13 mole of closslinked component for chemiluminescent visualization.
Ano: 2005 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/735
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Enzyme cleavable and biotinylated photoaffinity ligand with diazirine OAK
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
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Simple method for the introduction of iodo-label on (3-trifluoromethyl) phenyldiazirine for photoaffinity labeling OAK
Hashimoto, Makoto; Kato, Yuhi; Hatanaka, Yasumaru.
A simple and mild method was developed for the introduction of iodo-label on (3-trifluoromethyl) phenyidiazirine (TPD) aromatic ring in the presence of three membered diazirine ring. An iodination protocol, I-2-BTI in CH3CN, was found to be effective even though affinity ligands are pre-installed.
Palavras-chave: HIGH SPECIFIC RADIOACTIVITY; CARBENE-GENERATING REAGENT; IODINATION METHOD; PROBES; DERIVATIVES; DIAZIRINE; EFFICIENT; ACID; PHOTOPHORE; PROTEINS.
Ano: 2006 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/733
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A novel biotinylated diazirinyl ceramide analogue for photoaffinity labeling OAK
Hashimoto, Makoto; Hatanaka, Yasumaru; 橋本, 誠.
A novel photoreactive ceramide analogue, which contains (3-trifluoromethyl) phenyldiazirinyl lipid and biotinylated sphingosine, was synthesized. The probe was recognized as an antigen by anti-ceramide antibody and as a substrate for sphingolipid ceramide N-deacylase. These results indicate that the probe may be useful as a photoaffinity-biotinylating agent in sphingolipid studies.
Ano: 2008 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/2704
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Synthesis of tag introducible (3-trifluoromethyl)phenyldiazirine based photoreactive phenylalanine OAK
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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Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide OAK
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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蛋白質、ペプチドの新規修飾法 OAK
橋本, 誠; Hashimoto, Makoto.
Palavras-chave: ペプチド; 化学修飾; 機能解析.
Ano: 2008 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/2039
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Post-biotinylation of Photocrosslinking by Staudinger-Bertozzi Ligation of Preinstalled Alkylazide Tag OAK
Hashimoto, Makoto; Hatanaka, Yasumaru.
Post-biotinylation of the alkyl azide derivative of trifluoromethyl phenyldiazirine (TPD) was elucidated to apply a photoaffinity biotinylation technique. A photo-modified polyvinilidene difluoride (PVDF) membrane was used as a photolabeled component and we introduced biotin by Staudinger-Bertozzi ligation. The 15 pmol amount of biotinylated reagent was still effective for the visualization of cross-linked product on the matrix. The results show the potential utility of alkyl azide carrying TPD derivatives in the application of photoaffinity biotinylation, which could be useful for the ligands with tight structural requirements.
Palavras-chave: Diazirine; Photoaffinity label; Chemical biology; Staudinger reaction; Avidin-biotin.
Ano: 2005 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/832
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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 OAK
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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Improvement in the Properties of 3-Phenyl-3-trifluoromethyldiazirine Based Photoreactive Bis-Glucose Probes for GLUT4 Following Substitution on the Phenyl Ring OAK
Hashimoto, Makoto; Yang, Jing; Hatanaka, Yasumaru; Sadakane, Yutaka; Nakagomi, Kazuya; Holman, Geoffrey David.
日本薬学会Chemical & pharmaceutical bulletin 50(7) p.1004-1006より転載
Palavras-chave: Photoaffinity label; Diazirine; Glucose transporter.
Ano: 2002 URL: http://ir.obihiro.ac.jp/dspace/handle/10322/332
Registros recuperados: 18
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