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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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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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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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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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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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