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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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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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