Concise and stereoselective synthesis of 2,5- and 2,4-disubstituted thiazole amino acid subunits for synthesizing thiazole-containing peptides |
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Authors: | Takuji Magata Yoshimi Hirokawa Yusuke Moriguchi Ryosuke Yokoi Shotaro Nojiri Ryota Miyazaki Sayuri Akasako Rina Takahashi Munetaka Nishida Junya Hakoda Ryota Nakayama Aya Tanaka Naoyoshi Maezaki |
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Affiliation: | Faculty of Pharmacy, Osaka Ohtani University, 3-11-1 Nishikiori-Kita, Tondabayashi, Osaka 584-8540, Japan |
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Abstract: | A concise, highly stereoselective synthesis of 2,4- and 2,5-disubstituted thiazole amino acids was developed. These are important building blocks for various biologically active thiazole-containing natural peptides and their regioisomeric analogues. The fundamental reactions are diastereoselective addition of (4- or 5-bromothiazol-2-yl)lithium to N-tert-butanesulfinyl imine with subsequent Pd-catalyzed phenoxycarbonylation. |
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Keywords: | 2,4- and 2,5-disubstituted thiazole amino acid units Subunit for thiopeptides Pd-catalyzed phenoxycarbonylation |
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