Synthetic Studies of plusbacin A3
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- Katsuyama Akira
- 北大院薬
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- Matsuda Akira
- 北大院薬
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- Ichikawa Satoshi
- 北大院薬
Bibliographic Information
- Other Title
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- Joullie-Ugi反応を用いたplusbacin A3の合成研究
Abstract
<p>Plusbacin A3, which was isolated from Pseudomonas sp. PB-6250 obtained from a soil sample collected in the Okinawa Prefecture, Japan, has five nonproteinogenic amino acids, allo-D-threonine, trans-3-hydroxy-L-proline, L-threo-b-hydroxy-aspartic acid, and D-threo-b-hydroxy-aspartic acid. Plusbacin A3 exhibits a potent antibacterial activity against drug-resistant pathogens including Methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE). Since the mode of action of plusbacin A3 differs from existing antibacterial drug, plusbacin A3is expected to be a lead compound as a novel antibacterial drug.</p><p>We planned to synthesize plusbain A3considering to develop more convergent synthetic route, which can be applicable to structure-activity relationship. Our retro-synthetic analysis of plusbacin A3 is depicted as follows. Segment A was synthesized from isocyanide 14, imine 2, and carboxylic acid 15, and segment B was synthesized from isocyanide 13 imine 2, and carboxylic acid 12 via Joullie-Ugi reaction. Then, esterification of segment A and segment B afford trace amount of cyclization precursor 34. </p>
Journal
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- Symposium on the Chemistry of Natural Products, symposium papers
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Symposium on the Chemistry of Natural Products, symposium papers 56 (0), Poster52-, 2014
Symposium on the Chemistry of Natural Products Steering Committee
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Details 詳細情報について
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- CRID
- 1390282763021770496
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- NII Article ID
- 130007399556
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- ISSN
- 24331856
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- Text Lang
- ja
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- Data Source
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- JaLC
- CiNii Articles
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- Abstract License Flag
- Disallowed