59(P28) Total Synthesis of Thiopeptide Antibiotic, Mirococcin P
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- Shin Chung-gi
- Faculty of Technology, Kanagawa University
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- Okumura Kazuo
- Faculty of Technology, Kanagawa University
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- Shigekuni Masashi
- Faculty of Technology, Kanagawa University
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- Ito Akinori
- Faculty of Technology, Kanagawa University
Bibliographic Information
- Other Title
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- 59(P28) チオペプチド系抗生物質ミクロコッシンPの全合成(ポスター発表の部)
Abstract
Micrococcin P (1), isolated from the culture of Bacillus pumilus, is a unique macrocyclic peptide. In addition, many similar antibiotic peptides have been also isolated from various kinds of strains. The peptide (1) include a characteristic main structure, 2,3,6-polythiazolesubstituted pyridine skeleton called Fragment A-C (11) composed of multisubstituted pyridine and thiazole-dehydropeptide moieties and two segments, Fragments B and D. First of all, the protected Fragment A-C segment (11) was synthesized from 3-cyano-6-dimethoxymethyl-2-pyridone via 2-bromoacetyl-3-(5-ethoxycarbonyl)-thiazole-6-dimethoxymethylpyridine(9) in twelve steps. Furthermore, the protected Fragment D (17) was obtained from N,O-Isop-Thr-OH (14) via the corresponding N,O-Isop-Thr-propanolamide (15) in four steps. On the other hand, the protected Fragment B (21) was also synthesized from N, O-diprotected Thr-[1- propen-1-yl]thiazole-4-carboxylate (18) in three steps. Finally, after the coupling of Fragment A-C (11) with Fragment D (17) and then Fragment B (21), the obtained linear precursor Fragment A-B-C-D of 1 was cyclized using BOP and deprotected with TBAF to give micrococcin 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 39 (0), 349-354, 1997
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
- 1390282681055519872
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- NII Article ID
- 110006679553
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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