Prediction and determination of the stereochemistry of the 1,3,5-trimethyl-substituted alkyl chain in verucopeptin, a microbial metabolite

Journal of Organic Chemistry

Volumn 79, Issue 15, 2014, Pages 6858-6867

  Yoshimura, Aya ^a   Kishimoto, Shinji ^a   Nishimura, Shinichi ^a   Otsuka, Saori ^a   Sakai, Yuki ^a   Hattori, Akira ^a   Kakeya, Hideaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; FATTY ACIDS; METABOLITES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STEREOSELECTIVITY;

ABSOLUTE STEREOCHEMISTRY; DIASTEREOMERS; LIPOPEPTIDES; MICROBIAL METABOLITES; NMR SPECTRUM; OXIDATIVE CLEAVAGES; SIMPLE APPROACH; STREPTOMYCES SP;

FORECASTING;

2,4,6 TRIMETHYL CARBOXYLIC ACID; 2,4,6 TRIMETHYLOCTANOIC ACID DERIVATIVE; CARBENE; CARBOXYLIC ACID; FATTY ACID DERIVATIVE; LIPOPEPTIDE; PROTON; UNCLASSIFIED DRUG; VERUCOPEPTIN; DEPSIPEPTIDE; FATTY ACID;

ARTICLE; DIASTEREOISOMER; DRUG DEGRADATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; OXIDATIVE STRESS; PREDICTION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

CARBOXYLIC ACIDS; DEPSIPEPTIDES; FATTY ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84905386237     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo500906v     Document Type: Article

References (21)

1. Feher, M.; Schmidt, J. M. J. Chem. Inf. Comput. Sci. 2003, 43, 218
2. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311
3. Bifulco, G.; Dambruoso, P.; Gomez-Paloma, L.; Riccio, R. Chem. Rev. 2007, 107, 3744
4. Matsumori, N.; Kaneno, D.; Murata, M.; Nakamura, H.; Tachibana, K. J. Org. Chem. 1999, 64, 866
5. Murata, M.; Matsuoka, S.; Matsumori, N.; Paul, G. K.; Tachibana, K. J. Am. Chem. Soc. 1999, 121, 870
6. Lee, J.; Kobayashi, Y.; Tezuka, K.; Kishi, Y. Org. Lett. 1999, 1, 2181
7. Kobayashi, Y.; Lee, J.; Tezuka, K.; Kishi, Y. Org. Lett. 1999, 1, 2177
8. Higashibayashi, S.; Czechtizky, W.; Kobayashi, Y.; Kishi, Y. J. Am. Chem. Soc. 2003, 125, 14379
9. Akiyama, K.; Kawamoto, S.; Fujimoto, H.; Ishibashi, M. Tetrahedron Lett. 2003, 44, 8427
10. Schmidt, Y.; Breit, B. Org. Lett. 2010, 12, 2218
11. Schmidt, Y.; Lehr, K.; Colas, L.; Breit, B. Chem. Eur. J. 2012, 18, 7071
12. Stahl, M.; Schopfer, U.; Frenking, G.; Hoffmann, R. W. J. Org. Chem. 1996, 61, 8083
13. Kishimoto, S.; Tsunematsu, Y.; Nishimura, S.; Hayashi, Y.; Hattori, A.; Kakeya, H. Tetrahedron 2012, 68, 5572
14. Motohashi, K.; Toda, T.; Sue, M.; Furihata, K.; Shizuri, Y.; Matsuo, Y.; Kasai, H.; Shin-Ya, K.; Takagi, M.; Izumikawa, M.; Horikawa, Y.; Seto, H. J. Antibiot. 2010, 63, 549
15. Nishiyama, Y.; Sugawara, K.; Tomita, K.; Yamamoto, H.; Kamei, H.; Oki, T. J. Antibiot. 1993, 46, 921
16. Sugawara, K.; Toda, S.; Moriyama, T.; Konishi, M.; Oki, T. J. Antibiot. 1993, 46, 928
17. Stahl, M.; Schopfer, U.; Frenking, G.; Hoffmann, R. W. Mol. Phys. 1997, 92, 569
18. Evans, D. A.; Dow, R. L.; Shih, T. L.; Takacs, J. M.; Zahler, R. J. Am. Chem. Soc. 1990, 112, 5290
19. Xaio, J.; Kumazawa, S.; Yoshikawa, N.; Mikawa, T.; Sato, Y. J. Antibiot. 1993, 46, 48
20. Lin, Z.; Flores, M.; Forteza, I.; Henriksen, N. M.; Concepcion, G. P.; Rosenberg, G.; Haygood, M. G.; Olivera, B. M.; Light, A. R.; Cheatham, T. E., 3rd; Schmidt, E. W. J. Nat. Prod. 2012, 75, 644
21. Tsantrizos, Y. S.; Shen, J. H.; Trimble, L. A. Tetrahedron Lett. 1997, 38, 7033