Pre-organization induced synthesis of a crossed alkene-bridged nisin Z DE-ring mimic by ring-closing metathesis

Chemical Communications

Volumn , Issue 2, 2005, Pages 192-194

  Ghalit, Nourdin ^a   Rijkers, Dirk T S ^a   Kemmink, Johan ^a   Versluis, Cees ^b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ANTIBIOTIC AGENT; NISIN; NISIN Z; SULFIDE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; CROSS LINKING; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS;

EID: 12744277997     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415555f     Document Type: Article

References (26)

1. Recent examples of our investigations include: (a) Leu-enkephalin: J. F. Reichwein, B. Wels, J. A. W. Kruijtzer, C. Versluis and R. M. J. Liskamp, Angew. Chem., Int. Ed., 1999, 38, 3684;
2. (b) Grb2 SH2 ligands: F. J. Dekker, N. J. de Mol, M. J. E. Fischer, J. Kemmink and R. M. J. Liskamp, Org. Biomol. Chem., 2003, 1, 3297;
3. (c) MC4-receptor ligands: B. Wels, PhD Thesis, University of Utrecht, 2004;
4. (d) B. Wels, J. A. W. Kruijtzer, K. M. Garner, W. A. J. Nijenhuis, W. H. Gispen, R. A. H. Adan and R. M. J. Liskamp, manuscript in preparation;
5. (e) vancomycin: H. T. ten Brink, D. T. S. Rijkers, J. Kemmink, H. W. Hilbers and R. M. J. Liskamp, Org. Biomol. Chem., 2004, 2, 2658.
6. (a) G. Jung, Angew. Chem., Int. Ed. Engl., 1991, 30, 1051;
7. (b) H.-G. Sahl, R. W. Jack and G. Bierbaum, Eur. J. Biochem., 1995, 230, 827.
8. For reviews on alkene metathesis: (a) T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18;
9. (b) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3012;
10. (c) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413.
11. Synthesis of the natural DE-ring: (a) K. Fukase, Y. Oda, A. Kubo, T. Wakamiya and T. Shiba, Bull. Chem. Soc. Jpn., 1990, 63, 1758;
12. total synthesis of nisin: (b) K. Fukase, M. Kitazawa, A. Sano, K. Shimbo, H. Fujita, S. Horimoto, T. Wakaiya and T. Shiba, Tetrahedron Lett., 1988, 29, 795;
13. (c) K. Fukase, M. Kitazawa, A. Gano, K. Shimbo, S. Horimoto, H. Fujita, A. Kubo, T. Wakamiya and T. Shiba, Bull. Chem. Soc. Jpn., 1992, 65, 2227.
14. (a) P. L. Toogood, Tetrahedron Lett., 1993, 34, 7833;
15. (b) S. Burrage, T. Rayham, G. Williams, J. W. Essex, C. Allen, M. Cardino, V. Swali and M. Bradley, Chem. Eur. J., 2000, 6, 1455;
16. (c) N. M. Okeley, Y. Zhu and W. A. van der Donk, Org. Lett., 2000, 2, 3603;
17. (d) H. Zhou and W. A. van der Donk, Org. Lett., 2002, 4, 1335;
18. (e) Y. Zhu, M. D. Gieselman, H. Zhou, O. Averin and W. A. van der Donk, Org. Biomol. Chem., 2003, 1, 3304;
19. (f) M. Matteucci, G. Bhalay and M. Bradley, Tetrahedron Lett., 2004, 45, 1399.
20. For recent examples of an alkene-bridge as a mimic of a disulfide bond see: S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; R. M. Williams and J. Liu, J. Org. Chem., 1998, 63, 2130; Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133; J. L. Stymiest, B. F. Mitchell, S. Wong and J. C. Vederas, Org. Lett., 2003, 5, 47.
21. For recent examples of an alkene-bridge as a mimic of a disulfide bond see: S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; R. M. Williams and J. Liu, J. Org. Chem., 1998, 63, 2130; Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133; J. L. Stymiest, B. F. Mitchell, S. Wong and J. C. Vederas, Org. Lett., 2003, 5, 47.
22. For recent examples of an alkene-bridge as a mimic of a disulfide bond see: S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; R. M. Williams and J. Liu, J. Org. Chem., 1998, 63, 2130; Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133; J. L. Stymiest, B. F. Mitchell, S. Wong and J. C. Vederas, Org. Lett., 2003, 5, 47.
23. For recent examples of an alkene-bridge as a mimic of a disulfide bond see: S. J. Miller, H. E. Blackwell and R. H. Grubbs, J. Am. Chem. Soc., 1996, 118, 9606; R. M. Williams and J. Liu, J. Org. Chem., 1998, 63, 2130; Y. Gao, P. Lane-Bell and J. C. Vederas, J. Org. Chem., 1998, 63, 2133; J. L. Stymiest, B. F. Mitchell, S. Wong and J. C. Vederas, Org. Lett., 2003, 5, 47.
24. -1 of the E/Z conformers: 3: 263.3/249.3, 4: 238.6/243.0, 5: 295.6/278.8, 6: 286.9/264.8. These values were obtained using MacroModel: F. Mohamadi, N. C. J. Richards, W. C. Guida, R. Liskamp, C. Caufield, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.
25. For a review on cross metathesis: S. J. Connon and S. Blechert, Angew. Chem., Int. Ed., 2003, 42, 1900.
26. J. T. Lundquist, IV and J. C. Pelletier, Org. Lett., 2001, 3, 781.