1-Aminoxymethylcyclopropanecarboxylic acid as building block of β N-O turn and helix: Synthesis and conformational analysis in solution and in the solid state

Tetrahedron

Volumn 66, Issue 51, 2010, Pages 9733-9737

  Chang, Xiao Wei ^a   Han, Qing Chuan ^a   Jiao, Zhi Gang ^a   Weng, Lin Hong ^a   Zhang, Dan Wei ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

N O turn; 2,2 aminoxy acid; Cyclopropane side chain; Secondary structure

Indexed keywords

1 AMINOXYMETHYLCYCLOPROPANECARBOXYLIC ACID; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; NITROGEN; OLIGOPEPTIDE; OXYGEN; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID STATE; SOLUTION AND SOLUBILITY; X RAY CRYSTALLOGRAPHY;

EID: 78650181688     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.10.037     Document Type: Article

References (47)

1. For selected reviews:
2. S.H. Gellman Acc. Chem. Res. 31 1998 173 180
3. A.J. Souers, and J.A. Ellman Tetrahedron 57 2001 7431 7448
4. R.P. Cheng, S.H. Gellman, and W. DeGrado Chem. Rev. 101 2001 3219 3232
5. F. Brackmann, and A. de Meijere Chem. Rev. 107 2007 4493 4537
6. X. Li, Y.-D. Wu, and D. Yang Acc. Chem. Res. 41 2008 1428 1438
7. D. Seebach, and J. Gardiner Acc. Chem. Res. 41 2008 1366 1375
8. Y.S. Tsantrizos Acc. Chem. Res. 41 2008 1252 1263
9. M.C. Pirrung Acc. Chem. Res. 32 1999 711 718
10. J. Salaun Top. Curr. Chem. 207 2000 1 67
11. H. Zhao Drug Discovery Today 12 2007 149 155
12. S.K. Ner, C.J. Suckling, A.R. Bell, and R. Wrigglesworthbt J. Chem. Soc., Chem. Commun. 1987 480 482
13. I. MacInnes, D. Schorstein, C.J. Suckling, and R. Wrigglesworth J. Chem. Soc., Perkin Trans. 1 1983 2771 2776
14. R.J. Breckenridge, and C.J. Suckling Tetrahedron 42 1986 5665 5677
15. J. Rancourt, D.R. Cameron, V. Gorys, D. Lamarre, M. Poirier, D. Thibeault, and M. Llinas-Brunet J. Med. Chem. 47 2004 2511 2522
16. For example employing cyclopropane ring constraint in α-peptides, see:
17. K. Burgess, W. Li, D. Lim, and D. Moye-Sherman Biopolymers 42 1997 439 453
18. K. Burgess, K.-K. Ho, and B.M. Pettitt J. Am. Chem. Soc. 116 1994 799 800
19. K. Burgess, K.-K. Ho, and B.M. Pettitt J. Am. Chem. Soc. 117 1995 54 65
20. K. Burgess, K.-K. Ho, and B. Pal J. Am. Chem. Soc. 117 1995 3808 3819
21. K. Burgess, and C.-Y. Ke J. Org. Chem. 61 1996 8627 8631
22. D. Seebach, S. Abele, T. Sifferlen, M. Hänggi, S. Gruner, and P. Seiler Helv. Chim. Acta 81 1998 2218 2243
23. S. Abele, P. Seiler, and D. Seebach Helv. Chim. Acta 82 1999 1559 1571
24. S. Abele, and D. Seebach Eur. J. Org. Chem. 2000 1 15
25. D. Seebach, A.K. Beck, and D.J. Bierbaum Chem. Biodiver. 1 2004 1111 1239
26. G. Lelais, and D. Seebach Biopolymers 76 2004 206 243
27. X. Li, and D. Yang Chem. Commun. 32 2006 3367 3379 and references cited therein
28. D. Yang, Y.-H. Zhang, B. Li, D.-W. Zhang, J.C.-Y. Chan, N.-Y. Zhu, S.-W. Luo, and Y.-D. Wu J. Am. Chem. Soc. 126 2004 6956 6966
29. D. Yang, Y.-H. Zhang, and N.-Y. Zhu J. Am. Chem. Soc. 124 2002 9966 9967
30. D. Yang, D.-W. Zhang, Y. Hao, Y.-D. Wu, S.-W. Luo, and N.-Y. Zhu Angew. Chem., Int. Ed. 43 2004 6719 6722
31. D. Yang, X.-W. Chang, D.-W. Zhang, Z.-F. Jiang, K.-S. Song, Y.-H. Zhang, N.-Y. Zhu, L.-H. Weng, and M.-Q. Chen J. Org. Chem. 75 2010 4796 4805
32. P. Langer Angew. Chem., Int. Ed. 39 2000 3049 3052
33. C.Z. Yu, B. Liu, and L.Q. Hu J. Org. Chem. 66 2001 5413 5418
34. H. Huang, X.C. Liu, M. Qiu, Z. Zheng, and J. Deng Org. Lett. 8 2006 3359 3364
35. O. Mitsunobu Synthesis 1981 1 28
36. A. Rodriguez, I. Pina, L. Acosta, C. Ramirz, and J. Soto J. Org. Chem. 66 2001 648 658
37. T. Fuchikami, Y. Shibata, and Y. Suzuki Tetrahedron Lett. 27 1986 3173 3176
38. D. Yang, B. Li, F.-F. Ng, Y.-L. Yan, J. Qu, and Y.-D. Wu J. Org. Chem. 66 2001 7303 7312
39. I. Shin, M.R. Lee, J. Lee, M. Jung, W. Lee, and J. Yoon J. Org. Chem. 65 2000 7667 7675
40. C. Rodríguez-García, A. Oliva, R. Ortuño, and V. Branchadell J. Am. Chem. Soc. 123 2001 6157 6163
41. J. Roble, M. Cimarusti, L. Simpkins, B. Brown, D. Ryono, J. Bird, M. Asaad, T. Schaeffer, and N. Trippodo J. Med. Chem. 39 1996 494 502
42. J. Christoffers, T. Kauf, T. Werner, and M. Rossle Eur. J. Org. Chem. 2006 2601 2608
43. 3 at low concentration.
44. G.B. Liang, C.J. Rito, and S.H. Gellman J. Am. Chem. Soc. 114 1992 4440 4442
45. D. Yang, F.-F. Ng, Z.-J. Li, Y.-D. Wu, K.W.K. Chan, and D.-P. Wang J. Am. Chem. Soc. 118 1996 9794 9795
46. For details, please see the Supplementary data.
47. CCDC 795383 and 795384 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.