Synthesis and spectroscopic characterization of enantiopure protected trans-4-amino-1-oxyl-2,2,6,6-tetramethyl piperidine-3-carboxylic acid (trans β-TOAC)

Tetrahedron Letters

Volumn 46, Issue 33, 2005, Pages 5573-5576

  Wright, Karen ^a   Castries, Augustin De ^a   Sarciaux, Matthieu ^a   Formaggio, Fernando ^b   Toniolo, Claudio ^b   Toffoletti, Antonio ^b   Wakselman, Michel ^a   Mazaleyrat, Jean Paul ^a  

^a LABORATOIRE DES SCIENCES DU CLIMAT ET DE L ENVIRONNEMENT   (France)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Chiral nitroxides; Modified amino acids; Spin labelled amino acids; trans TOAC

Indexed keywords

3 CARBOXYMETHYL 1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDONE; 4 AMINO 1 OXYL 2,2,6,6 TETRAMETHYLPIPERIDINE 3 CARBOXYLIC ACID; ALPHA METHYLBENZYLAMINE; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; ENAMINE; ESTER DERIVATIVE; NITROXIDE; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE; RADICAL; SODIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIS ISOMER; DIASTEREOISOMER; ELECTRON SPIN RESONANCE; ENANTIOMER; HYDROGENOLYSIS; REDUCTION; SYNTHESIS; TRANS ISOMER;

EID: 22144443214     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.049     Document Type: Article

References (38)

1. O.H. Griffith, and A.S. Waggoner Acc. Chem. Res. 2 1969 17 24
2. J.F. Keana Chem. Rev. 78 1978 37 64
3. G.L. Millhauser Trends Biochem. Sci. 17 1992 448 452
4. L. Columbus, and W.L. Hubbell Trends Biochem. Sci. 27 2002 288 295
5. W. Jahnke ChemBioChem 3 2002 167 173
6. P. Franchi, M. Lucarini, and G.F. Pedulli Current Org. Chem. 8 2004 1831 1849
7. P. Hanson, G. Martinez, G. Milhauser, F. Formaggio, M. Crisma, C. Toniolo, and C. Vita J. Am. Chem. Soc. 118 1996 271 272
8. C. Toniolo, M. Crisma, and F. Formaggio Biopolymers 47 1998 153 158
9. C. Toniolo, F. Formaggio, M. Crisma, J.-P. Mazaleyrat, M. Wakselman, C. George, J. Deschamps, J.L. Flippen-Anderson, B. Pispisa, M. Venanzi, and A. Palleschi Chem. Eur. J. 5 1999 2254 2264
10. C. Corvaja, E. Sartori, A. Toffoletti, F. Formaggio, M. Crisma, C. Toniolo, J.P. Mazaleyrat, and M. Wakselman Chem. Eur. J. 6 2000 2775 2782
11. B. Pispisa, C. Mazzuca, A. Palleschi, L. Stella, M. Venanzi, M. Wakselman, J.-P. Mazaleyrat, M. Rainaldi, F. Formaggio, and C. Toniolo Chem. Eur. J. 9 2003 4084 4093
12. A.L.J. Beckwith, V.W. Bowry, and K.U. Ingold J. Am. Chem. Soc. 114 1992 4983 4992
13. V.W. Bowry, and K.U. Ingold J. Am. Chem. Soc. 114 1992 4992 4996
14. C.J. Hawker, A.W. Bosman, and E. Harth Chem. Rev. 101 2001 3661 3688
15. L.J. Berliner, V. Khramtsov, H. Fujii, and T.L. Clanton Free Radic. Biol. Med. 30 2001 489 499
16. W. Adam, C.R. Saha-Möller, and P.A. Ganeshpure Chem. Rev. 101 2001 3499 3548
17. R.A. Sheldon, I.W.C.E. Arends, G.-J. Ten Brink, and A. Dijksman Acc. Chem. Res. 35 2002 774 781
18. J.S. Arterburn Tetrahedron 57 2001 9765 9768
19. N. Naik, and R. Braslau Tetrahedron 54 1998 667 696
20. F. Formaggio, M. Bonchio, M. Crisma, C. Peggion, S. Mezzato, A. Polese, A. Barazza, S. Antonello, F. Maran, Q.B. Broxterman, B. Kaptein, J. Kamphuis, R.M. Vitale, M. Saviano, E. Benedetti, and C. Toniolo Chem. Eur. J. 8 2002 84 93
21. K. Wright, M. Crisma, C. Toniolo, R. Török, A. Péter, M. Wakselman, and J.-P. Mazaleyrat Tetrahedron Lett. 44 2003 3381 3384
22. A. Péter, R. Török, K. Wright, M. Wakselman, and J.-P. Mazaleyrat J. Chromatogr. A 1021 2003 1 10
23. D.H. Appella, L.A. Christianson, I.L. Karle, D.R. Powell, and S.H. Gellman J. Am. Chem. Soc. 118 1996 13071 13072
24. D.H. Appella, L.A. Christianson, I.L. Karle, D.R. Powell, and S.H. Gellman J. Am. Chem. Soc. 121 1999 6206 6212
25. M. Schinnerl, J.K. Murray, J.M. Langenhan, and S.H. Gellman Eur. J. Org. Chem. 2003 721 726
26. R.P. Cheng, S.H. Gellman, and W.F. DeGrado Chem. Rev. 101 2001 3219 3232
27. D.L. Steer, R.A. Lew, P. Perlmutter, A.I. Smith, and M.-I. Aguilar Curr. Med. Chem. 9 2002 811 822
28. D. Seebach, T. Kimmerlin, R. Sebesta, M.A. Campo, and A.K. Beck Tetrahedron 60 2004 7455 7506
29. R.P. Cheng Curr. Opin. Struct. Biol. 14 2004 512 520
30. D. Seebach, A.K. Beck, and D. Bierbaum J. Chem. Biodiv. 1 2004 1111 1239
31. D.F. Hook, P. Bindschädler, Y.R. Mahajan, R. Šebesta, P. Kast, and D. Seebach Chem. Biodiv. 2 2005 591 632
32. 11
33. A.J. Ozinskas, and A.M. Bobst Helv. Chim. Acta 63 1980 1407 1411
34. D. Xu, K. Prasad, O. Repic, and T.J. Blacklock Tetrahedron: Asymmetry 8 1997 1445 1451
35. 13C NMR, C,H,N analysis and/or ESI/MS). Further experimental details of syntheses will be given in a full account of this study. Optical rotations [ α ] 546 25 are as follows: (1′S,3R,4S)-3: -52 (c 0.27; MeOH). (1′R,3S,4R)-3: +48 (c 0.28; MeOH). (3R,4S)-4: -24 (c 0.1; MeOH). (3S,4R)-4: +24 (c 0.1; MeOH).
36. +.
37. L. Dulog, and W. Wang Liebigs Ann. Chem. 1992 301 303
38. The extent of oxidation of the intermediate hydroxylamine to the nitroxide was monitored by thin layer chromatography.