Synthesis, resolution and assignment of absolute configuration of trans 3-amino-1-oxyl-2,2,5,5-tetramethylpyrrolidine-4-carboxylic acid (POAC), a cyclic, spin-labelled β-amino acid

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4416-4426

  Wright, Karen ^a   Dutot, Laurence ^a   Wakselman, Michel ^a   Mazaleyrat, Jean Paul ^a   Crisma, Marco ^b   Formaggio, Fernando ^b   Toniolo, Claudio ^b  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

^b CNR   (Italy)

Author keywords

Amino acids; Binaphthol esters; Chiral nitroxides; Circular dichroism; POAC; Resolution; Spin labelled amino acids

Indexed keywords

3 AMINO 1 OXYL 2,2,5,5 TETRAMETHYLPYRROLIDINE 4 CARBOXYLIC ACID; BETA AMINO ACID; CARBOXYLIC ACID DERIVATIVE; DIPEPTIDE DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; DIASTEREOISOMER; ESTERIFICATION; PRIORITY JOURNAL; SAPONIFICATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 41549128353     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.058     Document Type: Article

References (74)

1. Griffith O.H., and Waggoner A.S. Acc. Chem. Res. 2 (1969) 17-24
2. Keana J.F. Chem. Rev. 78 (1978) 37-64
3. Millhauser G.L. Trends Biochem. Sci. 17 (1992) 448-452
4. Columbus L., and Hubbell W.L. Trends Biochem. Sci. 27 (2002) 288-295
5. Beckwith A.L.J., Bowry V.W., and Ingold K.U. J. Am. Chem. Soc. 114 (1992) 4983-4992
6. Bowry V.W., and Ingold K.U. J. Am. Chem. Soc. 114 (1992) 4992-4996
7. Hawker C.J., Bosman A.W., and Harth E. Chem. Rev. 101 (2001) 3661-3688
8. Adam W., Saha-Möller C.R., and Ganeshpure P.A. Chem. Rev. 101 (2001) 3499-3548
9. Sheldon R.A., Arends I.W.C.E., Ten Brink G.-J., and Dijksman A. Acc. Chem. Res. 35 (2002) 774-781
10. Naik N., and Braslau R. Tetrahedron 54 (1998) 667-696
11. Formaggio F., Bonchio M., Crisma M., Peggion C., Mezzato S., Polese A., Barazza A., Antonello S., Maran F., Broxterman Q.B., Kaptein B., Kamphuis J., Vitale R.M., Saviano M., Benedetti E., and Toniolo C. Chem.-Eur. J. 8 (2002) 84-93
12. Krishna M., DeGraff W., Hankovszky O., Sár C., Kàlai T., Jekö J., Russo A., Mitchell J., and Hideg K. J. Med. Chem. 41 (1998) 3477-3492
13. Brasch R., London D., Wesbey G., Tozer T., Nitecki D., Williams R., Doemeny J., Dallas Tuck L., and Lallemand D. Radiology 147 (1983) 773-779
14. Winalski C., Shortkroff S., Mulkern R., Schneider E., and Rosen G. Magn. Reson. Med. 48 (2002) 965-972
15. Lex L., Hideg K., and Hankovszky H.O. Can. J. Chem. 60 (1982) 1448-1451
16. Hideg K., and Hankovszky H.O. In: Berliner L.J., and Reuben J. (Eds). Biological Magnetic Resonance. Spin Labelling Theory and Applications Vol. 8 (1989), Plenum, New York, NY 427-488
17. Hideg K., Cseko{combining double acute accent} J., Hankovszky H.O., and Sohár P. Can. J. Chem. 64 (1986) 1482-1490
18. Rassat A., and Rey P. Bull. Soc. Chim. Fr. 3 (1967) 815-817
19. Nakaie C.R., Goissis G., Schreier S., and Paiva A.C.M. Braz. J. Med. Biol. Res. 14 (1981) 173-180
20. Seidemann R., and Dulog L. Makromol. Chem. 187 (1986) 2545-2551
21. Balog M., Kálai T., Jeko{combining double acute accent} J., Berente Z., Steinhoff H.-J., Engelhard M., and Hideg K. Tetrahedron Lett. 44 (2003) 9213-9217
22. Preliminary reports of part of this work have been published:
23. Wright K., Formaggio F., Toniolo C., Török R., Péter A., Wakselman M., and Mazaleyrat J.-P. Tetrahedron Lett. 44 (2003) 4183-4186
24. Péter A., Török R., Wright K., Wakselman M., and Mazaleyrat J.-P. J. Chromatogr., A 1021 (2003) 1-10
25. Wright K., De la Croix de Castries A., Sarciaux M., Wakselman M., Mazaleyrat J.-P., Török R., Péter A., Crisma M., Formaggio F., and Toniolo C. In: Flegel M., Fridkin M., Gilon C., and Slaninova J. (Eds). Peptides 2004 (2005), Kenes International, Geneva, Switzerland 1047-1048
26. Wright K., Crisma M., Toniolo C., Török R., Péter A., Wakselman M., and Mazaleyrat J.-P. Tetrahedron Lett. 44 (2003) 3381-3384
27. Wright K., De Castries A., Sarciaux M., Formaggio F., Toniolo C., Toffoletti A., Wakselman M., and Mazaleyrat J.-P. Tetrahedron Lett. 46 (2005) 5573-5576
28. Wright K., Sarciaux M., De Castries A., Wakselman M., Mazaleyrat J.-P., Toffoletti A., Corvaja C., Crisma M., Peggion C., Formaggio F., and Toniolo C. Eur. J. Org. Chem. (2007) 3133-3144
29. Hideg K., Hankovszky H.O., Halász H.A., and Sohár P. J. Chem. Soc., Perkin Trans. 1 (1986) 1482-1490
30. Marchetto R., Schreier S., and Nakaie C.R. J. Am. Chem. Soc. 115 (1993) 11042-11043
31. Toniolo C., Valente E., Formaggio F., Crisma M., Pilloni G., Corvaja C., Toffoletti A., Martinez G.V., Hanson M.P., Millhauser G.L., George C., and Flippen-Anderson J.L. J. Pept. Sci. 1 (1995) 45-47
32. Toniolo C., Crisma M., and Formaggio F. Biopolymers 47 (1998) 153-158
33. Martin L., Ivancich A., Vita C., Formaggio F., and Toniolo C. J. Pept. Res. 58 (2001) 424-432
34. Hanson P., Millhauser G., Formaggio F., Crisma M., and Toniolo C. J. Am. Chem. Soc. 118 (1996) 7618-7625
35. Toniolo C., Formaggio F., Crisma M., Mazaleyrat J.-P., Wakselman M., George C., Deschamps J., Flippen-Anderson J.L., Pispisa B., Venanzi M., and Palleschi A. Chem.-Eur. J. 5 (1999) 2254-2264
36. Corvaja C., Sartori E., Toffoletti A., Formaggio F., Crisma M., Toniolo C., Mazaleyrat J.-P., and Wakselman M. Chem.-Eur. J. 6 (2000) 2775-2782
37. Pispisa B., Mazzuca C., Palleschi A., Stella L., Venanzi M., Wakselman M., Mazaleyrat J.-P., Rainaldi M., Formaggio F., and Toniolo C. Chem.-Eur. J. 9 (2003) 4084-4093
38. Iverson B.L. Nature 385 (1997) 113-115
39. Seebach D., and Matthews J.L. Chem. Commun. (1997) 2015-2022
40. Cheng R.P., Gellman S.H., and DeGrado W.F. Chem. Rev. 101 (2001) 3219-3232
41. Seebach D., Beck A.K., and Bierbaum D.J. Chem. Biodivers. 1 (2004) 1111-1239
42. Hook D.F., Bindschädler P., Mahajan Y.R., Šebesta R., Kast P., and Seebach D. Chem. Biodivers. 2 (2005) 591-632
43. Seebach D., Hook D., and Glättli A. Biopolymers (Pept. Sci.) 84 (2006) 23-27
44. Tominaga M., Barbosa S.R., Poletti E.F., Zukerman-Schpector J., Marchetto R., Schreier S., Paiva A.C.M., and Nakaie C.R. Chem. Pharm. Bull. 49 (2001) 1027-1029
45. Nakaie C.R., Silva E.G., Cilli E.M., Marchetto R., Schreier S., Paiva T.B., and Paiva A.C.M. Peptides 23 (2002) 65-70
46. Mazaleyrat J.-P., Wright K., Gaucher A., Toulemonde N., Wakselman M., Oancea S., Peggion C., Formaggio F., Setnička V., Keiderling T.A., and Toniolo C. J. Am. Chem. Soc. 126 (2004) 12874-12879
47. Mazaleyrat J.-P., Wright K., Gaucher A., Toulemonde N., Dutot L., Wakselman M., Broxterman Q.B., Kaptein B., Oancea S., Peggion C., Crisma M., Formaggio F., and Toniolo C. Chem.-Eur. J. 11 (2005) 6921-6929
48. Dutot L., Gaucher A., Wright K., Wakselman M., Mazaleyrat J.-P., Peggion C., Formaggio F., and Toniolo C. Tetrahedron: Asymmetry 17 (2006) 363-371
49. Dutot L., Gaucher A., Wright K., Wakselman M., Mazaleyrat J.-P., Peggion C., Formaggio F., and Toniolo C. In: Rolka K., Rekowski P., and Silberring J. (Eds). Peptides 2006 (2007), Kenes International, Geneva, Switzerland 76-77
50. Wright, K.; Dutot, L.; Gaucher, A.; Wakselman, M.; Mazaleyrat, J.-P.; Peggion, C.; Formaggio, F.; Toniolo, C. Peptides for Youth, Del Valle, S., Escher, E., Lubell, W. D., Eds.; Springer: Secaucus, NJ, in press;
51. Dutot, L.; Wright, K.; Gaucher, A.; Wakselman, M.; Mazaleyrat, J.-P.; Peggion, C.; Formaggio, F.; Toniolo, C. J. Am. Chem. Soc., in press.
52. Rozantzev E.G., and Krinitzkaya L.A. Tetrahedron 21 (1965) 491-499
53. Rauckman E.J., Rosen G.M., and Abou-Donia M.B. Synth. Commun. 17 (1975) 409-413
54. Ozinskas A.J., and Bobst A.M. Helv. Chim. Acta 63 (1980) 1407-1411
55. Barrett G.C. In: Barrett G.C. (Ed). Chemistry and Biochemistry of the Amino Acids (1985), Chapman and Hall, London, UK 338-354
56. Lee J., Kim K.R., Won S., Kim J.H., and Goto J. Analyst 126 (2001) 2128-2133
57. Fuji K., Yang X.-S., Ohnishi H., Hao X.-J., Obata Y., and Tanaka K. Tetrahedron: Asymmetry 10 (1999) 3243-3248
58. Panchal B.M., Einhorn C., and Einhorn J. Tetrahedron Lett. 43 (2002) 9245-9248
59. Diastereoselective alkylation of a Schiff base of binaphthyl glycinate has also been reported:. Tanaka K., Ahn M., Watanabe Y., and Fuji K. Tetrahedron: Asymmetry 7 (1996) 1771-1782
60. Chen S.-T., Hsiao S.-C., Chang C.-H., and Wang K.-T. Synth. Commun. 22 (1992) 391-398
61. Breipohl G., Knolle J., Langner D., O'Malley G., and Uhlmann E. Bioorg. Med. Chem. Lett. 6 (1996) 665-670
62. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397-4398
63. Mazaleyrat J.-P., Gaucher A., Šavrda J., and Wakselman M. Tetrahedron: Asymmetry 8 (1997) 619-631
64. Formaggio F., Crisma M., Toniolo C., Tchertanov L., Guilhem J., Mazaleyrat J.-P., Gaucher A., and Wakselman M. Tetrahedron 56 (2000) 8721-8734
65. Suzuki H. Electronic Absorption Spectra and Geometry of Organic Molecules (1967), Academic, New York, NY
66. Mislow K., Glass M.A.W., O'Brien R.E., Rutkin P., Steinberg D.H., Weiss J., and Djerassi C. J. Am. Chem. Soc. 84 (1962) 1455-1478
67. Mislow K., Bunnenberg E., Records R., Wellman K., and Djerassi C. J. Am. Chem. Soc. 85 (1963) 1342-1349
68. Loncar-Tomascovic L., Sarac-Arneri R., Hergold-Brundic A., Nagl A., Mintas M., and Sandström J. Helv. Chim. Acta 83 (2000) 479-494
69. α-tetrasubstituted α-amino acids, see:. Formaggio F., Broxterman Q.B., and Toniolo C. In: Goodman M., Felix A., Moroder L., and Toniolo C. (Eds). Houben-Weyl: Methods of Organic Chemistry. Synthesis of Peptides and Peptidomimetics Vol. E 22c (2003), Thieme, Stuttgart 292-310
70. Bui T.T.T., Formaggio F., Crisma M., Monaco V., Toniolo C., Hussain R., and Siligardi G. J. Chem. Soc., Perkin Trans. 2 (2000) 1043-1046
71. 2/cyclohexane solvent mixture. CCDC 674101 contains the supplementary crystallographic data for this structure. These data can be obtained free of charge at htpp://www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB21EZ, UK; fax: (internat.) +44 1223/336 033; e-mail: deposit@ccdc.cam.ac.uk].
72. Broda M.A., Mazur L., Koziol A.E., and Rzeszotarska B. J. Pept. Sci. 10 (2004) 448-461
73. Carpino L.A., Imazumi H., El-Faham A., Ferrer F.J., Zhang C., Lee Y., Foxman B.M., Henklein P., Hanay C., Mügge C., Wenschuh H., Klose J., Beyermann M., and Bienert M. Angew. Chem., Int. Ed. 41 (2002) 441-445
74. Angew. Chem. 114 (2002) 457-461