The 'azirine/oxazolone approac' to the synthesis of Aib-Pro endothiopeptides

Helvetica Chimica Acta

Volumn 91, Issue 8, 2008, Pages 1471-1488

  Budzowski, Artur ^a,b   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b JAGIELLONIAN UNIVERSITY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2 (BENZOYLAMINO) 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBOXYLIC ACID; 1 [2 [( 1 [(BENZYLOXY)CARBONYL]PYRROLIDINE 2 CARBONYL)AMINO] 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBOXYLIC ACID; 1 [2 METHYL 2 [(THIOBENZOYL)AMINO]PROPANOYL]PYRROLIDINE 2 CARBOXYLIC ACID; ACID ANHYDRIDE; AZIRINE DERIVATIVE; METHYL 1 [2 ([ 1 [2 ([ 1 [(BENZYLOXY)CARBONYL]PYRROLIDINE 2 CARBONYL]AMINO) 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBONYL]AMINO) 2 METHYLPROPANOYL]PYRROLIDINE 2 CARBOXYLATE; METHYL 1 [2 (BENZOYLAMINO) 2 METHYL 1 THIOXOPROPYL] PYRROLIDINE 2 CARBOXYLATE; METHYL 1 [2 [( 1 [2 (BENZOYLAMINO) 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBONYL) AMINO] 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBOXYLATE; METHYL 1 [2 [(1 [(BENZYLOXY)CARBONYL]PYRROLIDINE 2 CARBONYL)AMINO] 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBOXYLATE; METHYL 1 [2 METHYL 2 [(THIOBENZOYL)AMINO]PROPANOYL]PYRROLIDINE 2 CARBOXYLATE; METHYL 2 [[ 1 [2 ([ 1 [(BENZYLOXY)CARBONYL]PYRROLIDINE 2 CARBONYL]AMINO) 2 METHYL 1 THIOXOPROPYL]PYRROLIDINE 2 CARBONYL]AMINO] 3 PHENYLPROPIONATE; N,2 DIMETHYL 2 [( 1 [2 METHYL 2 [(THIOBENZOYL)AMINO]PROPANOYL]PYRROLIDINE 2 CARBONYL) AMINO] N PHENYLPROPANAMIDE; N,2 DIMETHYL 2 [( 1 [2 METHYL 2 [(THIOBENZOYL)AMINO]PROPANOYL]PYRROLIDINE 2 CARBONYL) AMINO] N PHENYLPROPANETHIOAMIDE; OXAZOLONE; PEPTIDE DERIVATIVE; PROLINE; THIOACID; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; EPIMER; EPIMERIZATION; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; ROOM TEMPERATURE; SAPONIFICATION; X RAY CRYSTALLOGRAPHY;

EID: 55449133359     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200890160     Document Type: Article

References (80)

1. 'Peptides: Chemistry and Biology', Eds. N. Sewald, H.-D. Jakubke, Wiley-VCH, Weinheim, 2002, pp. 339-378;
2. A. F. Spatola, in 'Chemistry and Biochemistry of Amino Acids, Peptides and Proteins', Ed. B. Weinstein, Marcel Dekker, New York, 1983, Vol. 7, pp. 267-375.
3. S. Vijayalakshmi, R. Balaji Rao, I. L. Karle, P. Balaram, Biopolymers 2000, 53, 84;
4. U. Slomczynska, D. D. Bensen, J. Zabrocki, K. Kociolek, A. Redlinski, F. Reusser, W. C. Hutton, M. T. Leplawy, G. R. Marshall, J. Am. Chem. Soc. 1992, 114, 4095.
5. C.-F. Chang, M. H. Zehfus, Biopolymers 1996, 40, 609;
6. J. Samanen, T. Cash, D. Narindray, E. Brandeis, W. Adams, H. Weideman, T. Yellin, J. Med. Chem. 1991, 34, 3036.
7. B. Vitoux, A. Aubry, M. T. Cung, M. Marraud, Int. J. Pept. Protein Res. 1986, 27, 617;
8. W. F. Degrado, Adv. Protein Chem. 1988, 39, 51.
9. J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243.
10. a) M. Schutkowski, M. Jakob, G. Landgraf, I. Born, K. Neubert, G. Fischer, Eur. J. Biochem. 1997, 245, 381;
11. b) D. Krumme, H. Tschesche, Tetrahedron 1999, 55, 3007;
12. c) B. Zacharie, M. Lagraoui, M. Dimarco, C. Penney, L. Gagnon, J. Med. Chem. 1999, 42, 2046.
13. H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
14. D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1981, 64, 482;
15. D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1987, 70, 102.
16. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1986, 69, 1153;
17. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1987, 70, 354;
18. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1988, 71, 140.
19. a) R. Luykx, C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527;
20. b) R. T. N. Luykx, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 4093.
21. R. A. Breitenmoser, T. R. Hirt, R. T. N. Luykx, H. Heimgartner, Helv. Chim. Acta 2001, 84, 972.
22. a) N. Pradeille, H. Heimgartner, J. Pept. Sci. 2003, 9, 827;
23. b) N. Pradeille, O. Zerbe, K. Möhle, A. Linden, H. Heimgartner, Chem. Biodivers. 2005, 2, 1127.
24. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13.
25. W. Altherr, A. Linden, H. Heimgartner, Chem. Biodivers. 2007, 4, 1144.
26. a) S. Stamm, H. Heimgartner, Eur. J. Org. Chem. 2004, 3820;
27. b) S. Stamm, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1;
28. c) S. Stamm, H. Heimgartner, Helv. Chim. Acta 2006, 89, 1841;
29. d) S. Stamm, H. Heimgartner, Tetrahedron 2006, 62, 9671.
30. J. Rizo, L. M. Gierasch, Annu. Rev. Biochem. 1992, 61, 38 7.
31. 'Topical Issue Peptaibiotics', Eds. C. Toniolo, H. Brückner, Chem. Biodivers. 2007, 4, pp. 1021-1412.
32. R. Nagaraj, P. Balaram, Tetrahedron 1981, 37, 1263.
33. B. F. Gisin, D. G. Davis, Z. K. Borowska, J. E. Hall, S. Kobayashi, J. Am. Chem. Soc. 1981, 103, 6373.
34. V. V. Suresh Babu, H. N. Gopi, Tetrahedron Lett. 1998, 39, 1049.
35. K. Akaji, Y. Tamai, Y. Kiso Tetrahedron Lett. 1995, 36, 9341.
36. M. Crisma, M. Anzolin, G. M. Bonora, C. Toniolo, E. Benedetti, B. Di Blasio, V. Pavone, M. Saviano, A. Lombardi, F. Nastri, C. Pedone, Gazz. Chim. Ital. 1992, 122, 239.
37. K. Clausen, M. Thorsen, S.-O. Lawesson, Tetrahedron 1981, 37, 3635;
38. M. Thorsen, B. Yde, U. Pedersen, K. Clausen, S.-O. Lawesson, Tetrahedron 1983, 39, 3429;
39. D. W. Brown, M. M. Campbell, C. V. Walker, Tetrahedron 1983, 39, 1075;
40. H. Ripperger, J. Prakt. Chem. 1987, 329, 1039;
41. S. F. Guziek Jr., L. M. Wasmund, J. Chem. Res., Synop. 1989, 155;
42. S. F. Guziek Jr., M. Wasmund, Tetrahedron Lett. 1990, 31, 23;
43. J. Jurayj, M. Cushman, Tetrahedron 1992, 48, 8601;
44. K. C. Nicolaou, B. S. Safina, M. Zak, S. H. Lee, M. Nevalainen, M. Bella, A. A. Estrada, C. Funke, F. J. Zecri, S. Bulat, J. Am. Chem. Soc. 2005, 127, 11159;
45. C. Giordano, G. Lucente, A. Masi, M. Paglialunga Paradisi, A. Sansone, S. Spisani, Amino Acids 2007, 33, 477.
46. K. Clausen, M. Thorsen, S.-O. Lawesson, A. F. Spatola, J. Chem. Soc., Perkin Trans. 1 1984, 78 5;
47. T. Hoeg-Jensen, C. E. Olsen, A. Holm, J. Org. Chem. 1994, 59, 1257;
48. T. Hoeg-Jensen, A. F. Spatola, A. Holm, Int. J. Pept. Protein Res. 1996, 47, 190;
49. K. Hartke, A. Barrmeyer, J. Prakt. Chem. 1996, 338, 251.
50. B. Zacharie, G. Sauve, C. Penney, Tetrahedron 1993, 49, 10489;
51. M. A. Shalaby, C. W. Grote, H. Rapoport, J. Org. Chem. 1996, 61, 9045;
52. C. T. Brain, A. Hallett, S. Y. Ko, J. Org. Chem. 1997, 62, 3808.
53. U. Kazmaier, S. Ackermann, Org. Biomol. Chem. 2005, 3, 3184.
54. a) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721;
55. b) J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 888;
56. c) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1999, 55, 5359;
57. d) J. Lehmann, H. Heimgartner, Helv. Chim. Acta 1999, 82, 1899.
58. a) R. A. Breitenmoser, H. Heimgartner, Helv. Chim. Acta 2001, 84, 786;
59. b) R. A. Breitenmoser, A. Linden, H. Heimgartner, Helv. Chim. Acta 2002, 85, 990.
60. S. V. Pansare, J. Vederas, J. Org. Chem. 1989, 54, 2311.
61. F. M. Arcamone, M. Altamura, E. Perrotta, A. Crea, S. Manzini, D. Poma, A. Salimbeni, A. Triolo, C. A. Maggi, J. Antibiot. 2000, 53, 1086.
62. A. Budzowski, A. Linden, H. Heimgartner, Heterocycles 2004, 64, 417.
63. M. A. McKervey, M. B. OBSullivan, P. L. Myers, R. H. Green, J. Chem. Soc., Chem. Commun. 1993, 94.
64. C. K. Johnson, 'ORTEP II', Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
65. J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
66. M. Blagoev, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 1458.
67. T. Jeremic, A. Linden, H. Heimgartner, Chem. Biodivers. 2004, 1, 1730.
68. J. M. Villalgordo, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2830.
69. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
70. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
71. R. H. Blessing, Acta Crystallogr., Sect. A 1995, 51, 33.
72. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
73. H. D. Flack, G. Bernardinelli, Acta Crystallogr., Sect. A 1999, 55, 908;
74. H. D. Flack, G. Bernardinelli, J. Appl. Crystallogr. 2000, 33, 1143.
75. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 6.1.1.1, p. 477;
76. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.6.8, p. 219;
77. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992 Vol. C, Table 4.2.4.3, p. 200.
78. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
79. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
80. G. M. Sheldrick, SHELXL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.