Sulfoximines in pseudopeptides

Tetrahedron Letters

Volumn 38, Issue 7, 1997, Pages 1169-1172

  Bolm, Carsten ^a,b   Kahmann, Jan D ^a   Moll, Guido ^a,b  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PSEUDOPEPTIDE; SULFOXIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE SYNTHESIS;

EID: 0031575567     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00001-4     Document Type: Article

References (55)

1. 1. New address: Institut für Organische Chemie der RWTH Aachen, Prof.-Pirlet Str. 1, D-52074 Aachen, Germany. FAX: (int.) 241 8888 391; e-mail: Carsten.Bolm@RWTH-Aachen.de
2. 2. Reviews on peptide mimetics: (a) Gante, J. Angew. Chem. 1994,106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
3. 2. Reviews on peptide mimetics: (a) Gante, J. Angew. Chem. 1994,106, 1780; Angew. Chem. Int. Ed. Engl. 1994, 33, 1699.
4. (b) Giannis, A.; Kolter, T. ibid. 1993, 105, 1303; 1993, 32, 1244.
5. (b) Giannis, A.; Kolter, T. ibid. 1993, 105, 1303; 1993, 32, 1244.
6. (c) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994,113, 1.
7. (d) Adang, A. E. P.; Hermkens, P. H. H.; Linders, J. T. M.; Ottenheijm, H. C. J.; van Staveren, C. J. ibid. 1994, 113, 63.
8. (e) Wiley, R. A.; Rich, D. H. Med. Res. Rev. 1993, 13, 326.
9. 3. For other sulfur-containing pseudopeptides and peptide isosteres see: (a) Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. 1994, 106, 2181; Angew. Chem. Int. Ed. Engl. 1994, 33, 2067.
10. 3. For other sulfur-containing pseudopeptides and peptide isosteres see: (a) Gennari, C.; Salom, B.; Potenza, D.; Williams, A. Angew. Chem. 1994, 106, 2181; Angew. Chem. Int. Ed. Engl. 1994, 33, 2067.
11. (b) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. ibid. 1995, 107, 1892; 1995, 34, 1763.
12. (b) Gennari, C.; Nestler, H. P.; Salom, B.; Still, W. C. ibid. 1995, 107, 1892; 1995, 34, 1763.
13. (c) ibid. 1995, 107, 1894; 1995, 34, 1765.
14. (c) ibid. 1995, 107, 1894; 1995, 34, 1765.
15. (d) Sommerfeld, T. L.; Seebach, D. ibid. 1995, 107, 622; 1995, 34, 552.
16. (d) Sommerfeld, T. L.; Seebach, D. ibid. 1995, 107, 622; 1995, 34, 552.
17. (e) Moree, W. J.; van Gent, L. C.; van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron 1993, 49, 1133.
18. (f) Paik, S.; White, E. H. Tetrahedron Lett. 1996, 37, 4663.
19. (g) Moree, W. J.; van der Marel, G. A.; Liskamp, R. J. J. Org. Chem. 1995, 60, 5157 and references therein.
20. 4. Reviews on sulfoximines: (a) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
21. (b) Johnson, C. R. Acc. Chem. Res. 1973, 6, 341.
22. (c) Johnson, C. R. in Comprehensive Organic Chemistry; Vol. 3, (Eds,: Barton, D.; Ollis, W. D.) Pergamon Press, Oxford 1979, p. 223.
23. (d) Payne, S. G. Sulfur Reports 1992, 12, 57.
24. 5. Substituted β-carboxy sulfoximines have been used as transition-state analogue inhibitors of carboxypeptidase A: (a) Mock, W. L.; Zhang, J. Z. J. Biol. Chem. 1991, 266, 6393.
25. (b) Mock, W. L.; Tsay, J. -T. J. Am. Chem. Soc. 1989, 111, 4467.
26. (c) Mock, W. L.; Zhang, J. Z.; Ni, C. -Z.; Clardy, J. J. Org. Chem. 1990, 55, 5791.
27. 6. In β-hydroxy sulfoximines intramolecular hydrogen bonds involve the sulfoximine nitrogen, (a) Hwang, K. -J.; Logusch, E. W.; Brannigan, L. H.; Thompson, M. R. J. Org. Chem. 1987, 52, 3435.
28. (b) Felder, M. Dissertation at the University of Marburg, 1995.
29. 7. Both enantiomers of these sulfoximines can easily be obtained via resolution: (a) Fusco, R.; Tenconi, F. Chem. Ind. (Milan) 1965, 47, 61.
30. (b) Johnson, C. R.; Haake, M.; Schroeck, C. W. J. Am. Chem. Soc. 1970, 92, 6594.
31. (c) Johnson, C. R.; Schroeck, C. W. ibid. 1973, 95, 7418.
32. 8. An analogous procedure has been reported: Reggelin, M.; Dissertation at the University of Kiel, 1989.
33. 9. (a) Mander, L. N.; Sethi, P. Tetrahedron Lett. 1983, 24, 5425.
34. (b) See also: Aldrichim. Acta. 1987, 20, 53.
35. 10. Other α-sulfonimidoyl carboxy derivatives have been synthesized using various bases for deprotonation: (a) Hwang, K. -J. J. Org. Chem. 1986, 51, 99.
36. (b) Bolm, C.; Müller, J.; Zehnder, M.; Neuburger, M. A. Chem. Eur. J. 1995, 1, 312.
37. 11. In peptide couplings with pteroyl acid derivatives, S-alkylhomocysteine sulfoximines react predominantely at the amine nitrogen. The biological activity of the corresponding folic acid analogues has been studied. Harvison, P. J.; Kalman, T. I. J. Med. Chem. 1992, 35, 1227.
38. 12. (a) König, W.; Geiger, R. Chem. Ber. 1970, 103, 788.
39. (b) Bodanszky, M. Principles of Peptide Synthesis, Springer, Berlin 1993.
40. (c) Jones, J. Synthese von Aminosäuren und Peptiden, VCH, Weinheim 1996.
41. 13. Analogous to: (a) Schaffner-Sabba, K.; Tomaselli, H.; Henrici, B.; Renfroe, H. B. J. Org. Chem. 1977, 42, 952.
42. (b) Hwang, K. -J. ibid. 1986, 51, 99.
43. 2 giving a kind of β-lactam structure see: Williams, T. R.; Cram, D. J. J. Org. Chem. 1973, 38, 20.
44. 15. PyBOP = (Benzotriazol-1-yl-oxy)-tris-pyrrolidino-phosphonium-hexafluorophosphate, DIEA = Diisopropylethylamine. For the use of these reagents: Coste, J.; LeNguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
45. 16. The HOBt-methode gave no product.
46. 17. (a) Reviews: Seebach, D.; Beck, A. K.; Studer, A. in Modern Synthetic Methods 1995, Vol. 7, (Eds.: Ernst, B.; Leumann, C.) VCH, Weinheim 1995, 1.
47. (b) Seebach, D. Aldrichim. Acta 1992, 25, 59.
48. (c) Seebach, D. Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624.
49. (c) Seebach, D. Angew. Chem. 1988, 100, 1685; Angew. Chem. Int. Ed. Engl. 1988, 27, 1624.
50. 18. No racemization was observed under these conditions. This coupling can also be done with PyBOP/DIAE (86% yield). Use of DCC/DMAP gave about 17% of racemization (97% yield).
51. 19. Yields: 13a: 76%, 13b: 77%, 13c: 70% und 13d: 78%. The ammonium salts are thermolabile and tend to decarboxylate.
52. D = -4.6° (c = 1.04, acetone).
53. 21. Dessolin, M.; Guillerez, M. -G.; Thieriet, N.; Guibé, F.; Loffet, A. Tetrahedron Lett. 1995, 36, 5741.
54. 22. The acids 17a-c were purified by filtration of MTBE solutions through Celite. Traces of Pd remained in these samples.
55. 23. Chiral vinylogous sulfonamide-containing peptides show a preference for 12-and 14-membered H-bridged ring systems: Gennari, C.; Salom, B.; Potenza, D.; Longari, C.; Fioravanzo, E.; Carugo, O.; Sardone, N. Chem. Eur. J. 1996, 2, 644.