Solid-phase unnatural peptide synthesis (UPS)

Journal of the American Chemical Society

Volumn 118, Issue 25, 1996, Pages 6070-6071

  O'Donnell, Martin J ^a   Zhou, Changyou ^a   Scott, William L ^b  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; PEPTIDE SYNTHESIS; TECHNIQUE;

EID: 0030057825     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9601245     Document Type: Article

References (39)

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20. α-C bond formation in protected peptides: reference 8, footnote 1. (a) Ager, D. J.; Froen, D. E.; Klix, R. C.; Zhi, B.; McIntosh, I. M.; Thangarasa, R. Tetrahedron 1994, 50, 1975-1982. (b) Steglich, W.; Jäger, M.; Jaroch, S.; Zistler, P. Pure Appl. Chem. 1994, 66, 2167-2170. (c) Kazmaier, U. J. Org. Chem. 1994, 59, 6667-6670. (d) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, 1995; Vol. 7, pp 1-178.
21. α-C bond formation in protected peptides: reference 8, footnote 1. (a) Ager, D. J.; Froen, D. E.; Klix, R. C.; Zhi, B.; McIntosh, I. M.; Thangarasa, R. Tetrahedron 1994, 50, 1975-1982. (b) Steglich, W.; Jäger, M.; Jaroch, S.; Zistler, P. Pure Appl. Chem. 1994, 66, 2167-2170. (c) Kazmaier, U. J. Org. Chem. 1994, 59, 6667-6670. (d) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, 1995; Vol. 7, pp 1-178.
22. α-C bond formation in protected peptides: reference 8, footnote 1. (a) Ager, D. J.; Froen, D. E.; Klix, R. C.; Zhi, B.; McIntosh, I. M.; Thangarasa, R. Tetrahedron 1994, 50, 1975-1982. (b) Steglich, W.; Jäger, M.; Jaroch, S.; Zistler, P. Pure Appl. Chem. 1994, 66, 2167-2170. (c) Kazmaier, U. J. Org. Chem. 1994, 59, 6667-6670. (d) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, 1995; Vol. 7, pp 1-178.
23. α-C bond formation in protected peptides: reference 8, footnote 1. (a) Ager, D. J.; Froen, D. E.; Klix, R. C.; Zhi, B.; McIntosh, I. M.; Thangarasa, R. Tetrahedron 1994, 50, 1975-1982. (b) Steglich, W.; Jäger, M.; Jaroch, S.; Zistler, P. Pure Appl. Chem. 1994, 66, 2167-2170. (c) Kazmaier, U. J. Org. Chem. 1994, 59, 6667-6670. (d) Seebach, D.; Beck, A. K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Weinheim, 1995; Vol. 7, pp 1-178.
24. O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-4518.
25. O'Donnell, M. J.; Burkholder, T. P.; Khau, V. V.; Roeske, R. W.; Tian, Z. Pol. J. Chem. 1994, 68, 2477-2488.
26. 2O, 5 h.
27. O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663-2666.
28. Other recent applications involving resin-bound imines: Murphy, M. M.; Schullek, J. R.; Gordon, E. M,; Gallop, M. A. J. Am. Chem. Soc. 1995, 117, 7029-7030.
29. 2CO - Phe - OMe with 4-bromobenzyl bromide showed that 15-68% racemization of the pre-existing chiral center was observed with potassium tert-butoxide, 9-lithium fluorene, or lithium 2,6-di-tert-butyl-4-methylphenoxide.
30. 4-t-Bu (Figure 3) resulted in overalkylation at the amide bond and extensive racemization. For other uses of "Schwesinger bases", see: Schwesinger, R.; Willaredt, J.; Schlemper, H.; Keller, M.; Schmidt, D.; Fritz, H. Chem. Ber. 1994, 127, 2435-2454.
31. (a) Seebach, D.; Hungerbühler, E.; Nafe, R.; Schnurrenberger, P.; Weidmann, B.; Züger, M. Synthesis 1982, 138-141.
32. (b) Rehwinkel, H.; Steglich, W. Synthesis 1982, 826-827.
33. (c) Oppolzer, W.; Lienard, P. Helv. Chim. Acta 1992, 75, 2572-2582.
34. Allyl esters in peptide synthesis: (a) Seitz, O.; Kunz, H. Angew, Chem., Int. Ed. Engl. 1995, 34, 803-805. (b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 3129-3132.
35. Allyl esters in peptide synthesis: (a) Seitz, O.; Kunz, H. Angew, Chem., Int. Ed. Engl. 1995, 34, 803-805. (b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Chastanet, J.; Zhu, J. Tetrahedron Lett. 1995, 36, 3129-3132.
36. 1H-NMR, and HRMS.
37. 2H·(D,L)-Phe - Leu: C, 52.04; H, 5.91; N, 7.14. Found: C, 49.90; H, 5.81; N, 7.04. Amino acid analysis: Phe/Gly = 97/3.
38. 1H-NMR.
39. Hydantoins 8 were prepared in 32-50% yields by solid-phase UPS followed by the Parke-Davis cyclization methodology, see: Dewitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad Sci. U.S.A. 1993, 90, 6909-6913. equation presented