A general methodology for automated solid-phase synthesis of depsides and depsipeptides. Preparation of a valinomycin analogue

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8063-8075

  Kuisle, Oliver ^a   Quiñoá, Emilio ^a   Riguera, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DEPSIPEPTIDE; PEPTIDE DERIVATIVE; VALINOMYCIN DERIVATIVE;

AMINO ACID ANALYSIS; ARTICLE; AUTOMATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG SYNTHESIS; PEPTIDE ANALYSIS; PEPTIDE SYNTHESIS;

EID: 0344241060     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981580+     Document Type: Article

References (43)

1. Szostak, J. Chem. Rev. 1997, 97, 347-510.
2. For reviews covering the period from 1992 to 1997, see: Booth, S.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees. D. C. Tetrahedron 1998, 54, 15385-15443, and the previous review cited therein.
3. (a) Eckstein, F. Nucleotides and Analogues: A Practical Approach; Rickwood, D., Hames, B. D., Eds.; IRL Press: Oxford, 1991.
4. For a recent review, see: (b) Beaucage, S. L.; Radhakrishnan, P. I. Tetrahedron 1992, 48, 2223-2311.
5. For a review on earlier works in the field, see: Fréchet, J. M. J. Polymer-Supported Reactions in Organic Synthesis; Wiley: New York, 1980; Chapter 8, p 407.
6. For more recent examples, see: (a) Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491-493.
7. (b) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449-450.
8. Stewart, J. M.; Young, J. D. Solid-Phase Peptide Synthesis, 2nd ed.; Pierce Chemical Co.: Rockford, IL, 1984.
9. Dietrich, B.; Viout, P.; Lehn, J.-M. Macrocydic Chemistry; VCH: Weinheim, 1993.
10. Izatt, R. M.; Bradshaw, J. S.; Nielsen, S. A.; Lamb, J. D.; Christensen, J. J. Chem. Rev. 1986, 85, 271-339.
11. Fernández, R.; Rodriguez, J.; Quiñoá, E.; Riguera, R.; Muñoz, L.; Fernández-Suárez, M.; Debitus, C. J. Am. Chem. Soc. 1996, 118, 11635-11643.
12. Dell, A.; Williams, D. H.; Morris, H. R.; Smith, G. A.; Feeney, J.; Roberts, G. C. K. J. Am. Chem. Soc. 1975, 97, 2497-2506.
13. Adang, A. E. P.; Hermkens, P. H. H.; Linders, J. T. M.; Ottenheijm, H. C. J.; van Staveren, C. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 63-78.
14. (a) Seebach, D.; Ciceri, P. E.; Overhand, M.; Jaun, B.; Rigo, D. Helv. Chim. Acta 1996, 79, 2043-2066.
15. (b) Yang, J.; Gellman, S. H. J. Am. Chem. Soc. 1998, 120, 9090-9091.
16. Gallo, E. A.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 9774-9788.
17. Takeda, Y.; Masuda, T.; Matsumoto, T.; Takeshi, Y.; Shingu, T.; Floss, H. G. J. Nat. Prod. 1998, 61, 978-981.
18. Bruun, T. Phytochemistry 1976, 15, 1261-1263.
19. Müller, H.-M.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1993, 32, 477-502.
20. Plattner, D. A.; Brunner, A.; Dobler, M.; Müller, H.-M.; Petter, W.; Zbinden, P.; Seebach, D. Helv. Chim. Acta 1993, 76, 2005-2033.
21. Lengweiler, U. D.; Fritz, M. G.; Seebach, D. Helv. Chim. Acta 1996, 79, 670-701, and references therein.
22. Doi, Y. Microbial Polyesters; VCH: Weinheim, 1990.
23. Polymers of Biological and Biomedical Significance; Shalaby, S. W., Ikada, Y., Langer, R., Williams, J., Eds.; ACS Symposium Series 540; American Chemical Society: Washington, DC, 1994.
24. For a recent example, see: Byung, H. L. Tetrahedron Lett. 1997, 38, 757-760.
25. For a recent example, see: Miyashita, M.; Nakamori, T.; Akamatsu, M.; Murai, T.; Miyagawa, H.; Ueno, T. Pept. Chem. 1996, 34, 137-140.
26. Davies, J. S.; Howe, J.; Jayatilake, J.; Riley, T. Lett. Pept. Sci. 1997, 441-445.
27. For a brief account of these results, see: Kuisle, O.; Quiñoá, E.; Riguera, R. Tetrahedron Lett. 1999, 40, 1203-1206.
28. Neises, B.; Steglich, W. Angew. Chem., Int. Ed. Engl. 1978, 17, 522-524.
29. Latypov, S. K.; Seco, J. M.; Quiñoá, E.; Riguera, R. J. Am. Chem. Soc. 1998, 120, 877-882.
30. Carpino, L. A.; El-Faham, A.; Minor, C. A.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203, and references therein.
31. Han, Y.; Albericio, F.; Barany, G. J. Org. Chem. 1997, 62, 4307-4312.
32. Greene, T. W. Protective Groups in Organic Synthesis; Wiley: New York, 1981.
33. R = 5.89 min). Deprotection was complete when the ratio of these two areas was constant.
34. Pomonis, J. G.; Severson, R. F.; Freeman, P. J. J. Chromatogr. 1969, 40, 78-84.
35. Mitsunobu, O. Synthesis 1981, 1-80.
36. Sieber, P.; Iselin, B. Helv. Chim. Acta 1968, 51, 622-632.
37. Wang, S. S. J. Org. Chem. 1975, 40, 1235-1239.
38. For synthesis of valinomycin analogues in solution, see: Dory, Y. L.; Mellor, J. M.; McAleer, J. F. Tetrahedron 1996, 52, 1343-1360, 1361-1378, and 1379-1388.
39. 1H NMR spectrum of this solid was compared to that obtained from the Bpoc protection and showed the same signals. This means that Bpoc deprotection of the resin-bound didepsipeptide Bpoc-D-Val-L-Lac had not gone to completion and was accomplished in the subsequent THP cleavage with p-TsOH/MeOH.
40. Losse, G.; Klengel, H. Tetrahedron 1971, 27, 1423-1434, and references therein.
41. Jou, G.; González, I.; Albericio, F.; Lloyd-Williams, P.; Giralt, E. J. Org. Chem. 1997, 62, 354-366.
42. Perrin, D.; Armaregeo, W. L. F. Purification of Laboratory Chemicals; Pergamon Press: Oxford, 1988.
43. Kaiser, E.; Colescott, R. L.; Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595-598.