Acyclic and cyclic thioenamino peptides: solution- and solid-phase synthesis

Tetrahedron Letters

Volumn 50, Issue 9, 2009, Pages 1048-1050

  Goren, Lee ^a   Pappo, Doron ^a   Goldberg, Israel ^a   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

Cyclic peptides; Endiamine; FGly; Solid phase synthesis; Thioenamine

Indexed keywords

AMINE; KETONE DERIVATIVE; PEPTIDE DERIVATIVE; PIPERAZINE DERIVATIVE; THIAZEPINE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; HYDROGEN BOND; REACTION ANALYSIS; SOLID PHASE SYNTHESIS; X RAY DIFFRACTION;

EID: 58149515937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.072     Document Type: Article

References (32)

1. Berer N., Rudi A., Goldberg I., Benayahu Y., and Kashman Y. Org. Lett. 6 (2004) 2543-2545
2. Pappo D., Vartanian M., Lang S., and Kashman Y. J. Am. Chem. Soc. 127 (2005) 7682-7683
3. Pappo D., and Kashman Y. Org. Lett. 8 (2006) 1177-1179
4. Marshall G.R. Tetrahedron 49 (1993) 3547-3558
5. Chruszez M., Laidler P., Monkiewicz M., Ortlund E., Lebioda L., and Lewinski K. J. Inorg. Biochem. 96 (2003) 386-392
6. It is suggested that cyclic endiamino peptides are obtained in Nature by the condensation of FGly (formylglycine) with the amine of an amino acid. FGly, which is known in Nature only as a hydrate in active sites of enzymes, is unstable in solution, and has therefore to be protected as, for example, enol-tosylate (FGly-OTs) 1. The latter moiety was shown to function as the free aldehyde.
7. Nakazawa T., Suzuki T., and Ishii M. Tetrahedron Lett. 38 (1997) 8951-8954
8. Sulfonyl chloride resin, Sigma-Aldrich, # 498211.
9. +)).
10. +)) data.
11. Smith J.A., and Pease L.G. CRC Crit. Rev. Biochem. 8 (1980) 315-399
12. Examples of peptides forming γ-turns:. Levian-Teitlbaum D., Kolodny N., Chorev M., Selinger Z., and Gilon C. Biopolymers 28 (1989) 51-64
13. Raghothama S., Ramakrishnan C., Balasubramanian D., and Balaram P. Biopolymers 28 (1989) 573-588
14. Milon A., Miyazawa T., and Higashijima T. Biochemistry 29 (1990) 65-75
15. Walse B., Kihlberg J., and Drakenberg T. Eur. J. Biochem. 252 (1998) 428-440
16. For γ-turn mimetics, see:. Schmidt B., Lindman S., Tong W., Lindeberg G., Gogoll A., Lai Z., Thörnwall M., Synnergren B., Nilsson A., Welch C.J., Sohtell M., Westerlund C., Nyberg F., Karlén A., and Hallberg A. J. Med. Chem. 40 (1997) 903-919
17. Brickmann K., Yuan Z., Sethson I., Somfai P., and Kihlberg J. Chem. Eur. J. 5 (1999) 2241-2253
18. Jiménez A.I., Cativiela C., and Marraud M. Tetrahedron Lett. 41 (2000) 5353-5356
19. +)) data.
20. +)) data. Inter alia, the HMBC experiment showed a correlation between H-2 and C-7 in the ring. A characteristic vinylic thioenamino proton resonance at δ 7.12 (s) ppm, and the corresponding carbon at δ 121.1 ppm were present.
21. 2 = 0.103) for all unique data. Crystal data for the structural analysis have been deposited with the Cambridge Crystallographic Data Centre, CCDC 709744. The supplementary crystallographic data for this Letter can be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1233 336033; e-mail: deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk/).
22. +)) data. The characteristic vinylic thioenamino proton resonance at δ 7.20 (s) ppm, and the corresponding carbon at δ 120.9 ppm were present.
23. [S-(R*,S*)]-6-[(2-Mercapto-1-oxo-3-phenylpropyl)amino]-4,5,6,7-tetrahydro-2-methyl-5-oxo-1,4-thiazepine-3-carboxylic acid has been reported for its therapeutic potential as an ACP/NEP dual inhibitor. Crescenza A., Botta M., Corelli F., Santini A., and Tafi A. J. Org. Chem. 64 (1999) 3019-3025
24. +)). The characteristic vinylic thioenamino proton resonance at δ 7.39 (s) ppm, and carbon resonance at δ 144.5 ppm were present.
25. Well R.M.V., Marinelli L., Altona C., Erkelens K., Siegal G., Raaij M.V., Liamas- Saiz A.L., Kessler H., Novellino E., Lavecchia A., Van Boom J.H., and Overhand M. J. Am. Chem. Soc. 125 (2003) 10822-10829
26. Imperiali B., Fisher S.L., Moats R.A., and Prins T.J. J. Am. Chem. Soc. 114 (1992) 3182-3188
27. Jeannotte G., and Lubell W.D. J. Am. Chem. Soc. 126 (2004) 14334-14335
28. Xiao J., Weisblum B., and Wipf P. J. Am. Chem. Soc. 127 (2005) 5742-5743
29. Martins M.B., and Carvalho I. Tetrahedron 63 (2007) 9923-9932
30. Fischer P.M. J. Peptide Sci. 9 (2003) 9-35
31. +)) data. The characteristic vinylic thioenamino proton resonance at δ 6.64 (s) ppm, and carbon resonance at δ 122.9 ppm were present.
32. Disclosure of reverse-turn regions of biologically active peptides and proteins; Moon, S. H. U.S. Pat. Appl. Publ. 826, 972, 2007; Chem. Abst. 146, 274, 627.