Synthesis of a cyclic-thioether peptide which binds anti-cardiolipin antibodies

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6107-6110

  Jones, David S ^a   Gamino, Christina A ^a   Randow, Martina E ^a   Victoria, Edward J ^a   Yu, Lin ^a   Coutts, Stephen M ^a  

^a La Jolla Pharmaceutical Company   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARDIOLIPIN ANTIBODY; CYCLOPEPTIDE; PROLINE DERIVATIVE; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0032552122     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01292-1     Document Type: Article

References (23)

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2. 2. For a review of phage libraries, see Smith, G. N. and Petrenko, V. A.. Chem. Rev. 1997, 97, 391-410.
3. 3. Sem, D. S.; Baker, B. L.; Victoria, E. J.; Jones, D. S.; Marquis, D.; Yu, L.; Parks, J.; and Coutts, S. M. (manucript in preparation).
4. 4. Thaisrivongs, S.; Pals, D. T.; Lawson, J. A.; Turner, S. R.; and Harris, D. W. J. Med. Chem. 1987, 30, 536-541.
5. 5. Jones, D. S.; Hachmann, J. P.; Osgood, S. A.; Hayag, M. S.; Barstad, P. A.; Iverson, G. M.; and Coutts, S. M. Bioconjugate Chemistry 1994, 5, 390-399.
6. 6. Jones, D. S.; Barstad, P. A.; Field, M. J.; Hachmann, J. P.; Hayag, M. S.; Hill, K. W.; Iverson, G. M.; Livingston, D. A.; Palanki, M. S.; Tibbetts, A. R.; Yu, L.; Coutts, S. M.. J. Med. Chem. 1995, 38, 2138-2144.
7. 7. Mihara, H.; Yamabe, S.; Niidome, T. and Aoyagi, H. Tetrahedron Letters 1995, 36, 4837-4840.
8. 8. McMurray, J. S. and Lewis, C. A.. Tetrahedron Letters 1993, 34, 8059-8062.
9. 9. Katz, B. A.; Johnson, C. R. and Cass, R. T. J. Am. Chem. Soc. 1995, 117, 8541-8547.
10. 10. Mayer, J. P.; Heil, J. R.; Zhang, J. and Munson, M. C. Tetrahedron Letters 1995, 36, 7387-7390.
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12. 12. Barton, D. H. R.; Herve, Y.; Potier, P. and Thierry, J. Tetrahedron 1988, 44, 5479-5486.
13. 13. Seebach, D.; Boes, M.; Naef, R. and Schweizer, W. B. J. Am. Chem. Soc. 1983, 105, 5390-5398.
14. 2-glycoprotein I), NHS (N-hydroxysuccinimide), DCC (1,3-dicyclohexylcarbodiimide), HOBT (1-hydroxybenzotriazole), DIC (1,3-diisopropykarbodumide), DBU (l,8-diazabicyclo[5.4.0]undec-7-ene), DPPA (diphenylphosphoryl azide).
15. +: 423.193. Found: 423.1904.
16. 7: C, 54.96; H, 5.89; N, 10.68. Found: C, 55.18; H, 6.16; N, 10.70.
17. 2: C, 61.37; H, 6.09; N, 6.51. Found: C, 61.47; H, 6.03; N, 6.51.
18. 7S: C, 62.08; H, 6.89; N, 7.01. Found: C, 62.23; H, 7.12; N, 7.39.
19. 9S: C, 58.52; H, 6.21; N, 10.03. Found: C, 58.38; H, 6.17; N, 10.20.
20. 2 and a few drops of DMF was prepared and cooled to 0°C and treated with DIC for 20 minutes at 0°C. The mixture was concentrated and dissolved in DMF, and the resulting solution was added to preswelled HMPB-MBHA resin (Novabiochem) followed by DMAP dissolved in DMF (1 eq of per eq of resin substitution). After 1 hour the resin was washed (2 X DMF, 2 X MeOH, 2 X DMF, 2 X MeOH) and dried. The substitution was determined to be 0.540 mmol/g.
21. +.
22. +.
23. 50 is the concentration of peptide that inhibited ACA binding by 50%.