Solid phase synthesis of peptide hydroxamic acids

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1511-1514

  Chen, Jack J ^a   Spatola, Arno F ^a  

^a UNIVERSITY OF LOUISVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; PEPTIDE;

ARTICLE; DRUG SYNTHESIS; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0031550887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00143-3     Document Type: Article

References (23)

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2. b) Gowravaram, M. R.; Tomczuk, B. E.; Johnson, J. S.; Delecki, D.; Cook, E. R.; Ghose, A. K.; Mathiowetz, A. M.; Spurlino, J. C.; Rubin, B.; Smith, D. L.; Pulvino, T.; Wahl, R. C. J. Med. Chem. 1995, 38, 2570-2581;
3. c) Feehan, C.; Darlak, K.; Kahn, J.; Walcheck, B.; Spatola, A. F.; Kishimoto, T. K. J. Biol. Chem. 1996, 271, 7019-7024;
4. d) Mohler, K. M.; Sleath, P. R.; Fitzner, J. N.; Cerretti, D. P.; Alderson, M.; Kerwar, S. S.; Torrance, D. S.; Otten-Evans, C.; Greenstreet, T.; Weerewarna, K.; Kronheim, S. R.; Petersen, M.; Gerhart, M.; Kozlosky, C. J.; March, C. J.; Black, R. A. Nature 1994, 370, 218-220;
5. e) Spatola, A. F.; Gray, R. D.; Darlak, K., U.S Patent 5, 387, 610;
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7. g) Wong, G. B.; Kappel, M. J.; Raymond, K. N.; Matzanke, B.; Winkelmann, G. J. Am. Chem. Soc. 1983, 105, 810-815.
8. 2. a) For a comprehensive review on the synthesis of hydroxamic acids, see: Sandler, S. R.; Karo, W. In Organic Functional Group Preparations; Blomquist, A. T.; Wasserman, H. Eds.; Academic Press, Inc., New York, 1972, Vol 3, 406-432;
9. b) For a novel solution phase method, see: Pirrung, M. C.; Chau, J. H.-L. J. Org. Chem. 1995, 60, 8084-8085.
10. 3. a) Nikam, S. S.; Kornberg, B. E.; Johnson, D. R.; Doherty, A. M. Tetrahedron Lett. 1995, 36, 197-200;
11. b) Isowa, Y.; Takashima, T.; Ohmori, M.; Kurita, H.; Sato, M.; Mori, K. Bull. Chem. Soc. Jpn. 1972, 45, 1467-1471;
12. c) Masaki, M.; Ohtake, J.; Sugiyama, M.; Ohta, M. Bull. Chem. Soc. Jpn. 1965, 38, 1802.
13. 4. a) Munegumi, T.; Hoshino, S.; Naito, K.; Izawa, T.; Pept. Chem. 1994, 32, 217-220;
14. b) Kolasa, T.; Chimiak, A. Tetrahedron 1974, 30, 3591-3595.
15. 2a Analytically pure peptide hydroxamic acids were obtained after separating crude product on semi-preparative RP-HPLC.
16. 6. a) Bayer, E.; Henkel, B.; Nicholson, G. In Peptides: Chemistry, Structure and Biology; Kaumaya, P. T. P.; Hodges, R. S. Eds.; Mayflower Sci. Ltd, 1996, pp 132-133;
17. b) Sharma, R. P.; Jones, D. A.; Broadbridge, R. J.; Corina, D. L.; Akhtar, M. In Innovation and Perspectives in Solid Phase Synthesis: Peptides, Proteins and Nucleic Acids; Epton, R. Ed.; Mayflower Worldwide Ltd., Birmingham, England, 1994, pp. 353-356.
18. 2 became well diffused, BOP (0.19 g, 0.42 mmol) was added as a solid. DIEA (0.074 ml, 0.42 mmol) was added at last to effect the coupling reaction. The reaction suspension was stirred overnight. The resin was then washed and dried in vacuo.
19. 8. a) Alsina, J.; Giralt, E.; Albericio, F. Tetrahedron Lett. 1996, 37, 4195-4198;
20. b) Kates, S. A.; Triolo, S. A.; Diekmann, E.; Carpino, L. A.; El-Faham, A.; Ionescu, D.; Albericio, F. In Peptides: Chemistry, Structure and Biology; Kaumaya, P. T. P.; Hodges, R. S. Eds.; Mayflower Sci. Ltd, 1996, 115-116;
21. c) Carpino, L. A.; El-Faham, A.; Minor, C.; Albericio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203.
22. 2OBz1 and DIEA in THF. No observable reaction was detected with Boc-Asp(OBz1)-OH after 72 hr stirring at ambient temperature.
23. 10. While this manuscript was in preparation, Floyd et al. (Tetrahedron Lett. 1996, 37, 8045-8048) described the solid phase synthesis (Fmoc approach) of hydroxamic acids in which this group is directly attached to the support, facilitating the synthesis of C-terminal peptide hydroxamates.