N-Fmoc-aminooxy-2-chlorotrityl polystyrene resin: A facile solid-phase methodology for the synthesis of hydroxamic acids

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3311-3314

  Mellor, Sarah L ^a   McGuire, Carolann ^a   Chan, Weng C ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID; PEPTIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; TECHNIQUE;

EID: 0030893753     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00594-7     Document Type: Article

References (18)

1. A preliminary account was presented at the 24th European Peptide Symposium, Edinburgh, UK, 8-13 September 1996, P120.
2. Abbreviations: Fmoc, 9-fluorenylmethoxycarbonyl; HOAt, l-hydroxy-7-azabenzotriazole;HATU, O-(7-azabenzotriazol-1-yl)-l,l,3,3-tetramethyluronium hexafluorophosphate; DIPEA, N,N-diisopropylethylamine; HOBt, 1-hydroxybenzotriazole; TBTU, O-(benzotriazol-l-yl)-l,l,3,3-tetramethyluronium tetrafluoroborate; TFA, trifluoroacetic acid. Amino acid derivatives used for peptide synthesis were Fmoc-Trp(Boc)-OH and Fmoc-Arg(Pmc)-OH.
3. Burke, T. R.; Fesen, M. R.; Mazumder, A.; Wang, J.; Carothers, A. M.; Grunberger, D.; Driscoll, J.; Kohn, K.; Pommier, Y. J. Med. Chem. 1995, 38, 4171-4178; Tamaki, K.; Ogita, T.; Tanzawa, K.; Sugimura, Y. Tetrahedron Lett. 1993, 28, 683-686; Bihovsky, R.; Levison, B. L.; Loewi, R. C.; Erhardt, P.W.; Polokoff, M. A. J. Med. Chem. 1995, 38, 2119-2129.
4. Burke, T. R.; Fesen, M. R.; Mazumder, A.; Wang, J.; Carothers, A. M.; Grunberger, D.; Driscoll, J.; Kohn, K.; Pommier, Y. J. Med. Chem. 1995, 38, 4171-4178; Tamaki, K.; Ogita, T.; Tanzawa, K.; Sugimura, Y. Tetrahedron Lett. 1993, 28, 683-686; Bihovsky, R.; Levison, B. L.; Loewi, R. C.; Erhardt, P.W.; Polokoff, M. A. J. Med. Chem. 1995, 38, 2119-2129.
5. Burke, T. R.; Fesen, M. R.; Mazumder, A.; Wang, J.; Carothers, A. M.; Grunberger, D.; Driscoll, J.; Kohn, K.; Pommier, Y. J. Med. Chem. 1995, 38, 4171-4178; Tamaki, K.; Ogita, T.; Tanzawa, K.; Sugimura, Y. Tetrahedron Lett. 1993, 28, 683-686; Bihovsky, R.; Levison, B. L.; Loewi, R. C.; Erhardt, P.W.; Polokoff, M. A. J. Med. Chem. 1995, 38, 2119-2129.
6. Onishi, H. R.; Pelak, B. A.; Gerkens, L. S.; Silver, L. L.; Kahan, F. M.; Chen, M-H.; Patchett, A. A.; Galloway, S. M.; Hyland, S. A.; Anderson, M. S.; Raetz, C. R. H. Science 1996, 274, 980-982.
7. Floyd, C. D.; Lewis, C. N.; Patel, S. R.; Whittaker, M. Tetrahedron Lett. 1996, 37, 8045-8048; Richter, L. S.; Desai, M. C. Tetrahedron Lett. 1997, 38, 321-322.
8. Floyd, C. D.; Lewis, C. N.; Patel, S. R.; Whittaker, M. Tetrahedron Lett. 1996, 37, 8045-8048; Richter, L. S.; Desai, M. C. Tetrahedron Lett. 1997, 38, 321-322.
9. -1 , which was used to calculate % efficiency.
10. Barlos, K.; Chatzi, O.; Gatos, D.; Stavropoulos, G. Int. J. Peptide Protein Res. 1991, 37, 513-520.
11. -l). However, following Fmoc-deprotection, it is worth noting that we were unable to acylate the resin-bound secondary amine to any significant level; a raft of activation chemistry was evaluated. We concluded that this observation is the result of severe steric constraint.
12. Carpino, L.A. J. Am. Chem. Soc. 1993, 115, 4397-4398; Carpino, L.A.; El-Faham, A.; Minor, C.A.; Albericio, F. J. Chem. Soc., Chem. Commun., 1994, 201-203.
13. Carpino, L.A. J. Am. Chem. Soc. 1993, 115, 4397-4398; Carpino, L.A.; El-Faham, A.; Minor, C.A.; Albericio, F. J. Chem. Soc., Chem. Commun., 1994, 201-203.
14. The dried resin 2 was allowed to swell overnight in dichloromethane prior to use. Furthermore, acylation of the Fmoc-deprotected 2 was carried out at r.t for 24 h.
15. + 249.3, found 249.2.
16. Bycroft, B.W.; Chan, W.C.; Chhabra; S.R.; Hone, N.D. J. Chem. Soc., Chem. Commun. 1993, 778-779; Bycroft, B.W.; Chan, W.C.; Hone, N.D.; Millington, S.; Nash,I .A. J. Am. Chem. Soc. 1994, 116, 7415-7416; Nash, I.A.; Bycroft, B.W.; Chan, W.C. Tetrahedron Lett. 1996, 37, 2625-2628.
17. Bycroft, B.W.; Chan, W.C.; Chhabra; S.R.; Hone, N.D. J. Chem. Soc., Chem. Commun. 1993, 778-779; Bycroft, B.W.; Chan, W.C.; Hone, N.D.; Millington, S.; Nash,I .A. J. Am. Chem. Soc. 1994, 116, 7415-7416; Nash, I.A.; Bycroft, B.W.; Chan, W.C. Tetrahedron Lett. 1996, 37, 2625-2628.
18. Bycroft, B.W.; Chan, W.C.; Chhabra; S.R.; Hone, N.D. J. Chem. Soc., Chem. Commun. 1993, 778-779; Bycroft, B.W.; Chan, W.C.; Hone, N.D.; Millington, S.; Nash,I .A. J. Am. Chem. Soc. 1994, 116, 7415-7416; Nash, I.A.; Bycroft, B.W.; Chan, W.C. Tetrahedron Lett. 1996, 37, 2625-2628.