A TFA-cleavable linkage for solid-phase synthesis of hydroxamic acids

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 321-322

  Richterand, Lutz S ^a,b   Desai, Manoj C ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

^b NOVO NORDISK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID;

ARTICLE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0343471944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02336-2     Document Type: Article

References (13)

1. For examples, see a) Johnson, W.H.; Roberts, N.A.; Borkakoti, N., J. Enzyme Inhibition 1987, 2, 1;
2. b) Wahl, R.C.; Dunlap, R.P.; Morgan, B.A. in Annual Reports in Medicinal Chemistry 25, Bristol, J.A. (ed.), Academic Press, New York 1990, 177;
3. c) Holmes, M.A.; Matthews, B.W., Biochemistry 1981, 20, 6912.
4. a) Thompson, L.A.; Ellman, J.A., Chem. Rev. 1996, 96, 555;
5. b) Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M., J. Med. Chem. 1994, 37, 1233;
6. c) Gordon, E.M.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A., J. Med. Chem. 1994, 37, 1386.
7. Richter, L.S.; Desai, M.C., manuscript in preparation.
8. Rink, H., Tetrahedron Lett. 1987, 28, 3787.
9. Mergler, M.; Tanner, R.; Gosteli, J.; Grogg, P., Tetrahedron Lett. 1988, 29, 4005.
10. Wang, S.S., J. Am. Chem. Soc. 1973, 95, 1328.
11. Fields, G.B.; Noble, R.L., Int. J. Pept. Protein Res. 1990, 35, 161.
12. Zuckermann, R.N.; Kerr, J.M.; Kent, S.B.H.; Moos, W.H., J. Am. Chem. Soc. 1992, 114, 10646.
13. In order to prevent TFA-induced hydrolysis of acid-sensitive hydroxamates to the corresponding carboxylic acids, we recommend to cleave the resin under anhydrous conditions.