Collect. Czech. Chem. Commun.
2001, 66, 923-932
https://doi.org/10.1135/cccc20010923
Epimerization During Coupling to the Unnatural Amino Acid in Solid Phase Peptide Synthesis
Zhenyu Zhang, Arthur Van Aerschot, Patrick Chaltin, Roger Busson and Piet Herdewijn*
Laboratory of Medicinal Chemistry, Rega Institute for Medical Research, Katholieke Universiteit Leuven, Minderbroedersstraat 10, Leuven, 3000, Belgium
References
1. J. Med. Chem. 1994, 37, 1233.
< M. A., Barrett R. W., Dower W. J., Fodor S. P. A., Gordon E. M.: https://doi.org/10.1021/jm00035a001>
2. Tetrahedron 1993, 49, 11065.
< P., Albericio F., Giralt E.: https://doi.org/10.1016/S0040-4020(01)81800-7>
3. C&EN 1998, 6, 47.
< S.: https://doi.org/10.1021/cen-v076n014.p047>
4. Doyle P. M., Barker E., Harris C. J., Slater M. J.: Pharm. Tech. Eur. 1998, April, 26.
5. Chem. Eur. J. 1998, 4, 425.
< T., Hendrix C., Kerremans L., Rozenski J., Link A., Samyn B., Van Aerschot A., Lescrinier E., Eritja R., Van Beeumen J., Herdewijn P.: https://doi.org/10.1002/(SICI)1521-3765(19980310)4:3<425::AID-CHEM425>3.0.CO;2-W>
6. Int. J. Peptide Protein Res. 1990, 35, 161.
< G. B., Noble R. L.: https://doi.org/10.1111/j.1399-3011.1990.tb00939.x>
7. Tetrahedron Lett. 1998, 39, 8529.
< A. D., Tancredi M., Galoppini C., Rovero P.: https://doi.org/10.1016/S0040-4039(98)01891-7>
8. Org. Lett. 1999, 1, 91.
< H., Jiang X., Ye Y., Fan C., Romoff T., Goodman M.: https://doi.org/10.1021/ol990573k>
9. Tetrahedron 1991, 47, 259.
< E., Coste J., Pantalomi A., Dufour M., Jouin P.: https://doi.org/10.1016/S0040-4020(01)80922-4>
10. Tetrahedron 1999, 55, 6813.
< L. A., El-Faham A.: https://doi.org/10.1016/S0040-4020(99)00344-0>
11. The calculation is based on the percentage of one isomer e.g. D in the total mixture of both isomers (D plus L).
12. Chem. Rev. (Washington, D. C.) 1997, 97, 2243.
< J. M., Chamberlin A. R.: https://doi.org/10.1021/cr950005s>
13. J. Org. Chem. 1994, 59, 695.
< L., El-Faham A.: https://doi.org/10.1021/jo00083a001>