| Autor: |
Valerio, R. M., Bray, A. M., Maeji, N. J., Morgan, P. O., Perich, J. W. |
| Zdroj: |
Letters in Peptide Science; August 1995, Vol. 2 Issue: 1 p33-40, 8p |
| Abstrakt: |
The synthesis of two model Tyr(P)-containing peptides using Fmoc-Tyr(PO3tBu2)-OH, Fmoc-Tyr(PO3Bzl2)-OH and Fmoc-Tyr(PO3H2)-OH established that the t-butylphosphate-protected derivative was the preferred derivative for use in Fmoc solid-phase peptide synthesis, since it afforded phosphopeptides in high purity and with the lowest amount of Tyr-peptide contamination. In addition, this study confirmed that commercially available Fmoc-Tyr(PO3H2)-OH is also suitable for use in Fmoc solid-phase synthesis but gives less pure phosphopeptides, along with the generation of 1–4% of the tyrosine-containing peptide for the model sequences studied. In view of the good performance of Fmoc-Tyr(PO3tBu2)-OH, a ‘large-scale’ three-step synthetic procedure was developed which involved phenacyl protection of the carboxyl group, ‘phosphite-triester’ phosphorylation of the tyrosyl hydroxyl using di-t-butyl N,N-diethylphosphoramidite, and final removal of the phenacyl group by zinc reduction in acetic acid. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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