Synthesis of the Simple Peptide Model Ac-Abu(PO3H2)-NHMe

Autor: Valerio, RM, Perich, JW, Alewood, PF, Tong, G, Johns, RB
Zdroj: Australian Journal of Chemistry; 1992, Vol. 45 Issue: 4 p777-784, 8p
Abstrakt: The simple model substrate AC-L-Abu(PO3H2)- NHMe was prepared by the use of the protected 4( diethylphosphono ) butanoic acid derivative Boc -Abu(PO3Et2)-OH in the Boc mode of solution phase peptide synthesis. The protected peptide model Ac-Abu(P03Et2)- NHMe was prepared by initial reaction of the isobutoxycarbonyl mixed anhydride of Boc-Abu(PO3Et2)-OH with N-methylamine followed by cleavage of the Boc group from Boc -Abu(PO3Et2)- NHMe with 4 M HCl/dioxan and N- acetylation of H-Abu(PO3Et2)-NHMe.HCl with the isobutoxycarbonyl mixed anhydride of acetic acid. Cleavage of the phosphonate ethyl groups was effected with 33% hydrogen bromidelacetic acid or 10% bromotrimethylsilane/acetonitrile to give AC-L-Abu(PO3H2)-NHMe in near-quantitative yield.
Databáze: Supplemental Index