On the use of N-dicyclopropylmethyl aspartyl-glycine synthone for backbone amide protection.

Autor: Röder, René, Henklein, Petra, Weißhoff, Hardy, Mügge, Clemens, Pätzel, Michael, Schubert, Ulrich, Carpino, Louis A., Henklein, Peter
Zdroj: Journal of Peptide Science; Jan2010, Vol. 16 Issue 1, p65-70, 6p
Abstrakt: To prevent aspartimide formation and related side products in Asp-Xaa, particularly Asp-Gly-containing peptides, usually the 2-hydroxy-4-methoxybenzyl (Hmb) backbone amide protection is applied for peptide synthesis according to the Fmoc-protocols. In the present study, the usefulness of the recently proposed acid-labile dicyclopropylmethyl (Dcpm) protectant was analyzed. Despite the significant steric hindrance of this bulky group, N-terminal H-(Dcpm)Gly-peptides are quantitatively acylated by potent acylating agents, and alternatively the dipeptide Fmoc-Asp(OtBu)-(Dcpm)Gly-OH derivative can be used as a building block. In contrast to the Hmb group, Dcpm is inert toward acylations, but is readily removed in the acid deprotection and resin-cleavage step. Copyright © 2009 European Peptide Society and John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index