Unexpected Formation of Tetramethylguanidines by Reaction of Dimethylformamide with Fmoc-Protected Aminoamides

Abstract

Reactions of primary amines with Fmoc-protected amino acids or Fmoc deprotection of the resulting products in N,N-di­methylformamide gave tetramethylguanidines in variable yields as unexpected by-products.

guanidine - peptide synthesis - Fmoc protection - Fmoc deprotection - dimethylformamide

References

<A NAME="RD02511ST-1">1</A> Subasinghe KR. Jackson WR. Young JF. Papanastasiou M. Jarrott B. Aust. J. Chem.  2004,  57:  427 

<A NAME="RD02511ST-2">2</A> Meglitskii VA. Kvasha NM. Khim. Volokna  1971,  3:  70 

<A NAME="RD02511ST-3">3</A> Fields G. Methods for Removal of the Fmoc Group, In Peptide Synthesis Protocols   Pennington MW. Dunn BM. Humana Press; New Jersey: 1994.  p.17-27