Norbiotinamine

Norbiotinamine is an alternative to biotin. Norbiotinamine can be coupled with a carboxylic group of amino acids to give inverse peptides, having the amide linkage oriented in the opposite direction[1].

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

In order to couple biotin to amino acids, reaction has to be with an amino group. An example is biocytin (biotin lysine). However, Norbiotinamine could be coupled with a carboxylic group of amino acids to give inverse peptides, having the amide linkage oriented in the opposite direction. As an example, Norbiotinamine is coupled with the NHS ester of N-Boc-glutamic acid γ-benzyl ester. The resulting norbiotinylamide of γglutamic acid (VII), obtained after deprotection, is similar to biocytin, but it has a shorter aliphatic chain and an inverted amide bond[1].

[1]. Szalecki W.Synthesis of Norbiotinamine and its derivatives. Bioconjug Chem. 1996 Mar-Apr;7(2):271-3.

[2]. Zhou GC, et al. Design, synthesis and evaluation of a cellular stable and detectable biotinylated fumagillin probe and investigation of cell permeability of fumagillin and its analogs to endothelial and cancer cells.Eur J Med Chem. 2013;70:631-9.