Norbiotinamine

• CAT Number: I016847
• CAS Number: 173401-47-3
• Molecular Formula: C9H17N3OS
• Molecular Weight: 215.32
• Purity: ≥95%
• Synonyms: (3aS,4S,6aR)-4-(4-aminobutyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
• InChI: InChI=1S/C9H17N3OS/c10-4-2-1-3-7-8-6(5-14-7)11-9(13)12-8/h6-8H,1-5,10H2,(H2,11,12,13)/t6-,7-,8-/m0/s1
• InChIKey: KRWAZHNVQMITHZ-FXQIFTODSA-N
• SMILES: C1C2C(C(S1)CCCCN)NC(=O)N2

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].
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].

Reference

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