Norbiotinamine is an alternative to biotin. Norbiotinamine can be coupled to the carboxyl group of an amino acid (AA) to give a reverse peptide with an inverted amide bond.

Physicochemical Properties

Molecular Formula	C9H17N3OS
Molecular Weight	215.31578040123
Exact Mass	215.109
CAS #	173401-47-3
PubChem CID	58635189
Appearance	Typically exists as solid at room temperature
LogP	-0.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Heavy Atom Count	14
Complexity	224
Defined Atom Stereocenter Count	3
SMILES	C1[C@H]2[C@@H]([C@@H](S1)CCCCN)NC(=O)N2
InChi Key	KRWAZHNVQMITHZ-FXQIFTODSA-N
InChi Code	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
Chemical Name	(3aS,4S,6aR)-4-(4-aminobutyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro

To attach biotin to an amino acid, a reaction with the amino group must occur. One example is biocytin (biotin lysine). However, norbiotinamine can be linked to an amino acid's carboxyl group to form a reverse peptide with the amide bond in the opposite orientation. For instance, norbiotinamine is linked to the NHS ester of N-Boc-glutamic acid γ-benzyl ester. The norbiotinamide of gamma glutamic acid (VII) formed following deprotection resembles biocytin, but it has a shorter aliphatic chain and a reverse amide bond [1].

References

[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.

Solubility Data

Solubility (In Vitro)	H2O : ~200 mg/mL (~928.85 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (464.43 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	4.6443 mL	23.2213 mL	46.4425 mL
	5 mM	0.9289 mL	4.6443 mL	9.2885 mL
	10 mM	0.4644 mL	2.3221 mL	4.6443 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.