| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Not applicable (chemical probe/analytical reagent). Norbiotinamine serves as a biotin replacement tool for studying avidin-biotin interactions and peptide chemistry. It can be coupled to the carboxyl group of an amino acid to form a reverse peptide with an inverted amide bond. This unique property allows researchers to synthesize inverse peptides (retro-peptides) where the amide bond direction is reversed, providing insights into peptide backbone conformation, stability, and recognition by biological targets.
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| 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].
Not applicable (analytical reagent, not a pharmacological agent). Norbiotinamine is coupled with the NHS ester of N-Boc-glutamic acid gamma-benzyl ester to yield a norbiotinylamide derivative, which is structurally similar to biocytin but with a shorter aliphatic chain and an inverted amide bond. This unique biotin replacement is used to study peptide backbone orientation without interference from the natural biotin-streptavidin binding mechanism. |
| ln Vivo |
Not applicable (chemical probe, not intended for therapeutic use in animals). The compound is designed for in vitro biochemical and bioconjugation applications only. As a chemical tool for peptide synthesis and modification, Norbiotinamine is not administered to animals for efficacy studies. Its utility is in the chemical synthesis of modified peptides and the investigation of protein-ligand interactions where the orientation of the amide bond is under investigation.
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| Enzyme Assay |
Not applicable (no enzyme/receptor binding; used in chemical synthesis). For peptide conjugation, a carboxylic acid group on an amino acid (protected as an NHS ester) is reacted with Norbiotinamine (1:1.2 molar ratio) in dry DMF or DMSO containing a base catalyst (e.g., triethylamine, 1-2 equivalents). The reaction is stirred at room temperature for 4-12 hours. The resulting norbiotinyl-amide derivative is purified by preparative HPLC and characterized by mass spectrometry and NMR.
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| Cell Assay |
Not applicable (no cellular assays; used in peptide synthesis and bioconjugation). Norbiotinamine itself is not added to cells. However, peptides modified with Norbiotinamine can be used in cellular assays to study protein-peptide interactions. For example, a biotinylated fumagillin probe synthesized using Norbiotinamine has been used to investigate cell permeability in endothelial and cancer cells. The probe allows detection via avidin-based fluorescence after cellular uptake.
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| Animal Protocol |
Not applicable (chemical probe not used in animal efficacy studies). Norbiotinamine is not administered as a test article in animal models. Its primary applications are in peptide synthesis and in vitro biochemical assays where biotin-streptavidin systems are employed. For pharmacokinetic studies of peptide conjugates containing Norbiotinamine, standard protocols for peptide quantification by LC-MS/MS are used, but the compound itself is not the subject of ADME studies.
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| ADME/Pharmacokinetics |
Not applicable (chemical intermediate, not a systemic drug). Norbiotinamine has a molecular weight of 215.32 g/mol and is stable at 4degC protected from light. The compound is designed for use in solid-phase peptide synthesis or solution-phase conjugation, where its primary amine couples to carboxylic acid groups. The resulting peptide-Norbiotinamine conjugates can be purified by standard chromatographic methods. No systemic absorption data are available or applicable.
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| Toxicity/Toxicokinetics |
Toxicity data are not available for Norbiotinamine as it is a research chemical not intended for therapeutic use. Standard laboratory safety precautions should be observed during handling: avoid inhalation, skin contact, and eye exposure. The compound should be stored at 4degC, protected from light. Based on its structural similarity to biotin, which is generally recognized as safe (GRAS), acute toxicity is expected to be low, but formal LD50 studies have not been conducted.
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| References |
[1]. 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. |
| Additional Infomation |
Norbiotinamine is an alternative to biotin for specialized peptide chemistry applications. Traditional biotin conjugation requires reaction with an amino group (e.g., biocytin). In contrast, Norbiotinamine can be coupled to a carboxyl group, generating reverse peptides with inverted amide bonds. This unique feature is valuable for studying the effects of peptide backbone directionality on biological recognition, stability, and function. The compound is for research use only.
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| Molecular Formula |
C9H17N3OS
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|---|---|
| Molecular Weight |
215.31578040123
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| Exact Mass |
215.109
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| CAS # |
173401-47-3
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| PubChem CID |
58635189
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| Appearance |
White to off-white solid at room temperature
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| LogP |
-0.1
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
14
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| Complexity |
224
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| Defined Atom Stereocenter Count |
3
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| SMILES |
C1[C@H]2[C@@H]([C@@H](S1)CCCCN)NC(=O)N2
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| InChi Key |
KRWAZHNVQMITHZ-FXQIFTODSA-N
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| 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
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| Chemical Name |
(3aS,4S,6aR)-4-(4-aminobutyl)-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-2-one
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| Synonyms |
Norbiotinamine; 173401-47-3; (3AS,4S,6aR)-4-(4-aminobutyl)tetrahydro-1H-thieno[3,4-d]imidazol-2(3H)-one; CHEMBL2063400; CHEMBL2079118;
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| HS Tariff Code |
2934.99.9001
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| 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)
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| Solubility (In Vitro) |
H2O : ~200 mg/mL (~928.9 mM)
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|---|---|
| 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.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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