PeptideDB

11-Azidoundecanoic acid 118162-45-1

11-Azidoundecanoic acid 118162-45-1

CAS No.: 118162-45-1

11-Azidoundecanoic acid is a chemical reagent bearing an azide (N3) moiety and is a hydrophobic biocoupling agent. 11-Az
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11-Azidoundecanoic acid is a chemical reagent bearing an azide (N3) moiety and is a hydrophobic biocoupling agent. 11-Azidoundecanoic acid, as a hydrophobic bioconjugator, can be further modified at the azide position using Staudinger ligation or Click-chemistry. 11-Azidoundecanoic acid is a labeled substrate for lipoic acid ligase (LpIA).

Physicochemical Properties


Molecular Formula C11H21N3O2
Molecular Weight 227.30
Exact Mass 227.163
CAS # 118162-45-1
PubChem CID 454094
Appearance White to off-white solid powder
LogP 3.344
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor Count 4
Rotatable Bond Count 11
Heavy Atom Count 16
Complexity 225
Defined Atom Stereocenter Count 0
SMILES

O([H])C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N=[N+]=[N-])=O

InChi Key LXAVFOAOGZWQKT-UHFFFAOYSA-N
InChi Code

InChI=1S/C11H21N3O2/c12-14-13-10-8-6-4-2-1-3-5-7-9-11(15)16/h1-10H2,(H,15,16)
Chemical Name

11-azidoundecanoic acid
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 On a designed LplA acceptor peptide (LAP), the microbial lipoic acid ligase LplA has the ability to selectively bind an alkyl azide. Subsequently, the alkyl azide preferentially transforms into cyclooctyne conjugates for a range of probes[1]. Using tiny fluorophores provided by means of a brief peptide tag, the LplA approach could enable widespread access to biochemical and imaging studies of cell surface proteins[1].
References [1]. Fernández-Suárez M, et al. Redirecting lipoic acid ligase for cell surface protein labeling with small-molecule probes. Nat Biotechnol. 2007 Dec;25(12):1483-7.
[2]. Heal WP, et al. N-Myristoyl transferase-mediated protein labelling in vivo. Org Biomol Chem. 2008 Jul 7;6(13):2308-15.

Solubility Data


Solubility (In Vitro) DMSO : 100 mg/mL (439.95 mM)
Solubility (In Vivo) Solubility in Formulation 1: ≥ 2.5 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

Solubility in Formulation 3: ≥ 2.5 mg/mL (11.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.3995 mL 21.9974 mL 43.9947 mL
5 mM 0.8799 mL 4.3995 mL 8.7989 mL
10 mM 0.4399 mL 2.1997 mL 4.3995 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.