NHS-LC-Biotin

- Overview
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    Background
    
    NHS-LC-biotin (succinimidyl-6-(biotinamindo)hexanoate), also known as NHS-X-biotin is a derivative of D-biotin, a amine-reactive biotinylation agent, that contains a spacer arm off the valeric acid side chain of D-biotin with an NHS ester group at its end. The NHS ester group at the end of NHS-LC-biotin covalently binds to amine groups in proteins and other molecules forming a stable amide linkage and releasing the NHS group. The 6-aminocaproic acid spacer of NHS-LC-biotin greatly increases the length between a covalently modified molecule and the bicyclic biotin rings leading to a better binding potential for avidin or streptavidin probes. NHS-LC-biotin is insoluble in aqueous environments requiring the dissolution of organic solvents prior to the addition to a buffered reaction.
    Reference
    Bioconjugate Techniques , 2nd ed. By Greg T.Hermanson (Pierce Biotechnology, Thermo Fisher Scientific, Rockford, IL). Academic Press (an imprint of Elsevier): London, Amsterdam, Burlington, San Diego . 2008. ISBN 978-0-12-370501-3.
- Properties
  - Categories
    
    Amine-reactive biotinylation reagent, long chain
    
    Alternative Name
    
    Succinimidyl 6-(biotinamido)hexanoate
    
    CAS Number
    
    72040-63-2
    
    Molecular Formula
    
    C20H30N4O6S
    
    Molecular Weight
    
    454.54
    
    Purity
    
    98.00%
    
    Solubility
    
    ≥22.73 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    C1CC(=O)N(C1=O)OC(=O)CCCCCNC(=O)CCCCC2C3C(CS2)NC(=O)N3
    
    * For Research Use Only
- Reference
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    2. JIUHE ZHU. "The regulation of neuronal excitability by epilepsy-associated gene Nedd4-2." University of Illinois. Urbana-Champaign, 2019
    3. Kamperman T, Koerselman M, et al. "Spatiotemporal material functionalization via competitive supramolecular complexation of avidin and biotin analogs." Nat Commun. 2019 Sep 25;10(1):4347. PMID:31554812
    4. Zhang X, Qiu M, et al. "Autologous Red Blood Cell Delivery of Betamethasone Phosphate Sodium for Long Anti-Inflammation." Pharmaceutics. 2018 Dec 18;10(4). pii: E286. PMID:30567356
    5. Zhu J, Lee KY, et al. "Epilepsy-associated gene Nedd4-2 mediates neuronal activity and seizure susceptibility through AMPA receptors." PLoS Genet. 2017 Feb 17;13(2):e1006634. PMID:28212375