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Phosphine-biotin

(Synonyms: Click Tag Phosphine-biotin) 目录号 : GC44634

A probe for azido-labeled proteins

Phosphine-biotin Chemical Structure

Cas No.:608514-42-7

规格 价格 库存 购买数量
500μg
¥1,918.00
现货
1mg
¥3,649.00
现货
5mg
¥15,350.00
现货

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Sample solution is provided at 25 µL, 10mM.

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产品描述

Labeling reactive centers of various types in cells with specific site-directed probes is a common method to explore both function and biochemical modification of proteins. The popular click chemistry method of protein labeling employs use of a reaction between an azido group and an alkyne on complimentary pairs of a specific reactive probe and a labeling agent (i.e. a tag) such as biotin or a fluorophore. The Staudinger ligation is an alternative to the click chemistry reaction in which a phosphine-labeled molecule reacts with an azido group on the opposing molecule of interest. Phosphine biotin is a labeling reagent that selectively reacts with azido groups on modified proteins through the Staudinger ligation reaction. Modified proteins can be detected using common avidin-based biochemical techniques in whole cells or by blotting experiments following SDS-PAGE. For example, phosphine-biotin has been used successfully in conjunction with DAz-1 or DAz-2 to label and detect sulfenic acid sites in proteins.

Reference:
[1]. Seo, Y.H., and Carroll, K.S. Facile synthesis and biological evaluation of a cell-permeable probe to detect redox-regulated proteins. Bioorganic & Medicinal Chemistry Letters 19, 356-359 (2009).
[2]. Reddie, K.G., Seo, Y.H., Muse, W.B., III, et al. A chemical approach for detecting sulfenic acid-modified proteins in living cells. Molecular BioSystems 4, 521-531 (2008).

Chemical Properties

Cas No. 608514-42-7 SDF
别名 Click Tag Phosphine-biotin
化学名 2-(diphenylphosphino)-4-[21-[(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1,17-dioxo-6,9,12-trioxa-2,16-diazaheneicos-1-yl]-benzoic acid, methyl ester
Canonical SMILES O=C1N[C@]2([H])[C@]([C@H](CCCCC(NCCCOCCOCCOCCCNC(C3=CC=C(C(OC)=O)C(P(C4=CC=CC=C4)C5=CC=CC=C5)=C3)=O)=O)SC2)([H])N1
分子式 C41H53N4O8PS 分子量 792.9
溶解度 DMSO: 2 mg/ml 储存条件 Store at -20°C
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1 mM 1.2612 mL 6.306 mL 12.6119 mL
5 mM 0.2522 mL 1.2612 mL 2.5224 mL
10 mM 0.1261 mL 0.6306 mL 1.2612 mL
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Research Update

A new, robust, and nonradioactive approach for exploring N-myristoylation

J Lipid Res 2012 Nov;53(11):2459-68.PMID:22829651DOI:PMC3466015

Myristoyl-CoA (CoA):protein N-myristoyltransferase (NMT) catalyzes protein modification through covalent attachment of a C14 fatty acid (myristic acid) to the N-terminal glycine of proteins, thus promoting protein-protein and protein-membrane interactions. NMT is essential for the viability of numerous human pathogens and is also up-regulated in several tumors. Here we describe a new, nonradioactive, ELISA-based method for measuring NMT activity. After the NMT-catalyzed reaction between a FLAG-tagged peptide and azido-dodecanoyl-CoA (analog of myristoyl-CoA), the resulting azido-dodecanoyl-peptide-FLAG was coupled to Phosphine-biotin by Staudinger ligation, captured by plate-bound anti-FLAG antibodies and detected by streptavidin-peroxidase. The assay was validated with negative controls (including inhibitors), corroborated by HPLC analysis, and demonstrated to function with fresh or frozen tissues. Recombinant murine NMT1 and NMT2 were characterized using this new method. This versatile assay is applicable for exploring recombinant NMTs with regard to their activity, substrate specificity, and possible inhibitors as well as for measuring NMT-activity in tissues.