T511552

PTAD-Azide

Aldrich^CPR

• Synonym(s): 4-(4-(2-Azidoethoxy)phenyl)-1,2,4-triazolidine-3,5-dione, N_3-Ph-Ur for e-Y-CLICK
• Empirical Formula (Hill Notation): C₁₀H₁₀N₆O₃
• CAS Number: 1313211-52-7
• Molecular Weight: 262.22
• MDL number: MFCD25976544
• UNSPSC Code: 12352125
• PubChem Substance ID: 329826813

Properties

• SMILES string: O=C(NNC1=O)N1C2=CC=C(OCCN=[N+]=[N-])C=C2
• InChI: 1S/C10H10N6O3/c11-15-12-5-6-19-8-3-1-7(2-4-8)16-9(17)13-14-10(16)18/h1-4H,5-6H2,(H,13,17)(H,14,18)
• InChI key: MHGMHPVYCVQIET-UHFFFAOYSA-N

Description

Application

PTAD-Azide is a selective bioconjugation reagent for the modification of tyrosine residues with an azide. Subsequent modification can then be afforded via the azide/alkyne click chemistry reaction with an alkyne or cyclooctyne containing compound or biomolecule. This reagent has been shown to selectively introduce poly(ethylene glycol) or PEG chains onto proteins with surface exposed tyrosine residues. PTAD-Azide has also been used in the formation of antibody-drug conjugates. This reagent is compatible with different buffer systems such as PBS, Tris and mixed PBS/Tris buffer (preferred). The linkage with tyrosine has been shown to be stable to pH and temperature extremes as well as blood plasma.
   
Note: PTAD-Azide must be first activated by stirring in a 1:0.98 molar ratio with 1,3-dibromo-5,5-dimethylhydantoin (product # 157902). Activation is evident upon solution color change from colorless to deep red and the activated reagent should be used immediately.
 
 
General Procedure for Protein Modification with PTAD.
 
Part 1: PTAD activation

• Mix together 1:0.98 molar equivalents of unactivated PTAD to 1,3-dibromo-5,5-dimethylhydantoin (product # 157902) in organic solvent (preferred solvents are DMF or acetonitrile; avoid using DMSO)
• Color change is observed from colorless/pale yellow to deep red (approximately 5 min of mixing).
• After the solution turns red, store the now activated reagent on ice and use for protein modification within 30 min.

 
Part 2: Protein modification

• Add protein solution in mixed phosphate/Tris buffer or Tris buffer (pH should be 6 - 9) to the eppendorf tube (or other vial) containing the activated PTAD reagent prepared above and mix gently at room temperature for up to 30 min. Preferably use 10-fold molar excess of reagent relative to protein. Use protein at a minimum concentration of 1 mg/ml (higher concentrations are preferred for enhanced labeling).
• Remove excess unreacted PTAD by gel filtration.

Packaging

Each AldrichCPR product will be packaged in one consolidated unit unless you specify multiple units at the time of order.

Other Notes

Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.

NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable