Triethyl 2-acetoxypropane-1,2,3-tricarboxylate

Name: Triethyl 2-acetoxypropane-1,2,3-tricarboxylate
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CAS No. 77-89-4
Cat. No. CS-W009904
Purity≥98%
MDL No.MFCD00049378

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Triethyl 2-acetoxypropane-1,2,3-tricarboxylate|CS-W009904

Structure of 77-89-4

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General Information

CAS No. 77-89-4
Cat. No. CS-W009904
Purity ≥98%
MDL No. MFCD00049378
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₄H₂₂O₈
Molecular Weight 318.32
Synonym(s) Triethyl O-acetylcitrate
SMILES O=C(CC(C(OCC)=O)(OC(C)=O)CC(OCC)=O)OCC

Description

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 activationMix 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 modificationAdd 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.

Synthesis

Route1
- 77-93-0
- 108-24-7
- ~92%
- In-stock
  
  77-89-4
References
- Liu, Zhihui; Ma, Qiaoqiao; Liu, Yuxiu; Wang, Qingmin Organic Letters, 2014 , vol. 16, # 1 p. 236 - 239
Route2
- 77-93-0
- 75-36-5
- ~%
- In-stock
  
  77-89-4
References
- Justus Liebigs Annalen der Chemie, , vol. 129, p. 187

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 105.2
LogP 0.7578
H_Acceptors 8
H_Donors 0
Rotatable_Bonds 9

Other Classifications

Building Blocks Functional Group Boc

Building Blocks Functional Group Ester

Material Science Polymer Materials Polymer Additives

Material Science Polymer/Macromolecule Reagents Polymer Additives Plasticizers

Key Words

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Triethyl 2-acetoxypropane-1,2,3-tricarboxylate

CAS No. 77-89-4

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