TBTU

peptide coupling reagent CAS# 125700-67-6

TBTU

2D Structure

Catalog No. BCC2823----Order now to get a substantial discount!

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3D structure

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TBTU

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Chemical Properties of TBTU

Cas No. 125700-67-6 SDF Download SDF
PubChem ID 2733207 Appearance Powder
Formula C11H16BF4N5O M.Wt 321.1
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in water or 1% acetic acid
Chemical Name [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium;tetrafluoroborate
SMILES [B-](F)(F)(F)F.CN(C)C(=[N+](C)C)ON1C2=CC=CC=C2N=N1
Standard InChIKey JKEKMBGUVUKMQB-UHFFFAOYSA-N
Standard InChI InChI=1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

TBTU Dilution Calculator

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TBTU Molarity Calculator

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Preparing Stock Solutions of TBTU

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.1143 mL 15.5715 mL 31.1429 mL 62.2859 mL 77.8574 mL
5 mM 0.6229 mL 3.1143 mL 6.2286 mL 12.4572 mL 15.5715 mL
10 mM 0.3114 mL 1.5571 mL 3.1143 mL 6.2286 mL 7.7857 mL
50 mM 0.0623 mL 0.3114 mL 0.6229 mL 1.2457 mL 1.5571 mL
100 mM 0.0311 mL 0.1557 mL 0.3114 mL 0.6229 mL 0.7786 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Organizitions Citing Our Products recently

 
 
 

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Background on TBTU

IC50: Not available.

The utilization of new peptide coupling reagents in organic synthesis has greatly flourished the development of peptide synthesis. TBTU, 2-(1H-Benzotriazol-1-yl)-1,1,3,3-tetramethyluronoium hexafluorphosphate, serves as a typical peptide coupling reagent which has a relatively lower racemization. In normal condition, coupling reactions mediated by TETU take only six minutes to complete when HOBt is added. Moreover, racemization in this reaction could be reduced to insignificant levels. Due to these features, TBTU is regarded as one of the key reagents of choice in both manufactory and lab. [1]

In vitro: It was reported that during synthesis of the macrocyclic peptide cyclotheonamide B, TBTU played an important role in coupling steps. Studies showed that TBTU had been successfully used in several coupling reactions, for instance, this reagent was suitable for couplings involving proline nitrogen, and therefore served as a crucial reagent for the macrolactamization. Although TBTU normally proceeded with little racemization, to suppress the racemization completely, HOBt was also required. Thus, in a typical reaction system, TBTU was added into 0.5 mM solution of CH2Cl2, followed by addition of HOBt and pyridine. Finally, cyclopentapeptide was obtained with a yield of 61%. [1]

In vivo: So far, no in vivo data has been reported.

Clinical trial: So far, no clinical trial has been conducted.

Reference:
[1]Bastiaans HM, van der Baan JL and Ottenheijm HC.  Flexible and convergent total synthesis of cyclotheonamide B. J. Org. Chem. 1997; 62: 3880-9.

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References on TBTU

Occupational rhinitis and bronchial asthma due to TBTU and HBTU sensitization.[Pubmed:12968399]

J Investig Allergol Clin Immunol. 2003;13(2):133-4.

Exposure to an increasing amount of products in the work environment is leading to new cases of occupational asthma among workers. We report the case of a worker at a pharmaceutical plant who developed occupational rhinitis and bronchial asthma due to HBTU: 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate and TBTU: 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate sensitization, two chemical products widely used in peptide synthesis and coupling. Skin tests (prick test) with HBTU and TBTU solutions in PBS were positive at a concentration of 1 mg/ml. Skin tests with the same solutions in 10 atopic controls yielded a negative result. Nasal challenge tests with these products were positive with HBTU at a concentration of 0.01 mg/ml and TBTU at a concentration of 1 mg/ml. In both cases PNIF (peak nasal inspiratory flow) decreased by more than 60% and severe sneezing and rhinorrhea were induced. Nasal challenge tests performed on 10 atopic controls with TBTU and HBTU at a concentration of 1 mg/ml were negative. We conclude that the patient presents occupational rhinitis and bronchial asthma due to TBTU and HBTU; the operational mechanism is probably immunological IgE-mediated given the positive prick tests and nasal challenge with these products.

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