2-Chlorotrityl Chloride Resin |
| Catalog No.GA10388 |
2-Chlorotrityl Chloride Resin (2-CTC resin) is a versatile, acid-labile resin used in the chemical synthesis of peptides using a Fmoc-amino acid/carboxyl-linked protocol for the solid phase immobilization of carboxylic acids, alcohols, phenols, and amines, imidazoles, and hydroxylamines.
Products are for research use only. Not for human use. We do not sell to patients.
Sample solution is provided at 25 µL, 10mM.
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2-Chlorotrityl Chloride Resin (2-CTC resin) is a versatile, acid-labile resin used in the chemical synthesis of peptides using a Fmoc-amino acid/carboxyl-linked protocol for the solid phase immobilization of carboxylic acids, alcohols, phenols, and amines, imidazoles, and hydroxylamines[1]. The conditions of solid phase immobilization release (resin cleavage) are achieved using 1-50% TFA in DCM containing 5% TIS, carboxylic acids can also be cleaved from this support with AcOH/TFE/DCM,0.5% TFA in DCM, or HFIP in DCM[2] [3].
2-Chlorotrityl Chloride Resin act as a temporary and reusable protecting group in facile synthesis of Fmoc-N-Me-AA-OH (150mg, see citation for protocol and condition)[4], synthesis of cathepsin-B cleavable linkers (see citation for protocol and condition)[5], and synthesis of linear and cyclic disulfide heptapeptides of longicalycinin A (see citation for protocol and condition)[6].
References:
[1] Hoekstra, W J. “The 2-chlorotrityl resin: a worthy addition to the medicinal chemist's toolbox.” *Current medicinal chemistry* vol. 8,6 (2001): 715-9. doi:10.2174/0929867013373192
[2] Al Musaimi, Othman et al. “Greener Cleavage of Protected Peptide Fragments from Sieber Amide Resin.” *ChemistryOpen* vol. 11,12 (2022): e202200236. doi:10.1002/open.202200236
[3] Bollhagen, Ralf, et al. "A new reagent for the cleavage of fully protected peptides synthesised on 2-Chlorotrityl Chloride Resin." *Journal of the Chemical Society, Chemical Communications* 22 (1994): 2559-2560.
[4] Román, Tanya et al. “Protocol for Facile Synthesis of Fmoc-N-Me-AA-OH Using 2-CTC Resin as Temporary and Reusable Protecting Group.” *Methods and protocols* vol. 6,6 110. 13 Nov. 2023, doi:10.3390/mps6060110
[5] Pryyma, Alla et al. “Rapid, High-Yielding Solid-Phase Synthesis of Cathepsin-B Cleavable Linkers for Targeted Cancer Therapeutics.” *Bioconjugate chemistry* vol. 31,12 (2020): 2685-2690. doi:10.1021/acs.bioconjchem.0c00563
[6]HoushdarTehrani, Mohammad Hassan et al. “Synthesis of Linear and Cyclic Disulfide Heptapeptides of Longicalycinin A and Evaluation of Toxicity on Cancerous Cells HepG2 and HT-29.” *Iranian journal of pharmaceutical research : IJPR* vol. 17,3 (2018): 956-963. doi:10.1089/sur.2020.189
Prptocal for protected linear disulfide heptapeptide of Longicalycinin A[1]:
1.Attach Fmoc-Cys (Trt)-OH (1170mg, 2mmol) to the 2-CTC resin with DIPEA (1mL) in anhydrous DCM: DMF (30mL, 1:1) at room temperature for 2h.
2.After filtration, cap the remaining trityl chloride groups by a solution of DCM / MeOH / DIPEA (17:2:1; 20mL) for 30min.
3.Filter and wash products with DCM (1 × 10mL), DMF (2 × 20mL).
4.Treat the resin-bound Fmoc-amino acid with Piperazine 10% in DMF (100mL) for 30min.
5.Wash the resin with DMF (4 × 20mL)
6.Add solution of Fmoc-Gly-OH (600mg, 2.01mmol), HATU (650mg, 1.7mmol), and DIPEA (0.5mL) in 10mL DCM to the resin-bound free amine and shaken for 2 h at room temperature.
7.After completion of coupling, wash the resin with DMF (2 × 10mL).
8.Treat the resin with Piperazine 10% in DMF (100mL) for 30min.
9.Wash the resin again with DMF (4 × 20mL).
10.Add other protected amino acids, i.e., Fmoc-Phe-OH, Fmoc-Pro-OH, Fmoc-Tyr (tBu)-OH, Fmoc-Phe-OH and Fmoc-Cys (Trt) - OH to the resin-peptide, sequentially, with the same procedure mentioned as above.
11.Cleave the protected pentapeptide from the resin by treatment of TFA 1% in DCM.
12.Filter and neutralize the product with pyridine 4% in CH3OH.
13.Remove the solvent under reduced pressure and the residue was precipitated in water.
14.Filter and dry the precipitate.
During the synthesis, for detecting the presence or absence of free primary amino groups on the resin-peptide, chloranil test was used.
*This protocol only provides a guideline, and should be modified according to your specific needs
References:
1]HoushdarTehrani, Mohammad Hassan et al. “Synthesis of Linear and Cyclic Disulfide Heptapeptides of Longicalycinin A and Evaluation of Toxicity on Cancerous Cells HepG2 and HT-29.” Iranian journal of pharmaceutical research : IJPR vol. 17,3 (2018): 956-963.
| Cas No. | SDF | ||
| Formula | M.Wt | ||
| Solubility | Storage | Store at -20°C | |
| General tips | Please select the appropriate solvent to prepare the stock solution according to the
solubility of the product in different solvents; once the solution is prepared, please store it in
separate packages to avoid product failure caused by repeated freezing and thawing.Storage method
and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored
at -20°C, please use it within 1 month. To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time. |
||
| Shipping Condition | Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request. | ||
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
g
μL
Step 2: Enter the in vivo formulation (This is only the calculator, not formulation. Please contact us first if there is no in vivo formulation at the solubility Section.)
Calculation results:
Working concentration: mg/ml;
Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )
Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
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