2 chlorotrityl chloride resin

Overview

 

2 chlorotrityl chloride resin (off-white to light yellow beads) is a very versatile resin so it is widely used for SPPS immobilization of various groups including alcohols, carboxylic acid, amines, phenols, imidazoles, thiols and hydroxylamines. AcOH/TFE/DCM, 0.5% TFA or HFIP in DCM, or 1-5% TFA in DCM containing 5% TIS are used to achieve cleavage. Racemization can be effectively avoided by introducing this resin due to its high steric hindrance. Some research has been done recently to investigate the properties of 2 chlorotrityl chloride resin to explain its role in Solid Phase Peptide Synthesis. 2 chlorotrityl chloride resin reacting with Fmoc amino acids was found following the same path of the reaction between Triphenylmethyl chloride (TrCl)  and nucleophiles.  It is proved that 2 chlorotrityl chloride reacts with nucleophiles via extremely fast heterolytic cleavage and the chloride trityl cation formed is very stable. Experiments are performed over several selected solvents to examine the property of 2 chlorotrityl chloride during esterification with Fmoc protected amino acids. DCE and DCM result in quantitative esterificaiton, however THF, DMF and DMAC give low esterification yield. 3.2 fold molar excess of DIEA was used in those experiments and it is found that the esterification yield stays unchanged as the amount of DIEA is decreased to 1:1. The esterification of Fmoc protected amino acids is very fast. 95% esterification yield can be achieved in a very short time (less than 10 minutes) with various chloride substitution.

2 chlorotrityl chloride resin, (or 2-Cl-Trt chloride resin),  is an acid labile, suitable for the synthesis of protected  or free peptide fragments (normally under extremely mild acid conditions). In order to be used in such application,  the ester bond against acid cannot either be too stable during cleavage or too weak during coupling, washing and N-Deprotection steps. Researchers looked at a property that ensures quantitative splitting of the peptide without damaging the protecting side chain groups. The properties of several candidate resins were selected and investigated, and revealed that 2 chlorotrityl chloride resin is the best choice in balancing the stability according to a research published in the 1990s.

 

We are offering

Applied Polytech offers 100-200 and 200-400 mesh, 1% DVB, typical substitution levels range from 0.4-1.6mmol/g of 2 chlorotrityl chloride resin in bulk and lab scale quantity at attractive prices. To provide better customer care, we also offer ready-to-use preloaded resins with Amino Acid Attached to 2-Cl-Trt Resins. Here is a full list of preloaded resins with Amino Acid Attached to 2-Cl-Trt Resins:

H-Ala-2Cl-Trt Resin, H-Arg(Pbf)-2Cl-Trt Resin, H-Asn-2Cl-Trt Resin, H-Asn(Trt)-2Cl-Trt Resin, H-Asp(OtBu)-2Cl-Trt Resin, H-Cys(Acm)-2Cl-Trt Resin, H-Cys(Trt)-2Cl-Trt Resin, H-Gln-2Cl-Trt Resin, H-Gln(Trt)-2Cl-Trt Resin, H-Glu(OtBu)-2Cl-Trt Resin, H-Gly-2Cl-Trt Resin, H-His(Trt)-2Cl-Trt Resin, H-Ile-2Cl-Trt Resin, H-Leu-2Cl-Trt Resin, H-Lys(Boc)-2Cl-Trt Resin, H-Met-2Cl-Trt Resin, H-Phe-2Cl-Trt Resin, H-Pro-2Cl-Trt Resin, H-Ser(tBu)-2Cl-Trt Resin, H-Ser(Trt)-2Cl-Trt Resin, H-Thr(tBu)-2Cl-Trt Resin, H-Thr(Trt)-2Cl-Trt Resin, H-Trp-2Cl-Trt Resin, H-Trp(Boc)-2Cl-Trt Resin, H-Tyr(tBu)-2Cl-Trt Resin, H-Tyr(Trt)-2Cl-Trt Resin, H-Val-2Cl-Trt Resin.

Due to the moisture sensitive characteristic, 2 chlorotrityl chloride resin should be stored in a tightly closed container. Blanketing with nitrogen in the headspace of the container is recommended to achieve longer shelf life. 

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