Chloro-(2'-chloro)trityl Polystyrene

Product information

A very acid sensitive resin suitable for the synthesis of protected peptide fragments by the Fmoc strategy. In particular suitable for the preparation of C-terminal prolyl and cysteinyl peptides. Cleavage from this resin is achieved by using 1-95% TFA in DCM (containing 8% triisopropylsilane), AcOH/CF3OH/DCM, 0.5% TFA or hexafluoroisopropanol. Recently, this resin has been used in cyclization reactions under Heck reaction conditions, the solid phase synthesis of ß-peptides via the Arndt-Eistert homologation of Fmoc-protected amino acid diazoketones and in Mannich reactions of alkynes, secondary amines and aldehydes in the presence of a copper (I) salt leading to the corresponding aminomethyl alkynyl adducts.This resin can also be used in Fmoc peptide synthesis. Carboxylic acids can be released under very mild acidic conditions by treatment with AcOH/TFE/DCM or HFIP in DCM. Completely protected peptides are generated under these conditions.
This resin is less sensitive towards acids compared to chlorotrityl resins.
Coupling of the first amino acid is not carried out by activation, thus enantiomerization does not occur.


L 37 Chloro-(2’-chloro)trityl Polystyrene Resins

  1. Barlos, K.; Gatos, D.; Kallitsis, J.; Papaphotiu, G.; Sotiriu, P.; Wenqing, Y.; Schäfer, W. Darstellung geschützter Peptidfragmente unter Einsatz substituierter Triphenylmethyl-Harze. Tetrahedron Lett. 1989, 30 (30), 3943-3946. doi: 10.1016/s0040-4039(00)99290-6.
  2. Barlos, K.; Gatos, D.; Kapolos, S.; Papaphotiu, G.; Schäfer, W.; Wenqing, Y. Veresterung von partiell geschützten Peptidfragmenten mit Harzen. Einsatz von 2-Chlortritylchlorid zur Synthese von Leu15 -gastrin I. Tetrahedron Lett. 1989, 30 (30), 3947-3950. doi: 10.1016/s0040-4039(00)99291-8.
  3. Barlos, K.; Gatos, D.; Schäfer, W. Synthesis of Prothymosinα(ProTα)—a Protein Consisting of 109 Amino Acid Residues. Angew. Chem. Int. Ed. Engl. 1991, 30 (5), 590-593. doi: 10.1002/anie.199105901.
  4. Barlos, K., Chatzi, O., Gatos, D., Stavropoulos, G. 2-Chlorotrityl chloride resin, Studies on anchoring of Fmoc-amino acids and peptide cleavage. Int. J. Peptide Protein Res. 1991, 37 (6), 513-520. doi: 10.1111/j.1399-3011.1991.tb00769.x
  5. Barlos, K.; Gatos, D.; Kutsogianni, S.; Papaphotiou, G.; Poulos, C.; Tsegenidis, T. Solid Phase Synthesis of Partially Protected and Free Peptides Containing Disulphide Bonds by Simultaneous Cysteine Oxidation-Release from 2-Chlorotrityl Resin. Int. J. Pept. Protein Res. 1991, 38 (6), 562-568. doi: 10.1111/j.1399-3011.1991.tb01540.x.
  6. Barlos, K.; Gatos, D.; Kapolos, S.; Poulos, C.; Schäfer, W.; Yao, W. Q. Application of 2-Chlorotrityl Resin in Solid Phase Synthesis of (Leu15)-Gastrin I and Unsulfated Cholecystokinin Octapeptide. Selective O-Deprotection of Tyrosine. Int. J. Pept. Protein Res. 1991, 38 (6), 555-561. doi: 10.1111/j.1399-3011.1991.tb01539.x.
  7. Barlos, K.; Gatos, D.; Papaphotiou, G.; Schäfer, W. Synthese von Calcitonin-Derivaten durch Fragmentkondensation in Lösung und am 2-Chlortrityl-Harz. Liebigs Ann. Chem. 1993, 1993 (3), 215-220. doi: 10.1002/jlac.199319930139.
  8. Egner, B. J.; Cardno, M.; Bradley, M. Linkers for Combinatorial Chemistry and Reaction Analysis Using Solid Phase in Situ Mass Spectrometry. J. Chem. Soc. Chem. Commun. 1995, No. 21, 2163-2164. doi: 10.1039/c39950002163.
  9. Leznoff, C. C. The Use of Insoluble Polymer Supports in General Organic Synthesis. Acc. Chem. Res. 1978, 11 (9), 327-333. doi: 10.1021/ar50129a002.
  10. Nash, I. A.; Bycroft, B. W.; Chan, W. C. Dde - A Selective Primary Amine Protecting Group: A Facile Solid Phase Synthetic Approach to Polyamine Conjugates. Tetrahedron Lett. 1996, 37 (15), 2625-2628. doi: 10.1016/0040-4039(96)00344-9.
  11. Hoekstra, W. J.; Greco, M. N.; Yabut, S. C.; Hulshizer, B. L.; Maryanoff, B. E. Solid-Phase Synthesis via N-Terminal Attachment to the 2-Chlorotrityl Resin. Tetrahedron Lett. 1997, 38 (15), 2629-2632. doi: 10.1016/s0040-4039(97)00447-4.
  12. Akaji, K.; Kiso, Y. Macrocyclization on Solid Support Using Heck Reaction. Tetrahedron Lett. 1997, 38 (29), 5185-5188. doi: 10.1016/s0040-4039(97)01123-4.
  13. Marti, R. E.; Bleicher, K. H.; Bair, K. W. Solid Phase Synthesis of β-Peptides via Arndt-Eistert Homologation of Fmoc-Protected Amino Acid Diazoketones. Tetrahedron Lett. 1997, 38 (35), 6145-6148. doi: 10.1016/s0040-4039(97)01420-2.
  14. Bollhagen, R.; Schmiedberger, M.; Barlos, K.; Grell, E. A New Reagent for the Cleavage of Fully Protected Peptides Synthesised on 2-Chlorotrityl Chloride Resin. J. Chem. Soc. Chem. Commun. 1994, No. 22, 2559. doi: 10.1039/c39940002559.
  15. Fujiwara, Y.; Akaji, K.; Y Kiso, Y. Racemization-Free Synthesis of C-Terminal Cysteine-Peptide Using 2-Chlorotrityl Resin. Chem. Pharm. Bull. 1994, 42 (3), 724-726. doi: 10.1248/cpb.42.724.
  16. McNally, J. J.; Youngman, M. A.; Dax, S. L. Mannich Reactions of Resin-Bound Substrates: 2. A Versatile Three-Component Solid-Phase Organic Synthesis Methodology. Tetrahedron Lett. 1998, 39 (9), 967-970. doi: 10.1016/s0040-4039(97)10716-x.
  17. Shankar, B. B.; Yang, D. Y.; Girton, S.; Ganguly, A. K. One Pot Solid Phase Synthesis of Isoxazolines. Tetrahedron Lett. 1998, 39 (17), 2447-2448. doi: 10.1016/s0040-4039(98)00237-8.