General description
2-Chlorotrityl chloride resin is an extremely versatile, acid-labile resin for the solid phase immobilization of carboxylic acids [¹,²,³,⁴,⁵,⁶, ²⁰], alcohols [⁷,⁸,⁹, ²⁰], phenols [¹⁰,¹¹,¹²,¹³, ²⁰] and amines [¹⁴,¹⁵,¹⁶,¹⁷,¹⁸,¹⁹,²⁰], imidazoles [²⁰] and hydroxylamines[²¹,²²]. Release of these functionalities is generally achieved using 1-50% TFA in DCM containing 5% TIS, although carboxylic acids can also be cleaved from this support with AcOH/TFE/DCM [¹,²,³,⁴,⁵,⁶],0.5% TFA in DCM, or HFIP in DCM [²³].
Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis ResinsLiterature references
[¹] K. Barlos, et al. (1989) Tetrahedron Lett., 30, 3947.
[²]K. Barlos, et al. (1989) Tetrahedron Lett., 30, 3943.
[³] K. Barlos, et al. (1991) Angew. Chem. Int. Ed. Engl., 30, 590.
[⁴]K. Barlos, et al. (1991) Int. J. Peptide Protein Res., 37, 513.
[⁵] K. Barlos, et al. (1991) Int. J. Peptide Protein Res., 38, 562.
[⁶]K. Barlos, et al. (1991) Int. J. Peptide Protein Res., 38, 555.
[⁷] H. Wenschuh, et al. in ′Peptides 1994, Proc. 23rd European Peptide Symposium′, H. Maia (Eds), ESCOM, Leiden, 1995, pp. 287.
[⁸] H. Wenschuh, et al. (1995) J. Org. Chem., 60, 405.
[⁹] B. B. Shankar, et al. (1998) Tetrahedron Lett., 39, 2447.
[¹⁰]Z. Zhu & B. Mckittrick (1998) Tetrahedron Lett., 39, 7479.
[¹¹]U. Heinelt, et al. (2001) Bioorg. Med. Chem. Lett., 11, 227.
[¹²] K. J. Elgie, et al. (2000) Tetrahedron Lett., 41, 2753.
[¹³] S. Batra, et al. (2000) Tetrahedron Lett., 41, 5971.
[¹⁴] M. Cardno, et al. (1995) J. Chem. Soc., Chem. Commun., 2163.
[¹⁵] I. A. Nash, et al. (1996) Tetrahedron Lett., 37, 2625.
[¹⁶]W. J. Hoekstra, et al. (1997) Tetrahedron Lett., 38, 2629.
[¹⁷] J. Perumattan, et al. (1998) Mol. Div., 3, 121.
[¹⁸] J. J. McNally, et al. (1998) Tetrahedron Lett., 39,967.
[¹⁹]M. A. Youngman & S. L. Dax (1997) Tetrahedron Lett., 38, 6347.
[²⁰] A. Bernhardt, et al. (1997) J. Peptide Res., 50, 143.
[²¹] S. L. Mellor, et al. (1997) Tetrahedron Lett., 38, 3311.
[²²] M. M. Meloni & M. Taddei (2001) Org. Lett., 3, 337.
[²³]R. Bollhagen, et al. (1994) J. Chem. Soc ., Chem. Commun., 2559.
Application
Efficient Synthesis of Protein Mimics by Sequential Native Chemical Ligation: This study utilized 2-Chlorotrityl chloride resin (100-200 mesh, 1% DVB) for solid-phase peptide synthesis, highlighting its effective use in complex peptide assembly processes. (Kruijtzer & Liskamp).
Analysis Note
Colour (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined from the substitution of the Fmoc-Ala-Leu loaded resin): 1.00 - 1.80 mmol/g
Swelling Volume (in CH₂Cl₂): 2.0 - 5.0 ml/g
Total swelling volume acc. Houben Weyl (in CH₂Cl₂): ≥ 4.2 ml/g
The polymer matrix is copoly (styrene-1 % DVB) 100 - 200 mesh.
Other Notes
Replaces: 01-64-0114
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
