8.55017

2-Chlorotrityl chloride resin

100-200 mesh, 1% DVB, Novabiochem^®

• Synonym(s): 2-Chlorotrityl chloride resin
• UNSPSC Code: 12352101
• NACRES: NA.22

Properties

• product name: 2-Chlorotrityl chloride resin (100-200 mesh), 1% DVB, Novabiochem^®
• Quality Level: 200
• product line: Novabiochem^®
• form: beads
• reaction suitability: reaction type: Fmoc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• Storage temp.: 2-30°C

Description

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).

Linkage

Replaces: 01-64-0114

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.

Legal Information

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: Not applicable
• flash_point_c: Not applicable