2-Chlorotrityl chloride resin

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 beigeAppearance of substance (visual): beadsLoading (determined from the substitution of the Fmoc-Ala-Leu loaded resin): 1.00 - 1.80 mmol/gSwelling Volume (in CH₂Cl₂): 2.0 - 5.0 ml/gTotal swelling volume acc. Houben Weyl (in CH2Cl2): ≥ 4.2 ml/gThe polymer matrix is copoly (styrene-1 % DVB) 100 - 200 mesh.
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany