| Cross Linker (DVB): | 1% |
| Particle Size (mesh): | 100-200 |
| Loading (mmol/g): | 0.4-1.0 |
| 2-Chlorotrity chloride resin is slightly less acid-labile than Trityl Resin and thus more widely used in solid phase peptide synthesis [1-6]. This resin has been also widely used in solid phase organic synthesis by immobilizing carboxylic acid [7,8], alcohols [9-10], phenols [11,12], amines [13-16], imidazoles [17], hydroxylamines [18,19], and thiols [20] on it. Cleavage is achieved using AcOH/TFE/DCM [1-6], 0.5% TFA or HFIP in DCM, or 1-5% TFA in DCM containing 5% TIS. Trityl linkers have certain advantages in comparison to the alkoxybenzyl alcohol (eg. Wang resin), especially in the area of peptide chemistry. First, the problem of racemization during the loading of the first amino acid (using DIPEA) is avoided with trityl linkers. Second, due to steric factors, no diketopiperazine formation is observed [2,4,21]. References [1] K. Barlos, et al., Tetrahedron Lett., 1989, 30, 3943 [2] K. Barlos, et al., Tetrahedron Lett., 1989, 30, 3947 [3] K. Barlos, et al., Angew. Chem. Int. Ed. Engl., 1991, 30, 590 [4] K. Barlos, et al., Int. J. Pept. Protein Res., 1991, 37, 513 [5] K. Barlos, et al., Int. J. Pept. Protein Res., 1991, 38, 562 [6] J. Bódi, et. al., Tetrahedron Lett. 1997, 38, 3293 [7] J. B. Laursen, et al., Bioorg. Med. Chem. Lett. 2002, 12, 171 [8] B. Drouillat, et al., Bioorg. Med. Chem. Lett. 1997, 7, 2247 [9] H. Wenschuh, et al., J. Org. Chem., 1995, 60, 405 [10] M. A. F. Biabani, et al., Tetrahedron Lett. 2001, 42, 7119 [11] Z. Zhu & B. Mckittrick, Tetrahedron Lett., 1998, 39, 7479 [12] U. Heinelt, et al., Bioorg. Med. Chem. Lett., 2001, 11, 227 [13] M. Cardno, et al., J. Chem. Soc. Chem. Commun., 1995, 2163 [14] I. A. Nash, et al. Tetrahedron Lett., 1996, 37, 2625 [15] W. J. Hoekstra, et al., Tetrahedron Lett., 1997, 38, 2629 [16] J. Perumattan, et al., Mol.Div., 1998, 3, 121 [17] J. M. Henlin, et al., J. Pept. Res., 2001, 57, 419 [18] S. L. Mellor, et al., Tetrahedron Lett., 1997, 38, 3311. [19] M. M. Meloni & M. Taddei, Org.Lett., 2001, 3, 337. [20] S. Mourtas, et al., Tetrahedron Lett., 2003, 44, 179 [21] K. Barlos, et al., Ann. Chem., 1993, 215 |
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