DHP HM resin (100-200 mesh)

Description

• General description: A highly versatile support for the solid phase immobilization of primary, secondary alcohols [1,2,3,4,5,6,7,8,9,10,11], phenols [12], purines [13], and indoles [14]. Derivatization is effected by treating the support in DCM with an excess of alcohol in the presence of a catalytic amount of pyridinium p-toluenesulfonate. A similar DHP-based support has also been used for the immobilization of tetrazoles [15].Release of the product alcohol from the support has been carried out by treating with 95% TFA/5% water[1] and TFA/DCM/EtOH [2,12]. However, the use of TFA can lead, in some cases, to trifluoroacetate formation. Methods which eliminate this potential side reaction include PPTS/BuOH/DCE [3], TosOH in DCM [16] and TosOH in DCE/BuOH [17]. Associated Protocols and Technical Articles Protocols for Loading of Peptide Synthesis Resins Literature references[1] L. A. Thompson & J. A. Ellman (1994) Tetrahedron Lett., 35, 9333. [2] O. B. Wallace (1997) Tetrahedron Lett., 38, 4939. [3] G. Liu & J. A. Ellman (1995) J. Org. Chem., 60, 7712. [4] E. K. Kick & J. A. Ellman (1995) J. Med. Chem., 38, 1427. [5] J. S. Koh & J. A. Ellman (1996) J. Org. Chem., 61, 4494. [6] J. Cossy, et al. (2000) Synlett, 3, 409. [7] M. Ramaseshan, et al. (2000) J. Comb. Chem., 2, 615. [8] M. Ramaseshan, et al. (2000) Tetrahedron Lett., 41, 4743. [9] A. Bianco, et al. (2000) J. Org. Chem., 65, 2179. [10] M. Steger, et al. (2001) Bioorg. Med. Chem. Lett., 11, 2537. [11] A. Dahlgren, et al. (2003) Bioorg. Med.Chem. Lett., 11, 827. [12] W. H. Pearson & R. B. Clark (1997) Tetrahedron Lett., 38, 7669. [13] D. A. Nugiel, et al. (1997) J. Org. Chem., 62, 201. [14] A. L. Smith, et al. (1998) Tetrahedron Lett., 39, 8317. [15] S.-E. Yoo, et al. (1997) Tetrahedron Lett., 38, 1203. [16] J. Beythien (Merck Biociences AG), personal communication. [17] M. R. Tremblay, et al. (1999) Bioorg. Med . Chem. Lett., 9, 2827.
• Linkage: Replaces: 01-64-0192
• Analysis Note: Color (visual): slight yellow to beigeAppearance of substance (visual): beadsLoading (determined from the substitution of the Fmoc-Gly-ol loaded resin): 0.70 - 1.20 mmol/gSwelling Volume (in CH₂Cl₂): lot specific resultThe polymer matrix is copoly (styrene-1% DVB), 100 - 200 mesh
• Legal Information: Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany