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 beige
Appearance of substance (visual): beads
Loading (determined from the substitution of the Fmoc-Gly-ol loaded resin): 0.70 - 1.20 mmol/g
Swelling Volume (in CH₂Cl₂): lot specific result
The polymer matrix is copoly (styrene-1% DVB), 100 - 200 mesh
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
Quality Level: 200. product line: Novabiochem®. . form: beads. reaction suitability: reaction type: Fmoc solid-phase peptide synthesis, reactivity: alcohol reactive. manufacturer/tradename: Novabiochem®. . application(s): peptide synthesis. storage temp.: 2-8°C. Storage Class Code: 11 - Combustible Solids. WGK: WGK 1. Flash Point(F): Not applicable. Flash Point(C): Not applicable.- UPC:
- 51282812
- Condition:
- New
- Availability:
- 3-5 Days
- Weight:
- 1.00 Ounces
- HazmatClass:
- No
- MPN:
- 8550790001
