8.55079

DHP HM resin (100-200 mesh)

Novabiochem^®

• Synonym(s): 3,4-Dihydro-2H-pyran-2-yl-methoxymethyl polystyrene (100-200 mesh), Ellman′s dihydropyran resin
• NACRES: NA.22
• UNSPSC Code: 12162002

Properties

• Quality Segment: 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

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.

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

Other Notes

Replaces: 01-64-0192

Legal Information

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

Safety Information

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