8.55068

Hydroxymethyl polystyrene

100-200 mesh, 1% DVB, Novabiochem^®

• Synonym(s): Polystyrene-CH ₂OH (100-200 mesh)
• UNSPSC Code: 13111023
• NACRES: NA.22

Properties

• product name: Hydroxymethyl polystyrene (100-200 mesh), 1% DVB, Novabiochem^®
• Quality Level: 200
• product line: Novabiochem^®
• form: beads
• reaction suitability: reaction type: Boc solid-phase peptide synthesis
• manufacturer/tradename: Novabiochem^®
• application(s): peptide synthesis
• functional group: alcohol
• storage temp.: 2-30°C

Description

General description

This resin is ideal for the solid phase immobilization of carboxylic acids. Less cross-linking is observed than with Merrifield resin during the attachment of diacids ^[1]. Reaction with a suitable phosgene equivalent converts this resin to a support suitable for the immobilization of amines ^[2]. Release of carboxylic acids from this support is normally effected by treatment of the resin with H For TFMSA, or by hydrogenolysis ^[3]. Alcohols can be liberated by reduction with DIBAL ^[4] or LiBH4^[5]. Methyl esters can be produced by transesterification with MeONa ^[6] or Ti(OEt)4/CH3CO2Me ^[7]. Carboxamides are also accessible via Lewis acid catalyzed aminolysis ^[8].

Associated Protocols and Technical Articles
Protocols for Loading of Peptide Synthesis Resins

Literature references

^[1] J. M. Goldwasser, et al. (1978) Can. J. Chem., 56,1562.
^[2] D. J. Burdick, et al. (1993) Tetrahedron Lett., 34,2589.
^[3] J. M. Schlatter, et al. (1977) Tetrahedron Lett., 2851.
^[4] M. J. Kurth, et al. (1994) J. Org. Chem., 59,5862.
^[5] J. M. Stewart & J. D. Young in ′Solid Phase Peptide Synthesis, 2nd Ed.′, Rockford, Illinois, Pierce Chemical Company, 1984, pp. 92.
^[6] R. Frenette, et al. (1994) Tetrahedron Lett., 35,9177.
^[7] L. T. Tietze & A. Steinmetz (1996) Angew. Chem. Int. Ed.Engl., 35, 651.
^[8] D. R. Barn, et al. (1996) TetrahedronLett., 37, 3213.

Linkage

Replaces: 01-64-0110

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined from the substitution of the Fmoc-Leu loaded resin): 0.60 - 1.60 mmol/g
Swelling Volume (in DMF): 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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable