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8.55068

Sigma-Aldrich

Hydroxymethyl polystyrene

100-200 mesh, 1% DVB, Novabiochem®

Synonym(s):

Polystyrene-CH 2OH (100-200 mesh)

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About This Item

UNSPSC Code:
13111023
NACRES:
NA.22

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

Related Categories

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

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Protocols

Boc Resin Cleavage Protocol

Anhydrous HF is the preferred reagent for peptide cleavage from Boc-based resins, versatile and effective for various peptide synthesis.

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