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8.55060

Sigma-Aldrich

Rink Acid resin (100-200 mesh)

Novabiochem®

Synonym(s):

4-(2′,4′-Dimethoxyphenyl-hydroxymethyl)-phenoxy resin

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About This Item

UNSPSC Code:
13111023
NACRES:
NA.22

Quality Level

product line

Novabiochem®

form

beads

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

alcohol

storage temp.

2-30°C

General description

Rink acid resin is a super acid-labile support for the solid phase immobilization of carboxylic acids [1] by Fmoc SPPS. Cleavage can be effected with as little as 10% AcOH in DCM, providing highly acid-sensitive products in high yields and purities. However, care must be taken to prevent product loss during synthetic manipulations [2], owing to the extreme acid sensitivity of this support. Treatment with HCl in THF [3] or Ph2PCl2 [4] has been shown to efficiently convert this resin to the corresponding benzhydryl chloride, to which can be coupled a wide range of functional groups: hydroxylamines [3], alcohols, amines, acids and thiols [4]. Rink acid resin has also been converted to a trifluoroacetate with TFA and used in a similar manner to immobilize amines, thiols, alcohols, and phenols [5]. In a more detailed study, the same authors found 1 M trifluoroacetic anhydride in 2,6-lutidine to give superior results with less degradation of the linker [6, 7]. Rink resin trifluoroacetate has also been used to prepare purines [8, 9].Cleavage of amines and alcohols from this support has been carried out with either 5% TFA in DCM [4] or 20% TFA in DCM [5]; thiols were released with either 5% TFA in DCM [4] or 95% aq. TFA [5].

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

Literature references

[1] H. Rink (1987) Tetrahedron Lett., 28, 3787.
[2] H. U. Immer, et al. in ′Peptides, Chemistry, Structure &Biology, Proc. 11th American Peptide Symposium′, J. E. Rivier & G. R. Marshall (Eds), ESCOM, Leiden, 1990, pp. 1054.
[3] S. L. Mellor & W. C. Chan (1997) J. Chem. Soc., Chem. Commun., 2005.
[4] R. S. Garigipati (1997) Tetrahedron Lett., 38, 6807.
[5] W.K.-D. Brill in ′First Conference on Synthetic Organic Chemistry′, www.mdpi.org/ecsoc, 1997.
[6] W.K.-D. Brill (1998) Syn. Lett., 906.
[7] R. A. Tommesi, et al. (1998) Tetrahedron Lett., 39, 5477.
[8] W.K.-D. Brill (2001) Syn. Lett., 1097.
[9] W.K.-D. Brill & C. Riva-Toniolo (2001) Tetrahedron Lett., 42, 65`5.

Linkage

Replaces: 01-64-0012

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): beads
Loading (determined from the substition of the Fmoc-NH2 loaded resin): 0.35 - 0.80 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


Certificates of Analysis (COA)

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Articles

Novabiochem® has one of the most extensive ranges of linkers and derivatized resins for Fmoc solid phase peptide synthesis. These resins have varied properties with special protocols for loading and cleaving.

Protocols

Review methods and resins for attaching amino acids and peptides, including Merrifield, trityl-based, and hydroxymethyl-functionalized resins. Resin-immobilized peptides can be used for various downstream applications.

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