Rink Amide (RAM) Resins

ChemFiles Volume 3 Article 4

A broad variety of 4-((2,4-dimethoxyphenyl)(Fmoc-amino)methyl)phenoxyalkyl functionalized supports have been developed for the synthesis of peptide carboxamides.(1, 2) Detachment of peptide amides from these widely used supports can be achieved by treatment with 95% trifluoroacetic acid (TFA). Lability of the benzyl phenyl ether linkage towards high concentrations of TFA was associated with by-product formation during final cleavage from the original Rink amide resin 4-((2,4-dimethoxyphenyl)(Fmocamino) methyl)phenoxymethylpolystyrene. All Rink amide resins supplied by us are therefore functionalized with the modified Rink amide (RAM) linker: 4-((2,4-dimethoxyphenyl)(Fmoc-amino)methyl)phenoxyacetic acid.(2) Aminomethylpolystyrene acylated with the RAM linker, also known as “Knorr” resin, is an excellent tool for SPPS of peptide amides. The C-terminal amino acid residue can be coupled using standard amide-forming procedures employing diisopropylcarbodiimide/hydroxybenzotriazole (HOBt) or uronium or phosphonium salts such as TBTU or BOP. The use of N-alkyl Rink resin can provide N-alkylamide peptides.(3)

PRODUCTS: 83896, 81554, 83886,
                        83901, 83891, 81560.

 

PRODUCTS: 83898, 83888,
                        86342, 79028.

 

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Materials

     

References

  1. Atherton, E. et al. J. Am. Chem. Soc. 1975, 97, 6584.
  2. Albericio, F. et al. J. Org. Chem. 1990, 55, 3730.
  3. Albericio, F.; Barany, G. Int. J. Pept. Protein Res. 1993, 41, 307.
  4. Rink, H. Tetrahedron Lett. 1987, 28, 3787.
  5. Bernatowicz, M.S. et al. Tetrahedron Lett. 1989, 30, 4645. 
  6. Breipohl, G. et al. Tetrahedron Lett. 1987, 28, 5647.

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