Rink Amide (RAM) Resins

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

Materials
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References

1.
Atherton E, Clive DLJ, Sheppard RC. 1975. Polyamide supports for polypeptide synthesis. J. Am. Chem. Soc.. 97(22):6584-6585. http://dx.doi.org/10.1021/ja00855a053
2.
Albericio F, Kneib-Cordonier N, Biancalana S, Gera L, Masada RI, Hudson D, Barany G. 1990. Preparation and application of the 5-(4-(9-fluorenylmethyloxycarbonyl)aminomethyl-3,5-dimethoxyphenoxy)-valeric acid (PAL) handle for the solid-phase synthesis of C-terminal peptide amides under mild conditions. J. Org. Chem.. 55(12):3730-3743. http://dx.doi.org/10.1021/jo00299a011
3.
ALBERICIO F, BARANY G. Acidolytic cleavage of tris(alkoxy)benzylamide (PAL) ?internal reference? amino acyl (IRAA) anchoring linkages: validation of accepted procedures in solid-phase peptide synthesis (SPPS). 41(3):307-312. http://dx.doi.org/10.1111/j.1399-3011.1993.tb00339.x
4.
Rink H. 1987. Solid-phase synthesis of protected peptide fragments using a trialkoxy-diphenyl-methylester resin.. Tetrahedron Letters. 28(33):3787-3790. http://dx.doi.org/10.1016/s0040-4039(00)96384-6
5.
Bernatowicz MS, Daniels SB, Köster H. 1989. A comparison of acid labile linkage agents for the synthesis of peptide C-terminal amides. Tetrahedron Letters. 30(35):4645-4648. http://dx.doi.org/10.1016/s0040-4039(01)80764-4
6.
Breipohl G, Knolle J, Geiger R. 1987. Solid phase synthesis of peptide aminoalkylamides development and application of new linking agents. Tetrahedron Letters. 28(46):5647-5650. http://dx.doi.org/10.1016/s0040-4039(00)96803-5

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