Fmoc-Arg(Pbf)-Wang Resin

Fmoc-Arg(Pbf)-Wang Resin
Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine esterified to Wang (4-alkoxybenzyl alcohol) resin; 100–200 mesh, 0.3–0.8 mmol/g

Wang resin preloaded with Fmoc-Arg(Pbf)-OH, for making peptide acids with a C-terminal arginine by Fmoc SPPS. Remove the Fmoc group with 20% piperidine in DMF and build the chain as usual; final cleavage with 95% TFA and scavengers releases the peptide acid and removes the side-chain protecting groups. The loading for each lot is on its certificate of analysis.

The Pbf group comes off in the same cleavage, typically 2–3 hours in 95% TFA with water and TIS; peptides with several arginines may need longer. Using Fmoc-Trp(Boc)-OH for any tryptophan in the sequence reduces its modification by Pbf by-products.

Applications

• Peptide acids with a C-terminal arginine
• Arginine-rich and cell-penetrating peptides
• Manual, microwave and automated synthesis

Storage
Store refrigerated (2–8 °C) and dry, in a tightly closed container.

References

1. Wang S. p-Alkoxybenzyl Alcohol Resin and p-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide Fragments. Journal of the American Chemical Society 1973, 95, 1328–1333. doi:10.1021/ja00785a602
2. Carpino LA et al. The 2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl group (Pbf) as arginine side chain protectant. Tetrahedron Letters 1993, 34, 7829–7832. doi:10.1016/s0040-4039(00)61487-9

For research use only. Not for human or veterinary use.