Fmoc-Gln(Trt)-Wang Resin

Fmoc-Gln(Trt)-Wang Resin
Nα-Fmoc-Nδ-trityl-L-glutamine esterified to Wang (4-alkoxybenzyl alcohol) resin; 100–200 mesh, 0.3–0.8 mmol/g

Wang resin preloaded with Fmoc-Gln(Trt)-OH, for making peptide acids with a C-terminal glutamine 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. Include TIS to trap the trityl cation released from the glutamine side chain. The loading for each lot is on its certificate of analysis.

At the dipeptide stage the free amine can attack the ester bond to the resin and leave as a diketopiperazine. This is most likely when proline or glycine is one of the first two residues; couple the third residue promptly after the second Fmoc removal, or start on 2-chlorotrityl resin for such sequences.

Applications

• Peptide acids with a C-terminal glutamine
• Manual and automated synthesis
• Peptide libraries and parallel 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. Sieber P et al. Protection of carboxamide functions by the trityl residue. Application to peptide synthesis. Tetrahedron Letters 1991, 32, 739–742. doi:10.1016/s0040-4039(00)74872-6

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