Fmoc-Leu-Wang Resin

Fmoc-Leu-Wang Resin
Nα-Fmoc-L-leucine esterified to Wang (4-alkoxybenzyl alcohol) resin; 100–200 mesh, 0.3–0.8 mmol/g

Wang resin preloaded with Fmoc-Leu-OH, for making peptide acids with a C-terminal leucine 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.

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. 2-Chlorotrityl resin can reduce the loss for such sequences, though not eliminate it.

Applications

• Peptide acids with a C-terminal leucine
• Hydrophobic and helical sequences
• 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. Fields GB et al. Solid phase peptide synthesis utilizing 9‐fluorenylmethoxycarbonyl amino acids. International Journal of Peptide and Protein Research 1990, 35, 161–214. doi:10.1111/j.1399-3011.1990.tb00939.x
3. Pedroso E et al. Diketopiperazine formation in solid phase peptide synthesis using p-alkoxybenzyl ester resins and Fmoc-amino acids. Tetrahedron Letters 1986, 27, 743–746. doi:10.1016/s0040-4039(00)84089-7

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