Table 8. Z-Selective RCM to form i, i + 4 Stapled Peptides.
| conversionb,c (%) |
Z selectivityd (%) |
||||||
|---|---|---|---|---|---|---|---|
| entry | catalyst (mol %) | resina | time (h) | 1 | 2 | 1 | 2 |
| 1 | 10 | Wang | 2 | 25 | 20 | n.d. | n.d. |
| 2 | 10 | TentaGel | 2 | 40 | 30 | n.d. | n.d. |
| 3 | 10 | MBHA | 2 | 60 | 55 | n.d. | n.d. |
| 4 | 10 | MBHA | 4 | 70 | 60 | >85 | >90 |
| 5 | 10 (×2) | MBHA | 4 | 75 | 75 | >85 | >90 |
| 6 | 10 (×2) | MBHA | 4 | 80e | 70 | >85 | >90 |
a
Loading capacities for resin: Wang, 0.5 mmol/g; TentaGel, 0.25 mmol/g; MBHA, 0.5 mmol/g.
b
Conversions determined by analytical HPLC of cleaved peptide.
c
Amino acids were protected prior to RCM.
d
Determined by analytical HPLC-MS.
e
Reaction carried out at 40 °C.