| Entry | A | A′ | B | B′ | A′ + B′ | ||
|---|---|---|---|---|---|---|---|
| Sequence | Sequence | % | Sequence | Sequence | % | % | |
| 20 | H-SD′LSQRG-SAL ester |
|
>98a, 48.0b | Boc-(Thz)(K–S)LSQRG-SAL ester |
|
88.9b, 37.2d | 84.3b, 50.4c |
| 21 | Boc-(Thz)NFS(K–S)QSNKRFLSKTQG-SAL ester |
|
90.1b, 35.4d | 89.9b, 45.8c | |||
D′ = Asp(benzofuran), (K–S) = Lys–Ser dipeptide, SAL = salicylaldehyde.
Percentage conversion to the ligation product based on UPLC-MS analysis of the crude reaction mixture.
Isolated yield based on ligation.
Isolated yield over 2 steps (intramolecular STL and one-pot Thz deprotection).
Isolated yield over 2 steps (intramolecular STL and one-pot Fmoc deprotection).