Peptide scope of N–H cross-couplinga.
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Entry | Peptide (sulfoximine) | Yieldb (%) |
1 | Ac-MGDFQ-NH2 | 94 |
2 | Ac-MGKFQ-NH2 | 61 |
3 | Ac-YGMLNP-NH2 | 40 |
4 | Ac-VGMSWP-NH2 | 75 |
5 | Ac-FPQSGM-NH2 | 50 |
6 | Ac-MGRFTINP-NH2 | 76 |
7 | Ac-RPKPQQFFGLM-NH2 (substance P) | 50 |
8 | Ac-SYSMEHFRWGKPV-NH2 (α-MSH) | 51 |
Conditions: methionine sulfoximine-containing peptides (1b–8b) (0.2 mM), 4-nitrophenylboronic acid (4 mM), and Cu(OAc)2 (1 mM) in MeOH at room temperature for 16 h.
Yield calculated by RP-HPLC.