Table 1.

Selective oxidations of solid supported N-terminal peptide amines with 1 and subsequent ligations.^a

Entry	AA1 =	Ligation product	Product peak areac / %	Mass yield (from resin)	Isolated yieldd / %
1	Ser	Fmoc-Phe–Ser-Asp-Tyr-Lys-Ala-NH2	55% (220 nm)	4.8 mg from 49.4 mg 12a	22
2b	Ser	Fmoc-Phe–Ser-Asp-Tyr-Lys-Ala-NH2	37% (220 nm)	not determined	not determined
3	Glu	Fmoc-Phe–Glu-Asp-Tyr-Lys-Ala-NH2	41% (220 nm)	6.8 mg from 6.2 mg 12b	25
4	Phe	Fmoc-Phe–Phe-Asp-Tyr-Lys-Ala-NH2	42% (220 nm)	5.1 mg from 64.6 mg 12c	17
5	Ala	Fmoc-Phe–Ala-Asp-Tyr-Lys-Ala-NH2	47% (220 nm)	2.9 mg from 32.9 mg 12d	18
6	Leu	Fmoc-Phe–Leu-Lys-Ser-Glu-Tyr-NH2	31% (220 nm)	3.4 mg from 38.7 mg 12e	20

^aSee Supporting Information for further experimental details.

^b(±)-1 was used.

^cDetermined by HPLC analyses of unpurified peptides following cleavage.

^dApproximate yields over entire sequence based on mass recovery of the ligated peptide following preparative HPLC.