Table 1. Oxime ligation conversions (%) determined by LCMS after 24 h.
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Entry | Peptides | % Oxime at t = 24 h |
1 | 2a: R1 = H, R2 = NMe2 | >99 a |
2 | 2b: R1 = CH3, R2 = NMe2 | 94 a |
3 | 2c: R1 = Ph, R2 = NMe2 | 99 a |
4 | 2d: R1 = CH2Ph, R2 = NMe2 | 69 a |
5 | 3a: R1 = H, R2 = OMe | <1 a (72 b ) |
6 | 3b: R1 = CH3, R2 = OMe | <1 a (<1 b ) |
7 | 3c: R1 = Ph, R2 = OMe | <1 a (<1 b ) |
8 | 3d: R1 = CH2Ph, R2 = OMe | <1 a (<1 b ) |
aReactions were performed in phosphate buffer pH 7 under an O2 atmosphere with 5 mM O-benzylhydroxylamine hydrochloride and 1 mM peptide concentrations.
bReactions were performed in ammonium acetate buffer pH 4.5 under air with 1 mM O-benzylhydroxylamine hydrochloride and 1 mM peptide concentrations.13