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. 2019 Aug 29;10(41):9506–9512. doi: 10.1039/c9sc04028e

Table 1. Oxime ligation conversions (%) determined by LCMS after 24 h.

Inline graphic
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