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. 2015 Apr 13;6(6):3329–3333. doi: 10.1039/c5sc00921a

Table 2. Tolerance of the condensation to biological interfering agents.

Inline graphic
Entry Additive (conc) Normalized 2a integral b (%) Significance
1 None 100
2 Glutathione (5 mM) 98 Biothiols do not interfere
3 Sucrose (100 µM & 5 mM) 106/92 c Boron chelators do not interfere
4 Lysozyme (100 µM) 105 Amino acid side-chains cannot compete with O-alkylhydroxylamine for 2-FPBA
5 Human serum (20% v/v) 80 d Reaction is compatible with complex media

aTime is approximate since samples are injected directly after mixing.

bDetermined by reverse phase HPLC analysis under neutral conditions.

cThis reaction was also performed by pre-mixing the boronic acid with the sucrose, with no measurable change in conjugation efficiency.

dHuman serum leads to oxidation of the boronic acid to a phenol by a Baeyer–Villiger type reaction. The 80% number represents only the measurement of 2a, when the phenol is included nearly complete mass balance is observed. KPi = potassium phosphate buffer.