Skip to main content
. Author manuscript; available in PMC: 2019 Sep 18.
Published in final edited form as: Acc Chem Res. 2018 Aug 15;51(9):2198–2206. doi: 10.1021/acs.accounts.8b00154

Figure 4.

Figure 4.

Fast bioorthogonal conjugation of 2-FPBA/APBA with α-nucleophiles. (a) Mechanistic illustration of the boronic acid-accelerated conjugation of 2-FPBA/APBA with α-nucleophiles. (b) Oxime formation of 2-FPBA and 2-APBA yielding distinct product stability. ND: Not Determined; NA: Not Applicable. Exchange is considered Not Applicable to highly dynamic reactions. (c) Stable diazaborine formation of 2-FPBA/APBA upon conjugation with phenylhydrazine. (d) Dynamic conjugation of 2-FPBA/APBA to carbohydrazides. (e) Stable diazaborine formation of 2-FPBA/APBA with semicarbazide. (f) Crystal structure of a diazaborine conjugate of 2-FPBA and semicarbazide. (g) Improving the conjugate stability of carbohydrazide with an α-amino group that forges additional B-N bond.