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. Author manuscript; available in PMC: 2020 Jun 12.
Published in final edited form as: J Am Chem Soc. 2020 May 5;142(20):9112–9118. doi: 10.1021/jacs.0c03039

Table 1.

Selected Optimization

graphic file with name nihms-1596383-t0007.jpg
Entry [2] μM [1] mM Buffera Additive t (min) Conversion of 2b %2a (mono/di)b
1 100 10 NH4OAc 30 >95% 34% (>20:1)
2 100 7   NH4OAc 30 >95% 27% (>20:1)
3 100 7   NH4OAc 1 mM GSH 30 >95% 95% (>20:1)
4 10   7   NH4OAc 1 mM GSH 30 >95% 95% (>20:1)
5 100 7   Na2HPO4 1 mM GSH 45 >95% <95% (3:1)  
6 100 7   NaOAc    1 mM GSH 30 >95% 95% (>20:1)
7c 100 7   NH4OAc 1 mM GSH 30 0%     0%
a

[Buffer] = 20 mM. NH4OAc: pH = 6.9. Na2HPO4: pH = 7.4. NaOAc: pH = 8.9.

b

Estimated by LC-MS TIC, average of 2 runs.

c

Reaction was performed in the dark.