Table 1 Aromatic and aliphatic thiol pKa values and corresponding yields in N–O bond cleavage assays.
From: Aromatic thiol-mediated cleavage of N–O bonds enables chemical ubiquitylation of folded proteins
Entry | Thiol | Yield (%) | |
|---|---|---|---|
1 | 4-Nitrothiophenol | 4.5 | 59 |
2 | 3-Mercaptobenzoic acid | 5.8 | 81 |
3 | 4-Mercaptophenylacetic acid | 6.6 | 73 |
4 | 4-Aminothiophenol | 6.9 | 73 |
5 | 4-Hydroxythiophenol | 7.0 | n.d. |
6 | 2,2,2-Trifluoroethanethiol | 7.6 | n.d. |
7 | L-Glutathione | 9.1 | n.d. |
8 | D,L-Dithiothreitol | 9.2, 10.1 | n.d. |
9 | 2-Mercaptoethanesulfonic acid | 9.2 | n.d. |
10 | 2-Methyl-2-propanethiol | 11.2 | n.d. |
