New chemistry of S-nitrosothiols
Protein S-nitrosation is an important post-translational modification that not only transmits nitric oxide (NO) biological activity, but also regulates protein functions. However, development of reliable methods for the detection of protein S-nitrosation is still a challenge due to the lability of its products S-nitrosothiols (SNOs). The thesis will discuss three aspects in detail: first, the development of fluorescent probes for the detection of SNOs based on the reductive ligation; second, the study on the reactivity of sulfenamides which is the reductive ligation product from SNOs, towards different nucleophiles, and further development of a one-pot disulfide formation reaction; lastly, the synthetic application of S-nitrosation in amide/peptide synthesis. The new chemistry of S-nitrosothiols not only provides a promising platform for the study of S-nitrosation in biological system, but also reveals the potential usage of S-nitrosation in organic synthesis.