53907-28-1Relevant articles and documents
Visible-Light-Mediated S?H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow
Chen, Lin,Cui, Yu-Sheng,Duan, Xiu,Guo, Kai,Qin, Long-Zhou,Qiu, Jiang-Kai,Sun, Qi,Yuan, Xin,Zhuang, Kai-Qiang
, p. 5093 - 5104 (2020/09/23)
We describe the application of S?H bond insertion reactions of aryl diazoacetates with cysteine residues that enabled metal-free, S?H functionalization under visible-light conditions. Moreover, this process could be intensified by a continuous-flow photomicroreactor on the acceleration of the reaction (6.5 min residence time). The batch and flow protocols described were applied to obtain a wide range of functionalized cysteine derivatives and cysteine-containing dipeptides, thus providing a straightforward and general platform for their functionalizations in mild conditions. (Figure presented.).
A new efficient method for S-CH2-S bond formation and its application to a djenkolic acid-containing cyclic enkephalin analog
Ueki, Masaaki,Ikeo, Takayoshi,Hokari, Kumiko,Nakamura, Keiko,Saeki, Akihiko,Komatsu, Hiroshi
, p. 829 - 838 (2007/10/03)
An efficient methylene insertion reaction to construct an S-CH2-S bridge between two cysteine residues occurred when the thiol-protecting dimethylphosphinothioyl (Mpt) group of Z-Cys(Mpt)-OMe was removed with tetrabutylammonium fluoride hydrate in CH2Cl2. The thiol-free form gave similar results, albeit the yields were somewhat lower. In both cases, the best yields were obtained using 2 molar amounts of the reagent. Higher amounts of the reagent reduced the yield because of dehydroalanine formation. In the case of penicillamine, the thiol-free form was better in reactivity than the S-Mpt form, which required double the amount of the reagent to give the same yield. The reaction was successfully used in a synthesis of a cyclic enkephalin analog with the S-CH2-S bridge.
Synthesis and conformations of α-aminoadipyl- and glycyl-α-aminoadipylthiazepine sulfoxides
Wolfe,Bowers,Hasan,Kazmaier
, p. 406 - 421 (2007/10/02)
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