28792-97-4Relevant articles and documents
H2O-Regulated Chemoselectivity in Oxa- Versus Aza-Michael Reactions
Huang, Rong,Li, Zhihong,Yu, Jianghui,Chen, Hongli,Jiang, Biao
, p. 4159 - 4162 (2019)
A H2O-regulated chemoselective addition in oxa- and aza-Michael reactions for aminoalcohols and mixtures of structurally similar alcohols and amines was reported. The oxa-Michael reactions might be kinetically controlled, and the reactions to produce O-selective products were slowed by the addition of water. The electrophilicity of Michael acceptors and the steric hindrance of Michael donors also affect the ratios of O/N products. This method offers novel ideas over conventional metal-catalyzed or ligand-induced strategies.
Visible-Light-Promoted Radical Cyclization of N -Arylvinylsulfonamides: Synthesis of CF 3/CHF 2/CH 2CF 3-Containing 1,3-Dihydrobenzo[ c ]isothiazole 2,2-Dioxide Derivatives
Vytla, Devaiah,Kaliyaperumal, Kumargurubaran,Velayuthaperumal, Rajeswari,Shaw, Parinita,Gautam, Raj,Mathur, Arvind,Roy, Amrita
supporting information, p. 667 - 682 (2021/11/13)
A photocatalyzed and highly efficient trifluoromethylation of N-arylvinylsulfonamides using commercially available CF3SO2Cl as the trifluoromethyl radical source under blue LEDs is reported. The reaction proceeds through radical cyclization under mild con
N-Phenyl-N-aceto-vinylsulfonamides as Efficient and Chemoselective Handles for N-Terminal Modification of Peptides and Proteins
Huang, Rong,Li, Zhihong,Ren, Peiling,Chen, Wenzhang,Kuang, Yuanyuan,Chen, Jiakang,Zhan, Yuexiong,Chen, Hongli,Jiang, Biao
supporting information, p. 829 - 836 (2018/02/21)
A number of vinylsulfonamides were synthesized and screened to identify reagents that can be used to modify octreotide under biological pH and room temperature with improved efficiency. N-Phenyl-N-aceto-vinylsulfonamide exhibits higher reactivity and has emerged as an efficient reagent that has the ability to realize the selective modification of peptides and proteins at the N-terminus via aza-Michael addition. We showed that, after conjugation of peptides and proteins with the reagent containing a bioorthogonal functional group, the derivatives could be further labelled by functionalities, including fluorescent tags, modified drugs and polyethylene glycol (PEG) polymers without the need for prior treatment. Somatostatin, lysozyme, and RNaseA were selectively modified at the N-terminus, which illustrated the application of the method.
