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Synfacts 2020; 16(12): 1487
DOI: 10.1055/s-0040-1719507
DOI: 10.1055/s-0040-1719507
Peptide Chemistry
Visible-Light-Mediated Functionalization of Cysteine Derivatives and Cysteine-Containing Peptides
Qin L.-Z,
Yuan X,
Cui Y.-S,
Sun Q,
Duan X,
Zhuang K.-Q,
Chen L,
Qiu J.-K,
*,
Guo K.
*
Nanjing Tech University, P. R. of China
Visible-Light-Mediated S–H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow.
Adv. Synth. Catal. 2020;
DOI: 10.1002/adsc.202000716.
Visible-Light-Mediated S–H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow.
Adv. Synth. Catal. 2020;
DOI: 10.1002/adsc.202000716.
Key words
cysteines - amino acid functionalization - peptide functionalization - diazoalkanes - S–H bond insertion - photochemical reaction
Significance
Functionalization of amino acids and peptides is a powerful synthetic tool in the field of peptide drug discovery. The authors have developed a visible-light-mediated S–H bond alkylation of cysteine derivatives and cysteine-containing peptides.
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Comment
The visible-light-mediated S–H bond insertion reaction of cysteine derivatives or cysteine-containing dipeptides with diazoalkanes proceeded smoothly to afford a series of alkylated cysteine derivatives and cysteine-containing peptides in satisfactory yields. Moreover, this method was also extended to a continuous-flow technique.
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Publication History
Article published online:
17 November 2020
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