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Synfacts 2020; 16(12): 1487
DOI: 10.1055/s-0040-1719507
Peptide Chemistry

Visible-Light-Mediated Functionalization of Cysteine Derivatives and Cysteine-Containing Peptides

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
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
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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.


 

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.


 

 

Publication History

Article published online:
17 November 2020

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