Electrophilic substitution reaction of benzeneselenyl bromide (chloride) for the selective modification of tryptophan side chain in peptides

Yuewen Tan; Yangyang Zhang; Nan Yang; Jiawei Wang; Changying Song; Ruotong Liang; Shigang Shen; Shuying Huo

doi:10.1039/d6cc00983b

January 1, 2026Chemical Communications

Electrophilic substitution reaction of benzeneselenyl bromide (chloride) for the selective modification of tryptophan side chain in peptides

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Key Points

This research aims to develop a method for site-selective phenylselenylation of tryptophan in peptides.
Conducted phenylselenylation of C2 site of indole ring in tryptophan residues.
Utilized an acidic aqueous medium without metal catalysts.
Applied the method to various peptide structures.
Successfully modified the C2 site of the indole ring in tryptophan.
Achieved site selectivity in the presence of various peptides.
Demonstrated the reaction was effective without the use of metal catalysts.

Implication

Novel electrophilic substitution modifies tryptophan in peptides, suggesting a new approach for achieving site-selective reactions.

Abstract

A novel site-selective phenylselenylation of C2 site of indole ring in the Trp side chain of various peptides was achieved in an acidic aqueous medium without metal catalysts via an...

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Cite This Study

Tan et al. (2026) studied this question.

synapsesocial.com/papers/69ccb6fd16edfba7beb88c11 https://doi.org/10.1039/d6cc00983b

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Electrophilic substitution reaction of benzeneselenyl bromide (chloride) for the selective modification of tryptophan side chain in peptides

Key Points

Implication

Abstract

Discussion

Cite This Study

Electrophilic substitution reaction of benzeneselenyl bromide (chloride) for the selective modification of tryptophan side chain in peptides

Key Points

Implication

Abstract

Discussion

Cite This Study

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