Precise late modification of tryptophan residues in natural peptides

The use of sulfenyl reagents for C2-sulfenylation of tryptophan residues in peptides addresses precision and efficiency issues in existing methods, enabling diverse functional group introduction and enhanced peptide stability for therapeutic use.

JP2026521679APending Publication Date: 2026-07-01VERSITECH LTD
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Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Applications
Current Assignee / Owner
VERSITECH LTD
Filing Date
2024-05-07
Publication Date
2026-07-01

AI Technical Summary

Technical Problem

Existing post-modification methods for tryptophan residues in peptides face challenges such as contamination by trace metal residues, long reaction times, elevated temperatures, and selectivity issues between tryptophan and other residues, limiting the precision and efficiency of peptide modifications.

Method used

A method using sulfenyl reagents, particularly thiosulfonic acid esters, for precise C2-sulfenylation of tryptophan residues in peptides, allowing introduction of diverse functional groups under mild conditions, avoiding trace metals and achieving complete conversion within 2 hours at room temperature.

Benefits of technology

Enables precise and efficient modification of tryptophan residues in peptides, providing unprecedented diversity of functional groups and improved peptide stability and pharmacokinetics, suitable for therapeutic applications.

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Abstract

This specification describes a method for the late modification of peptides and functionalized peptides. The method is specific and robust and allows for the precise construction of C2-sulfenylated tryptophan using sulfenyl reagents such as thiosulfonic acid ester (ArSO2SR) reagents. This simple C2-sulfenylation process allows for the easy introduction of a variety of functional groups, such as SCF3, SCF2H, SCF2Br, SCHFCl, SCF2-alkyl groups, SCHF-alkyl groups, S-alkyl groups, and S-aryl groups, into peptides, particularly tryptophan residues of natural peptides. Generally, a late peptide modification method comprises (i) the step of maintaining a reaction mixture at a sufficient temperature for a sufficient time to produce a product. The reaction mixture comprises a peptide to be modified containing one or more tryptophan residues, a sulfenyl reagent, and a solvent. The product produced in step (i) comprises a sulfenylated peptide, wherein the sulfenylation has occurred in at least one of the one or more tryptophan residues of the peptide.
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