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Updated: May 3, 2026

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Synthetic Methodology for Asymmetric Ferrocene Derived Bio-conjugate Systems via Solid Phase Resin-based Methodology

Published on: March 12, 2015

Serine-Selective Bioconjugation.

Julien C Vantourout¹, Srinivasa Rao Adusumalli², Kyle W Knouse¹

¹Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Journal of the American Chemical Society

|September 23, 2020

Summary

This summary is machine-generated.

Researchers developed a new method for modifying serine residues in proteins. This approach allows for attaching various molecules to serine, creating stable linkages and expanding bioconjugation techniques.

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Published on: March 6, 2019

Area of Science:

Biochemistry
Organic Chemistry
Chemical Biology

Background:

Site-selective bioconjugation is crucial for developing novel protein-based therapeutics and diagnostics.
Existing methods often lack generality, chemoselectivity, or require complex protecting group strategies.
Functionalization of serine residues in native polypeptides presents unique challenges due to its nucleophilic nature and prevalence.

Purpose of the Study:

To report the first general method for rapid, chemoselective, and modular functionalization of serine residues in native polypeptides.
To introduce a novel reagent platform based on the P(V) oxidation state for protein modification.
To expand the toolbox of site-selective bioconjugation methods for diverse applications.

Main Methods:

Utilized a reagent platform based on the phosphorus(V) oxidation state.
Developed a redox-economical approach for appending cargo molecules to serine residues.
Demonstrated tolerance to all other known nucleophilic functional groups of proteinogenic amino acids.

Main Results:

Achieved rapid, chemoselective, and modular functionalization of serine residues in native polypeptides.
Generated a stable, benign, and hydrophilic phosphorothioate linkage.
Successfully appended a wide range of cargo molecules onto serine.

Conclusions:

The reported method offers a versatile and efficient strategy for serine functionalization.
This advancement significantly expands the possibilities for site-selective bioconjugation.
The developed approach holds promise for various applications in chemical biology and drug development.