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Total solid-phase synthesis of NOTA-functionalized peptides for PET imaging.

Brigitte Guérin¹, Samia Ait-Mohand, Marie-Claude Tremblay

¹Centre d'imagerie moléculaire de Sherbrooke (CIMS), Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, Université de Sherbrooke, 3001, 12th Avenue North, Sherbrooke, Québec, Canada J1H 5N4. brigitte.guerin2@usherbrooke.ca

Organic Letters

|December 18, 2009

Summary

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A new solid-phase method simplifies peptide functionalization with the 1,4,7-triazacyclononane-N,N

Area of Science:

Medicinal Chemistry
Organic Synthesis
Bioconjugation Chemistry

Background:

Peptide functionalization is crucial for developing novel therapeutics and diagnostic agents.
Incorporating metal chelators like 1,4,7-triazacyclononane-N,N',N''-triacetic acid (NOTA) enables radiolabeling for imaging and therapy.
Existing methods for NOTA conjugation can be complex and inefficient.

Purpose of the Study:

To develop a convenient and efficient solid-phase method for conjugating the NOTA chelator to peptides.
To enable functionalization at either the N-terminus or a lysine side chain.
To provide a versatile platform for creating NOTA-conjugated peptides for various applications.

Main Methods:

Solid-phase synthesis approach.

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Two-step assembly process starting with bromo-acetylated peptides.

Deprotection and cleavage using trifluoroacetic acid (TFA) with scavengers.

Main Results:

Successful functionalization of peptides with the NOTA chelating unit at defined positions (N-terminal or lysine side chain).
Demonstration of a convenient two-step solid-phase assembly.
Efficient deprotection and cleavage yielding free NOTA-conjugated peptides.

Conclusions:

The developed solid-phase method offers a convenient and efficient route to NOTA-functionalized peptides.
This approach facilitates the preparation of peptides for applications requiring metal chelation, such as radiopharmaceuticals.
The method provides a valuable tool for peptide-based drug discovery and diagnostics.