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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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Cyclization of peptide b9 ions.

Alex G Harrison¹

¹Department of Chemistry, University of Toronto, Toronto, ON, Canada. aharriso@chem.utoronto.ca

Journal of the American Society for Mass Spectrometry

|September 29, 2009

Summary

Peptide fragmentation via collision-induced dissociation (CID) reveals a common intermediate in cyclization reactions. N-terminal acetylation prevents this cyclization, eliminating non-direct sequence ions in mass spectra.

Area of Science:

* Analytical Chemistry
* Biochemistry
* Mass Spectrometry

Background:

* Peptide fragmentation analysis using mass spectrometry is crucial for protein sequencing and characterization.
* Collision-induced dissociation (CID) is a common technique for peptide fragmentation.
* Understanding fragmentation pathways, including cyclization reactions, is essential for accurate interpretation of mass spectra.

Purpose of the Study:

* To investigate the fragmentation patterns of specific tyrosine-containing peptides (Tyr(Ala)9, (Ala)4Tyr(Ala)5, and (Ala)8TyrAla) using CID.
* To determine if a common intermediate is formed during the cyclization of these peptides.
* To assess the impact of N-terminal acetylation on peptide cyclization and subsequent fragmentation.

Main Methods:

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* Analysis of product ion mass spectra obtained by CID of b(9) and b(8) ions.
* Comparison of mass spectra from different peptide sequences to identify common fragmentation patterns.
* Investigation of the effect of N-terminal acetylation on fragmentation pathways.

Main Results:

* Product ion mass spectra of b(9) ions from Tyr(Ala)9, (Ala)4Tyr(Ala)5, and (Ala)8TyrAla were nearly identical, suggesting a common cyclized intermediate.
* Abundant non-direct sequence ions were observed in the b(9) ion spectra, supporting the cyclization hypothesis.
* N-terminal acetylation effectively blocked cyclization, leading to the absence of non-direct sequence ions.

Conclusions:

* CID fragmentation of these peptides indicates a complete cyclization reaction to a common intermediate prior to fragmentation.
* The presence of non-direct sequence ions is a marker for this cyclization pathway.
* N-terminal acetylation serves as a protective strategy against unwanted cyclization during mass spectrometric analysis.