The photochemistry of N-p-toluenesulfonyl peptides: the peptide bond as an electron donor

Hill, Roger R.; Moore, Sharon A. and Roberts, David R. (2005). The photochemistry of N-p-toluenesulfonyl peptides: the peptide bond as an electron donor. Photochemistry and Photobiology, 81(6) pp. 1439–1446.

DOI: https://doi.org/10.1562/2005-04-29-RA-507

Abstract

The scope of photobiological processes that involve absorbers within a protein matrix may be limited by the vulnerability of the peptide group to attack by highly reactive redox centers consequent upon electronic excitation. We have explored the nature of this vulnerability by undertaking comprehensive product analyses of aqueous photolysates of 12 N-p-toluene-sulfonyl peptides with systematically selected structures. The results indicate that degradation includes a major pathway that is initiated by intramolecular electron transfer in which the peptide bond serves as electron donor, and the data support the likelihood of a relay process in dipeptide derivatives.

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About

• Item ORO ID
• 3684
• Item Type
• Journal Item
• ISSN
• 0031-8655
• Keywords
• alpha-amino-acids; cleavage reactions; distance dependence; Alzheimers disease; protecting groups; aqueous alkali; oxidation; sulfonamides; mechanism; photodegradation
• Academic Unit or School
• Faculty of Science, Technology, Engineering and Mathematics (STEM) > Life, Health and Chemical Sciences
  Faculty of Science, Technology, Engineering and Mathematics (STEM)
• Depositing User
• David R. Roberts