Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site

Richard S Glass, Christian Schöneich, George S. Wilson, Thomas Nauser, Takuhei Yamamoto, Edward Lorance, Gary S. Nichol, Malika Ammam

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

Methionine residues have been shown to function as efficient "hopping" sites in long-range electron transfer in model polyprolyl peptides. We suggest that a key to this ability of methionine is stabilization of the transient sulfur radical cation by neighboring proline amide participation. That is, in a model system a neighboring pyrrolidine amide lowers the oxidation potential of the thioether by over 0.5 V by formation of a two-center three-electron SO bond.

Original languageEnglish (US)
Pages (from-to)2837-2839
Number of pages3
JournalOrganic Letters
Volume13
Issue number11
DOIs
StatePublished - Jun 3 2011

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methionine
Sulfides
Amides
Methionine
amides
Electrons
Oxidation
oxidation
Sulfur
Proline
peptides
Cations
electron transfer
sulfur
Stabilization
stabilization
cations
Peptides
electrons
pyrrolidine

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

Cite this

Glass, R. S., Schöneich, C., Wilson, G. S., Nauser, T., Yamamoto, T., Lorance, E., ... Ammam, M. (2011). Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site. Organic Letters, 13(11), 2837-2839. https://doi.org/10.1021/ol200793z

Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site. / Glass, Richard S; Schöneich, Christian; Wilson, George S.; Nauser, Thomas; Yamamoto, Takuhei; Lorance, Edward; Nichol, Gary S.; Ammam, Malika.

In: Organic Letters, Vol. 13, No. 11, 03.06.2011, p. 2837-2839.

Research output: Contribution to journalArticle

Glass, RS, Schöneich, C, Wilson, GS, Nauser, T, Yamamoto, T, Lorance, E, Nichol, GS & Ammam, M 2011, 'Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site', Organic Letters, vol. 13, no. 11, pp. 2837-2839. https://doi.org/10.1021/ol200793z
Glass, Richard S ; Schöneich, Christian ; Wilson, George S. ; Nauser, Thomas ; Yamamoto, Takuhei ; Lorance, Edward ; Nichol, Gary S. ; Ammam, Malika. / Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site. In: Organic Letters. 2011 ; Vol. 13, No. 11. pp. 2837-2839.
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