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

doi:10.1021/ol200793z

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 journal › Article › peer-review

27 Scopus citations

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 language	English (US)
Pages (from-to)	2837-2839
Number of pages	3
Journal	Organic Letters
Volume	13
Issue number	11
DOIs	https://doi.org/10.1021/ol200793z
State	Published - Jun 3 2011
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol200793z

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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.",

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language = "English (US)",

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T1 - Neighboring pyrrolidine amide participation in thioether oxidation. methionine as a "hopping" site

AU - Glass, Richard S.

AU - Schöneich, Christian

AU - Wilson, George S.

AU - Nauser, Thomas

AU - Yamamoto, Takuhei

AU - Lorance, Edward

AU - Nichol, Gary S.

AU - Ammam, Malika

PY - 2011/6/3

Y1 - 2011/6/3

N2 - 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.

AB - 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.

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JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

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

Abstract

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CCDC 843943: Experimental Crystal Structure Determination

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

Abstract

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Datasets

CCDC 843943: Experimental Crystal Structure Determination

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