Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides.

Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Research Abstract Details 

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Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Abstract Text:

Saiful M Chowdhury,Gerhard R Munske,Robert C Ronald,James E Bruce,

Thio-ether bonds in the cysteinyl side chain of peptides, formed with the most commonly used cysteine blocking reagent iodoacetamide, after conversion to sulfoxide, releases a neutral fragment mass in a low-energy MS/MS experiment in the gas phase of the mass spectrometer [6]. In this study, we show that the neutral loss fragments produced from the mono-oxidized thio-ether bonds (sulfoxide) in peptides, formed by alkyl halide or double-bond containing cysteine blocking reagents are different under low-energy MS/MS conditions. We have evaluated the low-energy fragmentation patterns of mono-oxidized modified peptides with different cysteine blocking reagents, such as iodoacetamide, 3-maleimidopropionic acid, and 4-vinylpyridine using FTICR-MS. We propose that the mechanisms of gas-phase fragmentation of mono-oxidized thio-ether bonds in the side chain of peptides, formed by iodoacetamide and double-bond containing cysteine blocking reagents, maleimide and vinylpyridine, are different because of the availability of acidic beta-hydrogens in these compounds. Moreover, we investigated the fragmentation characteristics of mono-oxidized thio-ether bonds within the peptide sequence to develop novel mass-spectrometry identifiable chemical cross-linkers. This methionine type of oxidized thio-ether bond within the peptide sequence did not show anticipated low-energy fragmentation. Electron capture dissociation (ECD) of the side chain thio-ether bond containing oxidized peptides was also studied. ECD spectra of the oxidized peptides showed a greater extent of peptide backbone cleavage, compared with CID spectra. This fragmentation information is critical to researchers for accurate data analysis of this undesired modification in proteomics research, as well as other methods that may utilize sulfoxide derivatives.

Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Publishing Authors By Initials

SM Chowdhury,GR Munske,RC Ronald,JE Bruce,

For similar investigative techniques: chemistry, analytical: mass spectrometry: tandem mass spectrometry research abstracts see: investigative techniques: chemistry, analytical: mass spectrometry: tandem mass spectrometry research

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Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Society for Mass Spectrome

VOLUME: 18

Page Numbers: 493-501

Journal Abbreviation: J. Am. Soc. Mass Spectrom.

ISSN: 1044-0305

DAY: 27

MONTH: 11

YEAR: 2006

Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Information

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LANGUAGE: eng

NlmUniqueID: 9010412

Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Keywords Mesh Terms:

KEYWORDS: Tandem Mass Spectrometry

MESH TERMS: chemistry

Chemical & Substance for Abstract: Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides. Information

Substance Name: Peptides

Registry Number: 0

Grant and Affiliation Information for Evaluation of low energy CID and ECD fragmentation behavior of mono-oxidized thio-ether bonds in peptides.

AFFILIATION: Department of Chemistry, Washington State University, Pullman, Washington 99164-4630, USA.

Country: United States

AGENCY: United States NCRR

GRANT: S10 RR022538-01

ACRONYM: RR

MEDLINETA: J Am Soc Mass Spectrom

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