A picomole-scale method for charge derivatization of peptides for sequence analysis by mass spectrometry.
Identifieur interne : 003C33 ( Main/Exploration ); précédent : 003C32; suivant : 003C34A picomole-scale method for charge derivatization of peptides for sequence analysis by mass spectrometry.
Auteurs : Z H Huang [États-Unis] ; J. Wu ; K D Roth ; Y. Yang ; D A Gage ; J T WatsonSource :
- Analytical chemistry [ 0003-2700 ] ; 1997.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , analysis : Peptides.
- chemical , chemistry : Peptides.
- chemical : Indicators and Reagents.
- methods : Sequence Analysis.
- Amino Acid Sequence, Mass Spectrometry, Molecular Sequence Data.
Abstract
A highly activated ester containing a fixed positive charge, S-pentafluorophenyl [tris(2,4,6-trimethoxyphenyl)phosphonium]acetate bromide (TMPP-AcSC6F5 bromide), has been synthesized as a reagent for N-terminal modification of peptides. Stable in aqueous acetonitrile solution during extended storage, TMPP-AcSC6F5 bromide reacts with unprotected peptides through p-(dimethylamino)pyridine (DMAP)-promoted amidation in aqueous acetonitrile (15 min, ambient temperature) to form N-TMPP-Ac derivatives of peptides. These peptide derivatives are readily amenable to analysis by fast atom bombardment (FAB) and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. Greater than 90% conversion has been observed in transforming low-nanomole quantities of analyte using molar ratios of 1:5:10 (peptide/reagent/ DMAP). For reactions at the picomole level a slightly modified stoichiometry, with molar ratios of 1:10:500, is employed. Owing to the high reaction efficiency and the tolerance to moderate excess reagent and base during analysis by FAB- and MALDI-MS, the reaction mixture containing the modified peptides can be analyzed directly in most cases, without sample cleanup. Examples of the preparation and analysis of a variety of N-TMPP-acetyl-peptides (TMPP-Ac-peptides) ranging from hexamers to 15-mers are given. Collisionally activated dissociation tandem mass spectrometry of TMPP-Ac-derivatives showed dominant a-type ions, accompanied by d- and c-type ions in some cases, allowing sequence determination to be made in a straightforward manner.
DOI: 10.1021/ac9608578
PubMed: 8997893
Affiliations:
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Wu</name></author><author><name sortKey="Roth, K D" sort="Roth, K D" uniqKey="Roth K" first="K D" last="Roth">K D Roth</name></author><author><name sortKey="Yang, Y" sort="Yang, Y" uniqKey="Yang Y" first="Y" last="Yang">Y. 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Wu</name></author><author><name sortKey="Roth, K D" sort="Roth, K D" uniqKey="Roth K" first="K D" last="Roth">K D Roth</name></author><author><name sortKey="Yang, Y" sort="Yang, Y" uniqKey="Yang Y" first="Y" last="Yang">Y. Yang</name></author><author><name sortKey="Gage, D A" sort="Gage, D A" uniqKey="Gage D" first="D A" last="Gage">D A Gage</name></author><author><name sortKey="Watson, J T" sort="Watson, J T" uniqKey="Watson J" first="J T" last="Watson">J T Watson</name></author></analytic><series><title level="j">Analytical chemistry</title><idno type="ISSN">0003-2700</idno><imprint><date when="1997" type="published">1997</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Amino Acid Sequence</term><term>Indicators and Reagents</term><term>Mass Spectrometry</term><term>Molecular Sequence Data</term><term>Peptides (analysis)</term><term>Peptides (chemistry)</term><term>Sequence Analysis (methods)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Analyse de séquence ()</term><term>Données de séquences moléculaires</term><term>Indicateurs et réactifs</term><term>Peptides ()</term><term>Peptides (analyse)</term><term>Spectrométrie de masse</term><term>Séquence d'acides aminés</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analysis" xml:lang="en"><term>Peptides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Peptides</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Indicators and Reagents</term></keywords><keywords scheme="MESH" qualifier="analyse" xml:lang="fr"><term>Peptides</term></keywords><keywords scheme="MESH" qualifier="methods" xml:lang="en"><term>Sequence Analysis</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term><term>Mass Spectrometry</term><term>Molecular Sequence Data</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Analyse de séquence</term><term>Données de séquences moléculaires</term><term>Indicateurs et réactifs</term><term>Peptides</term><term>Spectrométrie de masse</term><term>Séquence d'acides aminés</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A highly activated ester containing a fixed positive charge, S-pentafluorophenyl [tris(2,4,6-trimethoxyphenyl)phosphonium]acetate bromide (TMPP-AcSC6F5 bromide), has been synthesized as a reagent for N-terminal modification of peptides. Stable in aqueous acetonitrile solution during extended storage, TMPP-AcSC6F5 bromide reacts with unprotected peptides through p-(dimethylamino)pyridine (DMAP)-promoted amidation in aqueous acetonitrile (15 min, ambient temperature) to form N-TMPP-Ac derivatives of peptides. These peptide derivatives are readily amenable to analysis by fast atom bombardment (FAB) and matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. Greater than 90% conversion has been observed in transforming low-nanomole quantities of analyte using molar ratios of 1:5:10 (peptide/reagent/ DMAP). For reactions at the picomole level a slightly modified stoichiometry, with molar ratios of 1:10:500, is employed. Owing to the high reaction efficiency and the tolerance to moderate excess reagent and base during analysis by FAB- and MALDI-MS, the reaction mixture containing the modified peptides can be analyzed directly in most cases, without sample cleanup. Examples of the preparation and analysis of a variety of N-TMPP-acetyl-peptides (TMPP-Ac-peptides) ranging from hexamers to 15-mers are given. Collisionally activated dissociation tandem mass spectrometry of TMPP-Ac-derivatives showed dominant a-type ions, accompanied by d- and c-type ions in some cases, allowing sequence determination to be made in a straightforward manner.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Michigan</li></region><settlement><li>East Lansing</li></settlement><orgName><li>Université d'État du Michigan</li></orgName></list><tree><noCountry><name sortKey="Gage, D A" sort="Gage, D A" uniqKey="Gage D" first="D A" last="Gage">D A Gage</name><name sortKey="Roth, K D" sort="Roth, K D" uniqKey="Roth K" first="K D" last="Roth">K D Roth</name><name sortKey="Watson, J T" sort="Watson, J T" uniqKey="Watson J" first="J T" last="Watson">J T Watson</name><name sortKey="Wu, J" sort="Wu, J" uniqKey="Wu J" first="J" last="Wu">J. Wu</name><name sortKey="Yang, Y" sort="Yang, Y" uniqKey="Yang Y" first="Y" last="Yang">Y. Yang</name></noCountry><country name="États-Unis"><region name="Michigan"><name sortKey="Huang, Z H" sort="Huang, Z H" uniqKey="Huang Z" first="Z H" last="Huang">Z H Huang</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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