Reactive trityl derivatives: stabilised carbocation mass-tags for life sciences applications
Identifieur interne : 000154 ( Main/Exploration ); précédent : 000153; suivant : 000155Reactive trityl derivatives: stabilised carbocation mass-tags for life sciences applications
Auteurs : Alexey V. Ustinov [Russie] ; Vadim V. Shmanai [Biélorussie] ; Kaajal Patel [Royaume-Uni] ; Irina A. Stepanova [Russie] ; Igor A. Prokhorenko [Russie] ; Irina V. Astakhova [Russie] ; Andrei D. Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa. [Russie] ; Mikhail V. Skorobogatyi [Russie] ; Pablo L. Bernad [Royaume-Uni] ; Safraz Khan [Royaume-Uni] ; Mona Shahgholi [États-Unis] ; Edwin M. Southern [Royaume-Uni] ; Vladimir A. Korshun [Russie] ; Mikhail S. Shchepinov [Royaume-Uni]Source :
- Organic & Biomolecular Chemistry [ 1477-0520 ] ; 2008.
Abstract
The rational design of novel triarylmethyl (trityl)-based mass tags (MT) for mass-spectrometric (MS) applications is described. We propose a pKR+ rule to correlate the stability of trityl carbocations with their MS performance: trityls with higher pKR+ values ionise and desorb better. Trityl blocks were synthesised that have high pKR+ values and are stable in conditions of MS analysis; these MTs can be ionised by matrix as well as irradiation with a 337 nm nitrogen laser. 13C-Labelled tags were prepared for MS quantitation applications. Moreover, the tags were equipped with a variety of functional groups allowing conjugation with different functionalities within (bio)molecules to enhance the MS characteristics of the latter. The MS behaviour of model polycationic trityl compounds with and without the matrix was studied to reveal that poly-trityl clusters are always singly charged under the (MA)LDI-TOF conditions. Several peptide-trityl conjugates were prepared and comparisons revealed a beneficial effect of trityl tags on the conjugate detection in MS. Trityl compounds containing para-methoxy- and dimethylamine groups, as well as a xanthene fragment, showed considerable enhancement in MS detection of model peptides; thus they are promising tools for proteomic applications. Dimethoxytrityl derivatives allow one to distinguish between Arg- and Lys-containing peptides. Maleimido trityl derivatives are suitable for the efficient derivatisation of thiol-containing peptides in pyridine.
Url:
DOI: 10.1039/b810600b
Affiliations:
- Biélorussie, Royaume-Uni, Russie, États-Unis
- Angleterre, District fédéral central, Oxfordshire
- Moscou, Oxford
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Korshun</name><affiliation wicri:level="3"><country xml:lang="fr">Russie</country><wicri:regionArea>Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, 117997, Miklukho-Maklaya 16/10, Moscow</wicri:regionArea><placeName><settlement type="city">Moscou</settlement><region>District fédéral central</region></placeName></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Russie</country></affiliation></author><author wicri:is="90%"><name sortKey="Shchepinov, Mikhail S" sort="Shchepinov, Mikhail S" uniqKey="Shchepinov M" first="Mikhail S." last="Shchepinov">Mikhail S. Shchepinov</name><affiliation wicri:level="3"><country xml:lang="fr">Royaume-Uni</country><wicri:regionArea>Tridend Technologies (a Division of OGT), Sandy Lane, Yarnton, OX5 1PF, Oxford</wicri:regionArea><placeName><settlement type="city">Oxford</settlement><region type="country">Angleterre</region><region type="comté" nuts="2">Oxfordshire</region></placeName></affiliation><affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j">Organic & Biomolecular Chemistry</title><title level="j" type="abbrev">Org. Biomol. Chem.</title><idno type="ISSN">1477-0520</idno><idno type="eISSN">1477-0539</idno><imprint><publisher>The Royal Society of Chemistry.</publisher><date type="published" when="2008">2008</date><biblScope unit="volume"></biblScope><biblScope unit="issue">24</biblScope><biblScope unit="page" from="4593">4593</biblScope><biblScope unit="page" to="4608">4608</biblScope></imprint><idno type="ISSN">1477-0520</idno></series><idno type="istex">6101E2B97B7639FA4CDCB4CC0D520CF5AEEF780C</idno><idno type="DOI">10.1039/b810600b</idno><idno type="ms-id">b810600b</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1477-0520</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract">The rational design of novel triarylmethyl (trityl)-based mass tags (MT) for mass-spectrometric (MS) applications is described. We propose a pKR+ rule to correlate the stability of trityl carbocations with their MS performance: trityls with higher pKR+ values ionise and desorb better. Trityl blocks were synthesised that have high pKR+ values and are stable in conditions of MS analysis; these MTs can be ionised by matrix as well as irradiation with a 337 nm nitrogen laser. 13C-Labelled tags were prepared for MS quantitation applications. Moreover, the tags were equipped with a variety of functional groups allowing conjugation with different functionalities within (bio)molecules to enhance the MS characteristics of the latter. The MS behaviour of model polycationic trityl compounds with and without the matrix was studied to reveal that poly-trityl clusters are always singly charged under the (MA)LDI-TOF conditions. Several peptide-trityl conjugates were prepared and comparisons revealed a beneficial effect of trityl tags on the conjugate detection in MS. Trityl compounds containing para-methoxy- and dimethylamine groups, as well as a xanthene fragment, showed considerable enhancement in MS detection of model peptides; thus they are promising tools for proteomic applications. Dimethoxytrityl derivatives allow one to distinguish between Arg- and Lys-containing peptides. Maleimido trityl derivatives are suitable for the efficient derivatisation of thiol-containing peptides in pyridine.</div></front></TEI><affiliations><list><country><li>Biélorussie</li><li>Royaume-Uni</li><li>Russie</li><li>États-Unis</li></country><region><li>Angleterre</li><li>District fédéral central</li><li>Oxfordshire</li></region><settlement><li>Moscou</li><li>Oxford</li></settlement></list><tree><country name="Russie"><region name="District fédéral central"><name sortKey="Ustinov, Alexey V" sort="Ustinov, Alexey V" uniqKey="Ustinov A" first="Alexey V." last="Ustinov">Alexey V. 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Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa.</name><name sortKey="Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa, Andrei D" sort="Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa, Andrei D" uniqKey="Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa A" first="Andrei D." last="Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa.">Andrei D. Malakhovpresent Address Department Of Chemistry Texas A Amp M University College Station Tx Usa.</name><name sortKey="Prokhorenko, Igor A" sort="Prokhorenko, Igor A" uniqKey="Prokhorenko I" first="Igor A." last="Prokhorenko">Igor A. Prokhorenko</name><name sortKey="Prokhorenko, Igor A" sort="Prokhorenko, Igor A" uniqKey="Prokhorenko I" first="Igor A." last="Prokhorenko">Igor A. Prokhorenko</name><name sortKey="Skorobogatyi, Mikhail V" sort="Skorobogatyi, Mikhail V" uniqKey="Skorobogatyi M" first="Mikhail V." last="Skorobogatyi">Mikhail V. Skorobogatyi</name><name sortKey="Skorobogatyi, Mikhail V" sort="Skorobogatyi, Mikhail V" uniqKey="Skorobogatyi M" first="Mikhail V." last="Skorobogatyi">Mikhail V. Skorobogatyi</name><name sortKey="Stepanova, Irina A" sort="Stepanova, Irina A" uniqKey="Stepanova I" first="Irina A." last="Stepanova">Irina A. Stepanova</name><name sortKey="Stepanova, Irina A" sort="Stepanova, Irina A" uniqKey="Stepanova I" first="Irina A." last="Stepanova">Irina A. Stepanova</name><name sortKey="Ustinov, Alexey V" sort="Ustinov, Alexey V" uniqKey="Ustinov A" first="Alexey V." last="Ustinov">Alexey V. Ustinov</name></country><country name="Biélorussie"><noRegion><name sortKey="Shmanai, Vadim V" sort="Shmanai, Vadim V" uniqKey="Shmanai V" first="Vadim V." last="Shmanai">Vadim V. 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Southern</name></country><country name="États-Unis"><noRegion><name sortKey="Shahgholi, Mona" sort="Shahgholi, Mona" uniqKey="Shahgholi M" first="Mona" last="Shahgholi">Mona Shahgholi</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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