Nitrile-Imine-Mediated Cross-Linking of Peptides to Oligonucleotides in Gas-Phase Ion Complexes

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F25%3A00637910" target="_blank" >RIV/61388963:_____/25:00637910 - isvavai.cz</a>

Alternative codes found

RIV/00216208:11310/25:10510108

Result on the web

<a href="https://doi.org/10.1021/jasms.5c00100" target="_blank" >https://doi.org/10.1021/jasms.5c00100</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jasms.5c00100" target="_blank" >10.1021/jasms.5c00100</a>

Result language

angličtina

Original language name

Nitrile-Imine-Mediated Cross-Linking of Peptides to Oligonucleotides in Gas-Phase Ion Complexes

Original language description

Gas-phase ion complexes of dinucleotides and trinucleotides with a diaryltetrazole-tagged peptide underwent covalent cross-linking upon UV photodissociation (UVPD) at 213 nm. The cross-linking reaction involved nitrile-imine intermediates produced by the loss of N-2 from the tetrazole, whereby cross-linking between the complex components competed with internal cross-linking within the peptide. The propensity for UVPD-induced cross-linking of DNA nucleobases was established for complexes of dinucleotides dAA, dCC, dGG, and dTT, that gave cross-link yields of 5%, 15%, 40%, and <1%, respectively. Analysis of UVPD-produced nitrile-imine intermediates by collision-induced dissociation (CID-MS3) gave cross-link yields of 71%, 75%, 94%, and 8% for dAA, dCC, dGG, and dTT, respectively. UVPD-CID-MS3 of isomeric trinucleotide-peptide complexes of dCGA, dAGC, dCAG, dACG, and dGCA showed nearly quantitative cross-linking that favored guanine regardless of its position in the sequence. Binding energies for the gas-phase ion complexes were obtained by Born-Oppenheimer molecular dynamics and density functional theory calculations at the M06-2X/def2qzvpp level. These calculations showed similar binding energies for the dAA, dCC, and dCAG complexes that were in the 195-221 kJ mol(-1) range, whereas binding to dGG and dTT was weaker. A mechanism for the novel cross-linking reaction between the nitrile imine and guanine was elucidated with a riboguanosine conjugate that was tagged with a diaryltetrazole group at 5 '-O. Product analysis as well as the calculated structures and energies suggested that cross-links resulted from an attack on the aromatic ring of an imine intermediate by the guanine carbonyl oxygen, followed by proton migrations.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

—

OECD FORD branch

10406 - Analytical chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2025

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Journal of the American Society for Mass Spectrometry

ISSN

1044-0305

e-ISSN

1879-1123

Volume of the periodical

36

Issue of the periodical within the volume

8

Country of publishing house

US - UNITED STATES

Number of pages

11

Pages from-to

1718-1728

UT code for WoS article

001517155600001

EID of the result in the Scopus database

2-s2.0-105009035281