Počet záznamů: 1
Nitrile Imines as Peptide and Oligonucleotide Photo-Cross-Linkers in Gas-Phase Ions
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SYSNO ASEP 0583028 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Nitrile Imines as Peptide and Oligonucleotide Photo-Cross-Linkers in Gas-Phase Ions Tvůrce(i) Wan, J. (US)
Nytka, M. (CZ)
Qian, H. (US)
Vu, K. (US)
Lemr, Karel (MBU-M) RID, ORCID
Tureček, F. (US)Zdroj.dok. Journal of the American Society for Mass Spectrometry. - : American Chemical Society - ISSN 1044-0305
Roč. 35, č. 2 (2024), s. 344-356Poč.str. 13 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova 1,3-dipolar cycloaddition ; noncovalent interactions ; molecular-dynamics ; bond formation ; linking ; dispersion ; complexes ; efficient ; charges ; binding Obor OECD Analytical chemistry Způsob publikování Omezený přístup Institucionální podpora MBU-M - RVO:61388971 UT WOS 001158685500001 EID SCOPUS 85184515839 DOI 10.1021/jasms.3c00379 Anotace Nitrile imines produced by photodissociation of 2,5-diaryltetrazoles undergo cross-linking reactions with amide groups in peptide-tetrazole (tet-peptide) conjugates and a tet-peptide-dinucleotide complex. Tetrazole photodissociation in gas-phase ions is efficient, achieving ca. 50% conversion with 2 laser pulses at 250 nm. The formation of cross-links was detected by CID-MS3 that showed structure-significant dissociations by loss of side-chain groups and internal peptide segments. The structure and composition of cross-linking products were established by a combination of UV-vis action spectroscopy and cyclic ion mobility mass spectrometry (c-IMS). The experimental absorption bands were found to match the bands calculated for vibronic absorption spectra of nitrile imines and cross-linked hydrazone isomers. The calculated collision cross sections (CCSth) for these ions were related to the matching experimental CCSexp from multipass c-IMS measurements. Loss of N-2 from tet-peptide conjugates was calculated to be a mildly endothermic reaction with Delta H-0 = 80 kJ mol(-1) in the gas phase. The excess energy in the photolytically formed nitrile imine is thought to drive endothermic proton transfer, followed by exothermic cyclization to a sterically accessible peptide amide group. The exothermic nitrile imine reaction with peptide amides is promoted by proton transfer and may involve an initial [3 + 2] cycloaddition followed by cleavage of the oxadiazole intermediate. Nucleophilic groups, such as cysteine thiol, did not compete with the amide cyclization. Nitrile imine cross-linking to 2 '-deoxycytidylguanosine was found to be >80% efficient and highly specific in targeting guanine. The further potential for exploring nitrile-imine cross-linking for biomolecular structure analysis is discussed. Pracoviště Mikrobiologický ústav Kontakt Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Rok sběru 2024 Elektronická adresa https://pubs.acs.org/doi/epdf/10.1021/jasms.3c00379
Počet záznamů: 1