Počet záznamů: 1  

Nitrile Imines as Peptide and Oligonucleotide Photo-Cross-Linkers in Gas-Phase Ions

  1. 1.
    SYSNO ASEP0583028
    Druh ASEPJ - Článek v odborném periodiku
    Zařazení RIVJ - Článek v odborném periodiku
    Poddruh JČlánek ve WOS
    NázevNitrile 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. 344-356
    Poč.str.13 s.
    Jazyk dok.eng - angličtina
    Země vyd.US - Spojené státy americké
    Klíč. slova1,3-dipolar cycloaddition ; noncovalent interactions ; molecular-dynamics ; bond formation ; linking ; dispersion ; complexes ; efficient ; charges ; binding
    Obor OECDAnalytical chemistry
    Způsob publikováníOmezený přístup
    Institucionální podporaMBU-M - RVO:61388971
    UT WOS001158685500001
    EID SCOPUS85184515839
    DOI10.1021/jasms.3c00379
    AnotaceNitrile 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.
    PracovištěMikrobiologický ústav
    KontaktEliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231
    Rok sběru2024
    Elektronická adresahttps://pubs.acs.org/doi/epdf/10.1021/jasms.3c00379
Počet záznamů: 1  

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