Articles producció científica> Química Analítica i Química Orgànica

Binding of Acetylated Lysine by Using a Water Soluble Aryl Extended Calix[4]pyrrole

  • Identification data

    Identifier: imarina:9363282
  • Authors:

    Orlandini M
    Pedrini A
    Marchetti D
    Li Y
    Aragay G
    Dalcanale E
    Ballester P
    Pinalli R
  • Others:

    Author, as appears in the article.: Orlandini M; Pedrini A; Marchetti D; Li Y; Aragay G; Dalcanale E; Ballester P; Pinalli R
    Department: Química Analítica i Química Orgànica
    URV's Author/s: Li, Yifan
    Keywords: Tetra-aryl-extended calix[4]pyrrole Solvation/desolvation effects Selectivity Post translational modifications Peptides Molecular recognition Methylation Complexation Acetyl lysine
    Abstract: Post-translational modifications of lysine in histones, as methylation and acetylation, have well established functions in epigenetics and are emerging as important actors in broader biological regulation. Currently, the detection of acetylated lysine (Kac) in water solution as free amino acid or protein residue remains challenging. Acetylated lysine is a neutral amino acid, and the lack of ion-dipole interactions causes the decrease in binding affinity displayed by synthetic molecular receptors with respect to the other lysine modifications. Here, we report molecular modeling calculations and 1H NMR experiments to investigate the binding properties of two different calix[4]pyrrole receptors towards Kac. Computational analyses reveal that tetra-aryl-extended calix[4]pyrrole (1) preferentially binds the cis-Kac conformer over the trans one due to steric considerations and more favorable interactions. Experimental 1H NMR titration experiments confirm the formation of a 1 : 1 complex between receptor 1 and cis-Kac, with a Ka exceeding 103 M-1. Conversely, the super-aryl-extended calix[4]pyrrole 2 is less efficient in binding Kac, due to unfavorable solvation/desolvation effects, as proven by 1H NMR experiments. Moreover, receptor 1 showed a higher affinity for Kac over other lysine modifications, such as methylated lysines.The selective molecular recognition properties of two different calix[4]pyrrole receptors toward the cis isomer of acetylated lysine (cis-Kac) are investigated. The formation of a 1 : 1 complex is favoured for the aryl-extended receptor compared to the superaryl-extended featuring a deeper cavity for which the energetically not favourable desolvation of the aminoacidic group hampers the guest inclusion in the hydrophobic cavity. image
    Thematic Areas: Química Organic chemistry Medicina i Materiais Interdisciplinar General medicine General chemistry Farmacia Engenharias iii Engenharias ii Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Chemistry Catalysis Biotecnología Biodiversidade Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: yifan.li@estudiants.urv.cat
    Author identifier: 0000-0001-8708-0004
    Record's date: 2024-07-20
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/chem.202303715
    Licence document URL: http://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Chemistry-A European Journal. 30 (18): e202303715-e202303715
    APA: Orlandini M; Pedrini A; Marchetti D; Li Y; Aragay G; Dalcanale E; Ballester P; Pinalli R (2024). Binding of Acetylated Lysine by Using a Water Soluble Aryl Extended Calix[4]pyrrole. Chemistry-A European Journal, 30(18), e202303715-e202303715. DOI: 10.1002/chem.202303715
    Article's DOI: 10.1002/chem.202303715
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2024
    Publication Type: Journal Publications
  • Keywords:

    Catalysis,Chemistry,Chemistry (Miscellaneous),Chemistry, Multidisciplinary,Organic Chemistry
    Tetra-aryl-extended calix[4]pyrrole
    Solvation/desolvation effects
    Selectivity
    Post translational modifications
    Peptides
    Molecular recognition
    Methylation
    Complexation
    Acetyl lysine
    Química
    Organic chemistry
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias iii
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Chemistry
    Catalysis
    Biotecnología
    Biodiversidade
    Astronomia / física
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