Charge Relay Without Proton Transfer: Coupling of Two Short Hydrogen Bonds via Imidazole in Models of Catalytic Triad of Serine Protease Active Site

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Charge Relay Without Proton Transfer: Coupling of Two Short Hydrogen Bonds via Imidazole in Models of Catalytic Triad of Serine Protease Active Site. / Тупикина, Елена Юрьевна; Сигалов, М.; Алкхудер, Омар ; Толстой, Петр Михайлович.

In: ChemPhysChem, 29.04.2024.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{f3f9a965b7aa4bee85bfc6985852cae8,

title = "Charge Relay Without Proton Transfer: Coupling of Two Short Hydrogen Bonds via Imidazole in Models of Catalytic Triad of Serine Protease Active Site",

abstract = "A homologous series of 20 substituted alcohol‐imidazole‐acetate model complexes imitating the charge relay system in Ser‐His‐Asp catalytic triad of serine proteases is considered quantum‐chemically. We show qualitatively that the geometries of alcohol‐imidazole and imidazole‐acetate short hydrogen bonds are strongly coupled via the central imidazole and such complexes are capable of effectively relaying the charge from acetate to alcohol moiety upon relatively small concerted proton displacements. We hypothesize an alternative catalytic mechanism of serine proteases that does not require two complete proton transfers or hydrogen bond breakage between Ser and His residues.",

author = "Тупикина, {Елена Юрьевна} and М. Сигалов and Омар Алкхудер and Толстой, {Петр Михайлович}",

year = "2024",

month = apr,

day = "29",

doi = "10.1002/cphc.202300970",

language = "English",

journal = "Chemphyschem : a European journal of chemical physics and physical chemistry",

issn = "1439-4235",

publisher = "Wiley-Blackwell",

}

RIS

TY - JOUR

T1 - Charge Relay Without Proton Transfer: Coupling of Two Short Hydrogen Bonds via Imidazole in Models of Catalytic Triad of Serine Protease Active Site

AU - Тупикина, Елена Юрьевна

AU - Сигалов, М.

AU - Алкхудер, Омар

AU - Толстой, Петр Михайлович

PY - 2024/4/29

Y1 - 2024/4/29

N2 - A homologous series of 20 substituted alcohol‐imidazole‐acetate model complexes imitating the charge relay system in Ser‐His‐Asp catalytic triad of serine proteases is considered quantum‐chemically. We show qualitatively that the geometries of alcohol‐imidazole and imidazole‐acetate short hydrogen bonds are strongly coupled via the central imidazole and such complexes are capable of effectively relaying the charge from acetate to alcohol moiety upon relatively small concerted proton displacements. We hypothesize an alternative catalytic mechanism of serine proteases that does not require two complete proton transfers or hydrogen bond breakage between Ser and His residues.

AB - A homologous series of 20 substituted alcohol‐imidazole‐acetate model complexes imitating the charge relay system in Ser‐His‐Asp catalytic triad of serine proteases is considered quantum‐chemically. We show qualitatively that the geometries of alcohol‐imidazole and imidazole‐acetate short hydrogen bonds are strongly coupled via the central imidazole and such complexes are capable of effectively relaying the charge from acetate to alcohol moiety upon relatively small concerted proton displacements. We hypothesize an alternative catalytic mechanism of serine proteases that does not require two complete proton transfers or hydrogen bond breakage between Ser and His residues.

UR - https://www.mendeley.com/catalogue/4d261288-8995-30b9-a173-38e80a9804b1/

U2 - 10.1002/cphc.202300970

DO - 10.1002/cphc.202300970

M3 - Article

JO - Chemphyschem : a European journal of chemical physics and physical chemistry

JF - Chemphyschem : a European journal of chemical physics and physical chemistry

SN - 1439-4235

M1 - e202300970

ER -

ID: 119571428