Differential Effects of the Zn-His-Bkb vs Zn-His-[Asp/Glu] Triad on Zn-Core Stability and Reactivity.

The most common partner of the Zn-bound His is the Asp/Glu carboxylate side chain in catalytic Zn sites and the backbone (Bkb) carbonyl group in structural Zn sites. To elucidate the factors governing the selection of the second-shell partner of the Zn-bound His in structural/catalytic Zn sites, sys...

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Published in:Journal of the American Chemical Society Vol. 127; no. 32; pp. 11336 - 11348
Main Authors: Yen-lin Lin, Yu-ming Lee, Carmay Lim
Format: Article
Published: American Chemical Society 8/17/2005
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Online Access:View this record in EBSCOhost
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      dt: 8/17/2005
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        10.1021/ja051304u
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      tig:
        atl: Differential Effects of the Zn-His-Bkb vs Zn-His-[Asp/Glu] Triad on Zn-Core Stability and Reactivity.
      aug:
        au:
          Yen-lin Lin
          Yu-ming Lee
          Carmay Lim
        affil:
          Institute of Biomedical Sciences, Academia Sinica, Taipei 115, Taiwan R.O.C.
          Department of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan R.O.C.
      su:
        Zinc
        Particles (Nuclear physics)
        Density functionals
        Chemical reactions
        Research
        Fluids
      sug:
        subj:
          Zinc
          Particles (Nuclear physics)
          Density functionals
          Chemical reactions
          Research
          Fluids
      ab: The most common partner of the Zn-bound His is the Asp/Glu carboxylate side chain in catalytic Zn sites and the backbone (Bkb) carbonyl group in structural Zn sites. To elucidate the factors governing the selection of the second-shell partner of the Zn-bound His in structural/catalytic Zn sites, systematic studies using density functional theory and continuum dielectric calculations were performed to determine the relative contributions of the second-shell Bkb carbonyl and the Asp/Glu carboxylate to the Zn-core stability and reactivity. The results show that the contributions of the second-shell Bkb carbonyl and Asp/ Glu carboxylate to the Zn-core stability depend mainly on the solvent accessibility of the Zn-site and the composition of the Zn-core. They reveal the advantage of a second-shell Bkb carbonyl in anionic Zn cavities: it stabilizes anionic, buried Zn-cores more than the corresponding negatively charged Asp/Glu carboxylate, thus explaining the absence of the Zn-His-Asp/Glu triad in structural [Zn(Cys)(His)] cores. They also reveal the advantage of a second-shell Asp/Glu carboxylate in catalytic Zn-cores: relative to a Bkb carbonyl group, it increases (i) the HOMO energy of the cationic/neutral zinc core, (ii) the reactivity of the attacking Zn-bound OH, (iii) electron transfer to the substrate, and (iv) the stability of the metal complex upon electron transfer. Furthermore, a second-shell Asp/Glu carboxylate could facilitate product release in the common cationic catalytic cores, by acting as a proton acceptor of the Zn-bound His creating an Asp┅His dyad that stabilizes the zinc dication more than the respective Bkb┅His° dyad.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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