Literature DB >> 33356198

Temperature-Dependent Reactivity of a Non-heme FeIII(OH)(SR) Complex: Relevance to Isopenicillin N Synthase.

Vishal Yadav1, Maxime A Siegler1, David P Goldberg1.   

Abstract

Non-heme iron complexes with cis-FeIII(OH)(SAr/OAr) coordination were isolated and examined for their reactivity with a tertiary carbon radical. The sulfur-ligated complex shows a temperature dependence on •OH versus ArS• transfer, whereas the oxygen-ligated complex does not. These results provide the first working model for C-S bond formation in isopenicillin N synthase and indicate that kinetic control may be a key factor in the selectivity of non-heme iron "rebound" processes.

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Year:  2020        PMID： 33356198      PMCID： PMC8130865          DOI： 10.1021/jacs.0c09688

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  57 in total

1.  Structural and spectroscopic features of a cis (hydroxo)-Fe(III)-(carboxylato) configuration as an active site model for lipoxygenases.

Authors:  Seiji Ogo; Ryo Yamahara; Mark Roach; Tomoyoshi Suenobu; Michihiko Aki; Takashi Ogura; Teizo Kitagawa; Hideki Masuda; Shunichi Fukuzumi; Yoshihito Watanabe
Journal:  Inorg Chem       Date:  2002-10-21       Impact factor: 5.165

2.  Structure of isopenicillin N synthase complexed with substrate and the mechanism of penicillin formation.

Authors:  P L Roach; I J Clifton; C M Hensgens; N Shibata; C J Schofield; J Hajdu; J E Baldwin
Journal:  Nature       Date:  1997-06-19       Impact factor: 49.962

3.  A synthetic analogue of the active site of Fe-containing nitrile hydratase with carboxamido N and thiolato S as donors: synthesis, structure, and reactivities.

Authors:  J C Noveron; M M Olmstead; P K Mascharak
Journal:  J Am Chem Soc       Date:  2001-04-11       Impact factor: 15.419

4.  Dioxygen-Derived Nonheme Mononuclear FeIII(OH) Complex and Its Reactivity with Carbon Radicals.

Authors:  Vishal Yadav; Jesse B Gordon; Maxime A Siegler; David P Goldberg
Journal:  J Am Chem Soc       Date:  2019-06-20       Impact factor: 15.419

5.  Spectroscopic Evidence for the Two C-H-Cleaving Intermediates of Aspergillus nidulans Isopenicillin N Synthase.

Authors:  Esta Tamanaha; Bo Zhang; Yisong Guo; Wei-Chen Chang; Eric W Barr; Gang Xing; Jennifer St Clair; Shengfa Ye; Frank Neese; J Martin Bollinger; Carsten Krebs
Journal:  J Am Chem Soc       Date:  2016-07-05       Impact factor: 15.419

6.  Transition-metal mediated carbon-sulfur bond activation and transformations.

Authors:  Liandi Wang; Wei He; Zhengkun Yu
Journal:  Chem Soc Rev       Date:  2013-01-21       Impact factor: 54.564

7.  The mechanism for isopenicillin N synthase from density-functional modeling highlights the similarities with other enzymes in the 2-His-1-carboxylate family.

Authors:  Marcus Lundberg; Per E M Siegbahn; Keiji Morokuma
Journal:  Biochemistry       Date:  2007-12-29       Impact factor: 3.162

8.  A hydrogen-bond facilitated cycle for oxygen reduction by an acid- and base-compatible iron platform.

Authors:  Han Sen Soo; Alexis C Komor; Anthony T Iavarone; Christopher J Chang
Journal:  Inorg Chem       Date:  2009-11-02       Impact factor: 5.165

9.  Interactions of isopenicillin N synthase with cyclopropyl-containing substrate analogues reveal new mechanistic insight.

Authors:  Annaleise R Howard-Jones; Jonathan M Elkins; Ian J Clifton; Peter L Roach; Robert M Adlington; Jack E Baldwin; Peter J Rutledge
Journal:  Biochemistry       Date:  2007-03-31       Impact factor: 3.162

10.  Does Substrate Positioning Affect the Selectivity and Reactivity in the Hectochlorin Biosynthesis Halogenase?

Authors:  Amy Timmins; Nicholas J Fowler; Jim Warwicker; Grit D Straganz; Sam P de Visser
Journal:  Front Chem       Date:  2018-10-30       Impact factor: 5.221
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