2007
DOI: 10.1002/ejic.200601091
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Ten Years of a Biomimetic Approach to the Copper(II) Radical Site of Galactose Oxidase

Abstract: An overview of recent progress in the modeling of the copper(II)‐phenoxyl entity of the metalloenzyme Galactose Oxidase (GO) is presented. GO is an enzyme that is extremely engineered by nature: its active site exhibits several unusual features, such as a coordinated tyrosyl radical, post‐translationally modified amino acids, and π‐stacked residues. Understanding each of these particularities has posed a challenge for chemists, who have consequently developed several biomimetic complexes during the last decade… Show more

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Cited by 192 publications
(130 citation statements)
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References 106 publications
(225 reference statements)
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“…12,[17][18][19][20][21][22][23][24][25][26]. The para positioning of sulfanyl substituents in 1 R2 is designed purposefully to assure minimal copper coordination changes by preserving the sterically abutting ortho-t-butyl substituents (R 3 , Fig.…”
mentioning
confidence: 99%
“…12,[17][18][19][20][21][22][23][24][25][26]. The para positioning of sulfanyl substituents in 1 R2 is designed purposefully to assure minimal copper coordination changes by preserving the sterically abutting ortho-t-butyl substituents (R 3 , Fig.…”
mentioning
confidence: 99%
“…Such a trend is also applied to the salen-type complexes, and most of the Cu(II) and group 10 metal(II) salen-type complexes exhibited two reversible redox waves in the range of 0 to 1.5 V vs NHE, due to having two phenolate moieties [29][30][31][39][40][41][42][43][44][45][46][47]. On the other hand, the metal centered one-and two-electron oxidized complexes may possibly be generated in the similar potential range.…”
Section: Scheme 1 Proposed Mechanism Of Galactose Oxidase (Go)mentioning
confidence: 92%
“…For understanding the detailed mechanism of GO and the properties of the metal complexes with the coordinated phenoxyl radical, many metal−phenolate complexes have been synthesized, and their oxidation behavior and properties of the oxidized forms have been characterized in [12,13,[29][30][31][32][33][34][35][36]. Salen (Salen = di(salicylidene)ethylenediamine) and its family are one of the most important and famous ligands having two phenol moieties (Figure 3) [37,38].…”
Section: Scheme 1 Proposed Mechanism Of Galactose Oxidase (Go)mentioning
confidence: 99%
See 1 more Smart Citation
“…The related enzyme glyoxal oxidase, which catalyzes the oxidation of aldehydes to carboxylic acids, has a similar reactivity and active site composition (Chaudhuri & Wieghardt, 2001). Modeling the Cu(II)-phenoxo state (GOase OX ) in order to improve our understanding of the mechanistic details of the first rate-determining step of the catalytic cycle has been a challenge for biomimetic chemists (Wang et al, 1998;Thomas, 2007). Chelate effect, sulfur involvement and steric shielding have been employed to mimic the stability of the Cu(II)-phenoxo moiety.…”
Section: Copper Biomimetic Systemsmentioning
confidence: 99%