Structural models for the reduced form of vanadate-dependent peroxidases: vanadyl complexes with bidentate chiral Schiff base ligands

Santoni, Gabriella; Rehder, Dieter

doi:10.1016/j.jinorgbio.2003.10.020

Cited by 34 publications

(14 citation statements)

References 28 publications

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“…However, some differences in the molecular conformation were found which reflected the opposite configuration on C1. The structure of S-enantiomer reported here was similar to that of S-enantiomer of the chloro-analog 24 , for which the two torsion angles described above are 120.7 and 48.2°.…”

Section: Resultssupporting

confidence: 71%

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

Jaworska¹,

Wełniak²,

Zięciak³

et al. 2011

Arkivoc

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A group of bidentate Schiff bases derived from enantiomerically pure (S)--methylbenzylamine was synthesized. Crystal structure was determined for three compounds. Schiff bases were used as chiral ligands in the asymmetric addition of Et2Zn to aldehydes. The obtained enantioselectivity was e.e.=8-94% depending on the substrate and the best was observed for (S,E)-2-(1-(1-phenylethylimino)-ethyl)phenol. The enantioselectivity increase was connected with the substituent-induced electronic effects in the substrate molecules. Molecular modeling resulted in the models of the 3D structures of Zn-Zn complex catalysts containing investigated Schiff bases, which were consistent with the reported chirality of the addition product and explained observed e.e. The presented transition state models allow explaining the change of the absolute configuration of diethylzinc addition product in the case of using ortho-substituted aldehydes.

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Section: Resultssupporting

confidence: 71%

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

Jaworska¹,

Wełniak²,

Zięciak³

et al. 2011

Arkivoc

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“…The crystal structure of (I) is isomorphous with that of the Cl derivative (Santoni & Rehder, 2004), although the reported structure is of the S enantiomer. The molecule of (I) ( Fig.…”

Section: Commentmentioning

confidence: 95%

A chiral photochromic Schiff base: (R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol

Akitsu

Einaga

2006

Acta Cryst E

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“…However, the pentacoordinate arrangement in the presence of bulky groups can undergo a trigonal bipyramidal distortion, which may influence the enzymatic and/or biological activity of V proteins. For example, a trigonal bipyramidal distortion has been proposed by Santoni and Rehder for the reduced form of bromoperoxidase from the marine brown alga Ascophyllum nodosum 6. Therefore, to correctly study these systems in the absence of single‐crystal X‐ray diffraction analysis, it is fundamental to have a tool to characterize the geometry of a V IV O 2+ species and its eventual distortion.…”

Section: Introductionmentioning

confidence: 99%

The Effect of Trigonal Bipyramidal Distortion of Pentacoordinate V^IVO²⁺ Species on their Structural, Electronic and Spectroscopic Parameters

Micera

Garribba

2011

Eur J Inorg Chem

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The effect of trigonal bipyramidal distortion of pentacoordinate V IV O 2+ species on their structural, electronic and spectroscopic parameters was calculated by DFT methods. In particular i) the bis chelated species with [VO(LH -1 ) 2 ]2-stoichiometry formed in water with five α-hydroxycarboxylic acid ligands [glycolic (glycH), lactic (lactH), 2-hydroxyisobutyric (2-hibH), 2-ethyl-2-hydroxybutyric (2-ehbH) and 2-isopropyl-2-hydroxybutyric (2-iPrhbH) acids], ii) the bis complexes [VOL 2 ] formed in the solid state with three salicylaldimine derivatives [N-methylsalicylaldimine (MeSalH), N-isopropylo-methylsalicylaldimine (iPr-MeSalH) and N-methyl-o-tertbutyl-p-methylsalicylaldimine (tBu-MeSalH)] and iii) the solid bis chelated compounds with composition [VOL 2 ] formed

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Structural models for the reduced form of vanadate-dependent peroxidases: vanadyl complexes with bidentate chiral Schiff base ligands

Cited by 34 publications

References 28 publications

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

A chiral photochromic Schiff base: (R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol

The Effect of Trigonal Bipyramidal Distortion of Pentacoordinate V^IVO²⁺ Species on their Structural, Electronic and Spectroscopic Parameters

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Structural models for the reduced form of vanadate-dependent peroxidases: vanadyl complexes with bidentate chiral Schiff base ligands

Cited by 34 publications

References 28 publications

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

Bidentate Schiff bases derived from (S)-α-methylbenzylamine as chiral ligands in the electronically controlled asymmetric addition of diethylzinc to aldehydes

A chiral photochromic Schiff base: (R)-4-bromo-2-[(1-phenylethyl)iminomethyl]phenol

The Effect of Trigonal Bipyramidal Distortion of Pentacoordinate VIVO2+ Species on their Structural, Electronic and Spectroscopic Parameters

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The Effect of Trigonal Bipyramidal Distortion of Pentacoordinate V^IVO²⁺ Species on their Structural, Electronic and Spectroscopic Parameters