7 publications

7 publications

Albumin-Conjugated Corrole Metal Complexes: Extremely Simple Yet Very Efficient Biomimetic Oxidation Systems

Gross, Z.

J. Am. Chem. Soc. 2005, 127, 2883-2887, 10.1021/ja045372c

An extremely simple biomimetic oxidation system, consisting of mixing metal complexes of amphiphilic corroles with serum albumins, utilizes hydrogen peroxide for asymmetric sulfoxidation in up to 74% ee. The albumin-conjugated manganese corroles also display catalase-like activity, and mechanistic evidence points toward oxidant-coordinated manganese(III) as the prime reaction intermediate.


Metal: Mn
Ligand type: Corrole
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Sulfoxidation
Max TON: 8
ee: 74
PDB: ---
Notes: ---

Metal: Mn
Ligand type: Corrole
Anchoring strategy: Supramolecular
Optimization: Chemical & genetic
Reaction: Sulfoxidation
Max TON: 42
ee: 52
PDB: ---
Notes: ---

Asymmetric Catalytic Sulfoxidation by a Novel VIV8 Cluster Catalyst in the Presence of Serum Albumin: A Simple and Green Oxidation System

Bian, H.-D.; Huang, F.-P.

RSC Adv. 2016, 6, 44154-44162, 10.1039/C6RA08153C

Enantioselective oxidation of a series of alkyl aryl sulfides catalyzed by a novel VIV8 cluster is tested in an aqueous medium in the presence of serum albumin. The procedure is simple, environmentally friendly, selective, and highly reactive.


Metal: V
Anchoring strategy: Undefined
Optimization: Chemical
Reaction: Sulfoxidation
Max TON: 140
ee: 77
PDB: ---
Notes: Screening with different serum albumins.

Bovine Serum Albumin-Cobalt(II) Schiff Base Complex Hybrid: An Efficient Artificial Metalloenzyme for Enantioselective Sulfoxidation using Hydrogen Peroxide

Bian, H.-D.; Liang, H.

Dalton Trans. 2016, 45, 8061-8072, 10.1039/C5DT04507J

An artificial metalloenzyme (BSA–CoL) based on the incorporation of a cobalt(ii) Schiff base complex {CoL, H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol} with bovine serum albumin (BSA) has been synthesized and characterized.


Metal: Co
Ligand type: Amine; Phenolate
Anchoring strategy: Supramolecular
Optimization: Chemical
Reaction: Sulfoxidation
Max TON: 98
ee: 87
PDB: ---
Notes: ---

Copper–Phthalocyanine Conjugates of Serum Albumins as Enantioselective Catalysts in Diels–Alder Reactions

Reetz, M.T.

Angew. Chem. Int. Ed. 2006, 45, 2416-2419, 10.1002/anie.200504561

Chirality from blood: Serum albumins form strong complexes with CuII–phthalocyanines, leading to protein conjugates. These hybrid catalysts promote enantioselective Diels–Alder reactions, such as that of azachalcones 1 with cyclopentadiene (2) to give products 3 with 85–98 % ee.


Metal: Cu
Ligand type: Phthalocyanine
Anchoring strategy: Supramolecular
Optimization: Chemical
Max TON: 45.5
ee: 98
PDB: ---
Notes: Chirality from blood: Serum albumins form strong complexes with CuII–phthalocyanines, leading to protein conjugates. These hybrid catalysts promote enantioselective Diels–Alder reactions, such as that of azachalcones 1 with cyclopentadiene (2) to give products 3 with 85–98 % ee.

Oxidation Catalysis via Visible-Light Water Activation of a [Ru(bpy)3]2+ Chromophore BSA–Metallocorrole Couple

Gross, Z.; Mahy, J.-P.

Dalton Trans. 2016, 45, 706-710, 10.1039/c5dt04158a

Light induced enantioselective oxidation of an organic molecule with water as the oxygen atom source is demonstrated in a system where chirality is induced by a protein, oxygen atom transfer by a manganese corrole, and photocatalysis by ruthenium complexes.


Metal: Mn
Ligand type: Corrole
Anchoring strategy: Supramolecular
Optimization: ---
Reaction: Sulfoxidation
Max TON: 21
ee: 16
PDB: ---
Notes: Water as oxygen source

Stereoselective Sulfoxidation Catalyzed by Achiral Schiff Base Complexes in the Presence of Serum Albumin in Aqueous Media

Bian, H.-D.; Huang, F.-P.

Tetrahedron: Asymmetry 2017, 28, 1700-1707, 10.1016/j.tetasy.2017.10.021

Four coordination complexes ML derived from an achiral Schiff base ligand (H2L = 2,2′-[(1,2-ethanediyl)bis(nitrilopropylidyne)]bisphenol) have been synthesized and characterized. A method is described for the enantioselective oxidation of a series of aryl alkyl sulfides using the coordination complexes in the presence of serum albumins (SAs) in an aqueous medium at ambient temperature. The mixture of metal complexes with serum albumins is useful for inducing asymmetric catalysis. The complex, albumin source and substrate influence stereoselective sulfoxidation. At optimal pH with the appropriate oxidant, some of ML/SA systems are identified as very efficient catalysts, giving the corresponding sulfoxides in excellent chemical yield (up to 100%) and good enantioselectivity (up to 94% ee) in certain cases. UV–visible spectroscopic data provide evidence that stronger binding between the complex and serum albumin lead to higher enantioselectivity.


Metal: Co
Anchoring strategy: Undefined
Optimization: ---
Reaction: Sulfoxidation
Max TON: ~60
ee: 59
PDB: ---
Notes: ---

The Bovine Serum Albumin-2-Phenylpropane-1,2-diolatodioxoosmium(VI) Complex as an Enantioselective Catalyst for cis-Hydroxylation of Alkenes

Kokubo, T.; Okano, M.

J. Chem. Soc., Chem. Commun. 1983, 0, 769-770, 10.1039/C39830000769

The 1:1 complex between an osmate ester and bovine serum albumin was found to be effective as an enantioselective catalyst in the cis-hydroxylation of alkenes, affording diols in up to 68% e.e. and turnover of the catalyst with t-butyl hydroperoxide.


Metal: Os
Ligand type: Undefined
Anchoring strategy: Undefined
Optimization: ---
Reaction: Dihydroxylation
Max TON: 40
ee: 68
PDB: ---
Notes: ---