Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen

Ouchi, Akihiko; Zandomeneghi, Giorgia; Zandomeneghi, Maurizio

doi:10.1002/chir.10026

Cited by 34 publications

(46 citation statements)

References 28 publications

(6 reference statements)

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“…Another control experiment used bovine serum albumin (BSA) (Mw 66 kDa). In this case, BSA and racemic BN were mixed in a one‐to‐one ratio because it was assumed that one BN molecule is bound per BSA molecule from a study on the complexation of BINOL with BSA . Although one enantiomer ( R ‐isomer) is eluted preferentially, the e.e .…”

Section: Figuresupporting

confidence: 69%

Direct Chiral Separation of Binaphthyl Derivatives Using Atroposelective Antibodies

et al. 2017

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A simple procedure for chiral separation based on the difference in the molecular weights of the antigen-antibody complex and analyte is developed. We raise monoclonal antibodies (mAbs) highly specific for the R-or S-isomer of a binaphthyl derivative (BN) by immunizing mice with the corresponding BN enantiomer. Aqueous solutions of racemic BN are mixed with mAbs. The free BN is separated by ultrafiltration. The enantiomers of BN are obtained with a high e.e. using atroposelective antibodies.Chirality is crucial in various scientific fields such as pharmaceuticals, [1] chemistry, [2][3][4] and materials science. [5] For example, in pharmaceutical applications employing a specific enantiomer is especially important. Often one enantiomer displays the desired effect, while the other elicits serious side effects. Therefore, chiral separations on both industrial and laboratory scales are important. High-performance liquid chromatography is a popular chiral separation methodology. [6] To date, many researchers have devoted much effort to develop chiral stationary phases (CSPs) such as synthetic polymers, [7] saccharides, [8,9] biomacromolecules, etc. [10][11][12] However, trial and error is still required for developing CSPs. One promising approach toward a straightforward chiral separation strategy is to use antibodies that precisely recognize the chirality of the target molecule. [13] With the advent of cell technology, [14] it is now possible to prepare individual antibodies, monoclonal antibodies (mAbs), in large amounts and in a homogeneous form semi-permanently.Many researchers have developed mAbs against optically active compounds for various purposes. [15][16][17][18][19][20] Among them, the use of mAbs as CSP of immuno affinity chiral columns has been extensively studied. [21] However, harsh elution conditions are necessary due to the high affinity of mAbs against target molecules. Eluting a tightly bound enantiomer while maintaining the stability of mAbs is problematic. [22][23][24] In addition, optimization of the immobilization method of mAbs onto columns is necessary to retain the binding affinity of mAbs. [25] To fully utilize the characteristic of mAbs, a more convenient methodology without columns for chiral separation is necessary.Our research focuses on the basic properties of mAbs, including high specificity for the target molecule and the molecular weight. Unlike chromatographic methods, the high molecular recognition ability of mAb can separate enantiomers with a one-step physical event. The large difference in the molecular weights between the analyte and mAbs realizes the separation of the free analyte by ultrafiltration. In addition, both enantiomers can be obtained by a simple one-step procedure where mAbs are prepared for each enantiomer.Herein, we report a convenient column-free methodology for chiral separation. This study provides insight on how to avoid difficulties when using mAbs. We chose a binaphthyl derivative with axial chirality, which is a well known asymmetric ligand, as a target ...

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Section: Figuresupporting

confidence: 69%

Direct Chiral Separation of Binaphthyl Derivatives Using Atroposelective Antibodies

et al. 2017

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“…( S ) -( − ) -Enantiomer of 1 is preferentially bound to BSA, developing a new absorption assignable to naphtholate anion at longer wavelengths, excitation of which leads to selective decomposition of ( S ) -( − ) -1 to enrich ( R ) -( + ) -1 in up to 99.5% ee after a 77% consumption of the starting material. 16,17 Zandomeneghi and coworkers examined the enantioselective photodecomposition of rac -ketoprofen ( 2 ) (Scheme 4.1 ) in the presence of BSA to obtain 80% ee after 99.8% of the starting material was photodecomposed. 18 Miranda and coworkers reported that the excited state of chiral ketoprofen 2 is quenched by thymidine and deoxyguanosine in an enantioselective manner, with accompanying Patern ò -B ü chi reaction and ketyl radical formation.…”

Section: Supramolecular Photochirogenesis With Biomoleculesmentioning

confidence: 99%

Supramolecular Photochirogenesis

Yang¹,

Inoue²

2011

Supramolecular Photochemistry

132

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“…In recent times, they have also found use as chiralbuilding blocks in coordination and metallosupramolecular chemistry [3][4][5]. Considerable interest in these complexes arises from the field of bioinorganic chemistry [5,6]. In addition, 2,2 0 -bipyridine is a well-known and important ligand.…”

Section: Introductionmentioning

confidence: 98%

Synthesis and cytotoxic activities of transition-metal complexes of a binaphthyl-linked bipyridine ligand

Beynek

Uluçam

Benkli

2009

Transition Met Chem

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A binaphthyl-linked bipyridyl compound, 1,1 0 -bis(6-methyl-6 0 -oxymethylenyl-2,2 0 -bipyridine)binaphthyl, (L) has been synthesised and used as a ligand for the formation of Cu(II), Ni(II), and Co(II) complexes. The ligand and its transition-metal complexes were characterized by physico-chemical and spectroscopic methods. The complexes were also investigated for cytotoxic activity. The cytotoxicity of complexes, CuL(ClO 4 ) 2 , NiL(ClO 4 ) 2 (H 2 O), CoL(ClO 4 ) 2 , were tested in vitro applying seven wellcharacterized human tumor cell lines, MCF7, EVSA-T, WIDR, IGROV, M19 MEL, A498, H226, and the microculture sulforhodamine B (SRB) test. All complexes show a very high cytotoxicity (ID 50 \ 250 ng/ml) in these cell lines.

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Complexation with albumins of chiral aromatic substrates and their chemistry in ground and excited states. Catalytic and chirality recognition properties of the protein in the cases of binaphthol, its photoisomers, and ketoprofen

Cited by 34 publications

References 28 publications

Direct Chiral Separation of Binaphthyl Derivatives Using Atroposelective Antibodies

Direct Chiral Separation of Binaphthyl Derivatives Using Atroposelective Antibodies

Supramolecular Photochirogenesis

Synthesis and cytotoxic activities of transition-metal complexes of a binaphthyl-linked bipyridine ligand

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