A palladium-catalyst stabilized in the chiral environment of a monoclonal antibody in water

Kobayashi, Yuichiro; Murata, Keisuke; Harada, Akira; Yamaguchi, Hiroyasu

doi:10.1039/c9cc08756g

Cited by 12 publications

(11 citation statements)

References 37 publications

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“…Furthermore, asymmetric environments in water often carry transcendent performance that cannot be exerted in organic solvents [6] . Chiral precious‐metal complexes have, however, rarely been used in aqueous media, [1b,k, 6–10] in spite of an increasing awareness that performing organic reactions in water meets the worldwide need for green sustainable chemistry. The problem may lie with the insolubility and inherent ease of hydrolysis of these complexes in water because soft acids are reluctant to coordinate with the hard base H 2 O and furthermore they exhibit low hydrolysis constants (e.g.…”

Section: Methodsmentioning

confidence: 99%

“…Applications of chiral palladium complexes to reactions in aqueous media include examples of complexes embedding into a protein scaffold, [6a, 8] a robust PEPPSI complex, [9] a complex supported on an amphiphilic resin, [10] and a micellar system [11] . We envisaged a complementary approach wherein a chiral hydrogen‐bond donor associated with trifluoromethanesulfonate (triflate) anion would furnish a charge‐separated palladium aqua complex with enhanced Lewis acidity (Scheme 1 b).…”

Section: Methodsmentioning

confidence: 99%

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Hydrogen‐Bonding‐Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water

et al. 2020

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Metal‐bound water molecules have recently been recognized as a new facet of soft Lewis acid catalysis. Herein, a chiral palladium aqua complex was constructed that enables carbon–hydrogen bonds of indoles to be functionalized efficiently. We embraced a chiral 2,2′‐bipyridine as both ligand and hydrogen‐bond donor to configure a robust, yet highly Lewis acidic, chiral aqua complex in water. Whereas the enantioselectivity could not be controlled in organic solvents or under solvent‐free conditions, the use of aqueous environments allowed the σ‐indolylpalladium intermediates to react efficiently in a highly enantioselective manner. This work thus describes a potentially powerful new approach to the transformation of organometallic intermediates in a highly enantioselective manner under mild reaction conditions.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Hydrogen‐Bonding‐Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water

et al. 2020

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“…Other unusual chelator structures have been designed to prepare antibodies for transition metal complexes (e.g. Rh(I) and Pd(II)) and Ru(II) (Kobayashi et al, 2020;Shreder et al, 1996;Yamaguchi et al, 2006).…”

Section: Metal Ions Haptenmentioning

confidence: 99%

Antibody developments for metal ions and their applications

Wang

Zhang

Liu

2020

Food and Agricultural Immunology

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Metal ions are beneficial or toxic in part depending on their identity, valence state, and concentration. Antibodies against radioactive metal ions can be used in medical diagnosis and therapy, while antibodies against heavy metal ions are widely used in the trace element analysis of the immunoassay. This review focuses on the recent advances in antibody developments for metal ions and their applications. We exhaustively enumerated 18 chelate or ligand structures for metal hapten synthesis, which were proven to produce antibodies that cover almost 33 metal ions. The binding properties of these antibodies for their corresponding haptens were also discussed both in the structural foundation and molecular foundation. Furthermore, the representative applications of the antibodies used in medical diagnostics and therapy, and immunoassays were summarized. Finally, we illustrated the present challenges in high specific metal ion antibody preparation, and in immunoassay development. The future perspectives were also discussed.

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“…For metals like palladium, a number of seminal studies have developed ArMs to improve the enantioselectivity of reactions like Suzuki cross-coupling, [177][178] Mizoroki-Heck reaction, 179 allylic alkylation, 180 and allylic amination. 181 Other breakthrough studies have also focused on the use of vanadium, 182 chromium, 183 osmium, 184 cobalt, [185][186][187][188][189][190][191] nickel, [192][193][194][195][196] and zinc. [197][198][199]…”

Section: New-to-nature Reactions Of Armsmentioning

confidence: 99%

Exploring and Adapting the Molecular Selectivity of Artificial Metalloenzymes

Vong

Nasibullin

Tanaka

2020

Bulletin of the Chemical Society of Japan

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In recent years, artificial metalloenzymes (ArMs) have become a major research interest in the field of biocatalysis. With the ability to facilitate new-to-nature reactions, researchers have generally prepared them either through intensive protein engineering studies or through the introduction of abiotic transition metals. The aim of this review will be to summarize the major types of ArMs that have been recently developed, as well as to highlight their general reaction scope. A point of emphasis will also be made to discuss the promising ways that the molecular selectivity of ArMs can be applied to in areas of pharmaceutical synthesis, diagnostics, and drug therapy.

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A palladium-catalyst stabilized in the chiral environment of a monoclonal antibody in water

Abstract: We report the first preparation of a monoclonal antibody (mAb) that can immobilize a palladium (Pd)-complex. The allylic amination reaction using a supramolecular catalyst of the Pd-complex with mAb selectively gives the (R)-enantiomer product.

Cited by 12 publications

References 37 publications

Hydrogen‐Bonding‐Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water

Hydrogen‐Bonding‐Assisted Cationic Aqua Palladium(II) Complex Enables Highly Efficient Asymmetric Reactions in Water

Antibody developments for metal ions and their applications

Exploring and Adapting the Molecular Selectivity of Artificial Metalloenzymes

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