2 publications

2 publications

A Palladium-Catalyst Stabilized in the Chiral Environment of a Monoclonal Antibody in Water

Arada, H.; Yamaguchi, H.

Chem. Commun. 2020, 56, 1605-1607, 10.1039/c9cc08756g

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.

Metal: Pd
Ligand type: Allyl; Phosphine
Host protein: Antibody
Anchoring strategy: Supramolecular
Optimization: ---
Reaction: Allylic amination
Max TON: 600
ee: 98
PDB: ---
Notes: Recalculated TON

Atroposelective Antibodies as a Designed Protein Scaffold for Artificial Metalloenzymes

Harada, A.; Yamaguchi, H.

Sci. Rep. 2019, 9, 10.1038/s41598-019-49844-0

Design and engineering of protein scaffolds are crucial to create artificial metalloenzymes. Herein we report the first example of C-C bond formation catalyzed by artificial metalloenzymes, which consist of monoclonal antibodies (mAbs) and C2 symmetric metal catalysts. Prepared as a tailored protein scaffold for a binaphthyl derivative (BN), mAbs bind metal catalysts bearing a 1,1?-bi-isoquinoline (BIQ) ligand to yield artificial metalloenzymes. These artificial metalloenzymes catalyze the Friedel-Crafts alkylation reaction. In the presence of mAb R44E1, the reaction proceeds with 88% ee. The reaction catalyzed by Cu-catalyst incorporated into the binding site of mAb R44E1 is found to show excellent enantioselectivity with 99% ee. The protein environment also enables the use of BIQ-based catalysts as asymmetric catalysts for the first time.

Metal: Cu; Pd; Pt
Ligand type: Bipyridine
Host protein: Antibody
Anchoring strategy: Antigen
Optimization: Genetic
Max TON: 2
ee: 88
PDB: ---
Notes: ---