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A Genetically Encodable Ligand for Transfer Hydrogenation
Author(s) -
Mayer Clemens,
Hilvert Donald
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300340
Subject(s) - chemistry , ligand (biochemistry) , transfer hydrogenation , tripeptide , formate , iridium , combinatorial chemistry , regioselectivity , imes , nad+ kinase , stereochemistry , catalysis , organic chemistry , peptide , biochemistry , ruthenium , enzyme , carbene , receptor
Simple tripeptides are shown here to be versatile ligands for iridium‐catalyzed transfer hydrogenations affording large acceleration effects. A water‐soluble iridium complex with Gly‐Gly‐Phe, for example, catalyzes the reduction of diverse ketones, aldehydes, and imines by formate with turnover frequencies rivaling or outperforming those of established ligand systems. Regioselective reduction of coenzyme NAD + to NADH illustrates the potential utility of this system for biotechnological applications. Because peptides are genetically encodable, they represent an attractive class of foldamer ligands for creating artificial metalloenzymes.