A Photoregulated Racemase Mimic. Issue 10 (12th January 2021)

• Record Type: Journal Article
• Authors: Saha, Monochura; Hossain, Munshi Sahid; Bandyopadhyay, Subhajit
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 10(2021)
• Page Start: 5220
• Page End: 5224
• Publication Date: 2021-01-12
• Subjects: azobenzene -- biomimetic -- photochemistry -- photochromism -- racemase; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202012124
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The racemase enzymes convert L ‐amino acids to their D ‐isomer. The reaction proceeds through a stepwise deprotonation–reprotonation mechanism that is assisted by a pyridoxal phosphate (PLP) coenzyme. This work reports a PLP–photoswitch–imidazole triad where the racemization reaction can be controlled by light by tweaking the distance between the basic residue and the reaction centre. Abstract : The cis isomer of an azobenzene‐based artificial pyridoxal phosphate (PLP) racemase effectively deprotonates and racemizes L ‐alanine. A histidinyl unit bearing an imidazole group in close proximity to the racemizable Cα ‐H of the L ‐alanine aldimine residue is responsible for racemization using light as the stimulus. The trans isomer is less effective in terms of deprotonation and racemization.