Abstract Chiral transition metal oxides nanoparticles (NPs) with tunable optical properties are widely accepted as promising toolbox for chiral recognition, stereoselective synthesis, and chiroptical devices. Herein, chirality‐based strategy is presented for discrimination of d ‐glucose from its enantiomer through a cooperative synergy between chiral cysteine capped MoO 2 NPs and the glucose oxidase nanosystem. The valence‐state‐dependent chirality induced by metal‐ligand charge transfer effect is found to be ultrasensitive to its redox environment such as the presence of hydrogen peroxide, which is a key indicator of the stereoselective enzymatic reaction between glucose oxidase and d ‐glucose. With this know‐how, glucose enantiomers can be precisely quantified with a limit of detection of 0.446 µ m . Such a chiral bio‐nanosystem would be an ideal platform for a rational design of new types of biosensors, photocatalysts, and chirality‐based nanodevices.