Extension of dibenzoyl tartaric acid-based optical resolutions to a subpreparative scale by applying magnetic enantioseparation

Jávor, Bálint and Szegedi, Dorka and Ádám, Bálint Árpád and Hakkel, Orsolya and Illés, Levente and Fürjes, Péter and Tóth, Tünde and László, Szabolcs and Golcs, Ádám (2026) Extension of dibenzoyl tartaric acid-based optical resolutions to a subpreparative scale by applying magnetic enantioseparation. SEPARATION AND PURIFICATION TECHNOLOGY, 389. No. 136924. ISSN 1383-5866

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Abstract

This study presents a high-throughput enantioenrichment method based on DBTA-functionalized magnetic microparticles (MMPs) for the optical resolution of racemic amines, alcohols and amino alcohols at the nanomolar–low micromolar scale. The separation relies on the formation of diastereomeric host–guest adducts through a combination of salt formation and coordination-type non-covalent interactions. Systematic variation of the linker architecture revealed that conformationally rigid, silica-supported systems provide superior selector accessibility and stereochemical discrimination. Using optimized MMPs, enantioenrichment with enantiomeric excess values of up to ∼50% per separation step was achieved under standardized conditions (5% DMSO–water, ambient temperature, 30 min contact time), while maintaining broad substrate applicability. The method enables parallel processing of up to 96 samples, requires only milligram-scale particle quantities per well, and operates without compound-specific optimization. Independent chiral HPLC validation confirmed good agreement with polarimetric ee determination (deviations within ±10%). These results demonstrate that the proposed platform offers a rapid and operationally simple alternative for first-pass enantioenrichment and prioritization in automated early-stage discovery workflows, complementing conventional preparative and instrumentally intensive enantioseparation techniques.

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