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Organic synthesis

DOS fragments grow hits in several directions at once

Kidd SL, Fowler E, Reinhardt T, et al. · Chemical science · 2020

Open access · cc by · source: Europe PMC

A modular diversity-oriented fragment library gave crystallographic hits on several proteins and then short, cheap sequences to many analogues, including a first covalent PBP3 fragment.

Key findings

Compound 1 was the first binder after ~1300 prior fragment soaks on PBP3, covalently linking Ser294. Up to 14 analogues per hit were accessible; only p-fluoro analogue 28 of nine aromatics soaked into CFI crystals; 1,4-isoxazole 29 bound but 1,5-isomer 30 did not.

Methodology

Authors screened a racemic DOS fragment set (500 mM in d6-DMSO) by X-ray crystallography, then used designed exit vectors—amide couplings, click chemistry, Cu(I) lactonizations—to elaborate hits such as the PBP3 covalent binder 1.

Limitations

The paper does not report optimized cellular potency or a clinical candidate—only early crystallographic hits and synthetic tractability.

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