Details

Autor(en) / Beteiligte

• Ford, Grayson J.
• Swanson, Christopher R.
• Bradshaw Allen, Ruth T.
• Marshall, James R.
• Mattey, Ashley P.
• Turner, Nicholas J.
• Clapés, Pere
• Flitsch, Sabine L.

Titel

Three-Component Stereoselective Enzymatic Synthesis of Amino-Diols and Amino-Polyols

Ist Teil von

• JACS Au, 2022-10, Vol.2 (10), p.2251-2258

Ort / Verlag

American Chemical Society

Erscheinungsjahr

2022

Quelle

Free E-Journal (出版社公開部分のみ）

Beschreibungen/Notizen

• Amino-polyols represent attractive chemical building blocks but can be challenging to synthesize because of the high density of asymmetric functionalities and the need for extensive protecting-group strategies. Here we present a three-component strategy for the stereoselective enzymatic synthesis of amino-diols and amino-polyols using a diverse set of prochiral aldehydes, hydroxy ketones, and amines as starting materials. We were able to combine biocatalytic aldol reactions, using variants of d-fructose-6-phosphate aldolase (FSA), with reductive aminations catalyzed by IRED-259, identified from a metagenomic library. A two-step process, without the need for intermediate isolation, was developed to avoid cross-reactivity of the carbonyl components. Stereoselective formation of the 2R,3R,4R enantiomers of amino-polyols was observed and confirmed by X-ray crystallography.