Fermentation route for the production of levulinic acid, levulinate esters and valerolactone and derivatives thereof

Inventors

Zanghellini, Alexandre Luc

Assignees

Arzeda Corp

Abstract

The invention provides processes for the conversion of pyruvate obtained from sugars or other carbon sources, to valuable C5 materials such as levulinic acid, levulinate esters, valerolactone, and derivatives thereof.

Core Innovation

The invention relates to a method for producing C5 materials from pyruvate through conversion steps that include aldol addition and subsequent redox transformations. Pyruvate is converted to 4-hydroxy-2-oxo-pentanoic acid by aldol addition, and the intermediate is then converted to 2,4-dihydroxy-pentanoic acid through chemical or enzymatic reduction.

The described pathway includes named keto-hydroxy and dihydroxy intermediates such as 4-hydroxy-2-oxo-pentanoic acid and 2,4-dihydroxy-pentanoic acid, and it further supports conversion variants that may include oxidative dehydration to form 4-oxo-2-pentenoic acid. Related transformations include reductions and oxidations as part of moving between 4-oxo and hydroxy states, and dehydration steps that generate unsaturated intermediates prior to further reductions.

The document also describes branching and downstream derivatization options for the C5 intermediates and products. The route can include cyclization of dihydroxy acids to lactones, such as conversion to 2-hydroxy-4-valerolactone, and it can include formation of CoA-thioester intermediates by attaching CoA to form 2,4-dihydroxy-pentanoyl-CoA. The pathway framework is supported by enzyme classes including pyruvate decarboxylase and class I/class II aldolases, along with dehydrogenases, dehydratases, enoate reductases, and lactonases.

Claims Coverage

The provided claim set includes one independent claim directed to producing 2,4-dihydroxy-pentanoic acid and dependent claims that specify additional conversion steps, intermediates, and system features. The independent claim centers on two core inventive features: an aldol addition conversion from pyruvate to a keto-hydroxy intermediate, followed by reduction to 2,4-dihydroxy-pentanoic acid.

Overall claim coverage is anchored on forming 4-hydroxy-2-oxo-pentanoic acid from pyruvate via aldol addition and then reducing that intermediate to 2,4-dihydroxy-pentanoic acid using chemical or enzymatic reduction. Dependent claims further cover conversion variants, including oxidative dehydration and cyclization to lactones, and derivatization through CoA attachment to form CoA-thioester intermediates.

Stated Advantages

Documented Applications