Methylenemalonic acid and intermediates, processes for their preparation and engineered microorganisms
AssigneeLcy Biosciences Inc.
InventorsMAN KIT LAU, CATHY STALOCH HASS, JAMES R. MILLIS
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Abstract
The description relates to, inter alia, recombinant microorganisms, engineered metabolic pathways, chemical catalysts, and products produced through the use of the described methods and materials. The products produced include methylenemalonic acid and intermediates, as well as their salts and esters.
Claims61
A recombinant microorganism comprising 2-hydroxymethylmalonic acid, and at least one recombinant nucleic acid sequence encoding at least one enzyme selected from a CoA carboxylase and a CoA hydrolase, wherein the 2-hydroxymethylmalonic acid is a compound of Formula II:
- or a salt or ester thereof.
A method for making a methylenemalonic acid of Formula I:
- or a salt or ester thereof;
- the method comprising treating a compound of Formula II:
- or a salt or ester thereof;
- by heating and/or contacting with a catalyst to dehydrate the compound of Formula II to produce a compound of Formula I, or its salt or ester.
A recombinant microorganism comprising 2,3-dioxobutyric acid or acetoacetic acid or a salt or ester thereof and at least one recombinant nucleic acid sequence encoding at least one enzyme selected from a CoA-hydrolase, a thiolase and an alcohol dehydrogenase.
A method for making a methylenemalonic acid of Formula I:
- or a salt or ester thereof;
- the method comprising treating a methyltartronic acid of Formula III:
- or a salt or ester thereof;
- by heating and/or contacting with a catalyst, optionally followed by pyrolysis, to dehydrate the compound of Formula III and/or contacting with a bromination agent followed by an elimination agent such as a base, to produce methylenemalonic acid or a salt or ester thereof.
A recombinant microorganism comprising methylmalonic acid and at least one recombinant nucleic acid sequence encoding at least one enzyme selected from a CoA carboxylase and a CoA hydrolase, wherein said methylmalonic acid is a compound of Formula IV:
- or a salt or ester thereof.
A method for making a methylenemalonic acid of Formula I:
- or a salt or ester thereof;
- the method comprising treating a compound of Formula IV:
- or a salt or ester thereof;
- by heating in the presence of O2 and/or contacting with a catalyst to dehydrogenate the compound of Formula IV to produce the methylenemalonic acid or a salt or ester thereof.
A recombinant microorganism comprising methylenemalonic acid or a salt or ester thereof, and at least one recombinant nucleic acid sequence encoding at least one enzyme selected from a transaminase, a synthase, an alcohol dehydrogenase, a semialdehyde dehydrogenase, a dehydratase and a decarboxylase.
A compound of the formula:
- or a salt or ester thereof.
Dependencies are inferred from the claim text.