Stereoinversion of amino acids in a single reactor

A process to stereoinvert a first enantiomer into a second enantiomer in a single reactor, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst, thereby resulting in an intermediate;
• and
• b) combining the intermediate, a second catalyst, a reductant, and an amine source thereby resulting in the second enantiomer;
• wherein step (a) and step (b) take place at different times.

A process to stereoinvert a first enantiomer into a second enantiomer in a single reactor that includes a first surface and a second surface, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in an intermediate;
• and
• b) combining the intermediate, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein the first surface and the second surface are different and step (a) or step (b) is performed first;
• step (a) is complete before step (b) begins;
• and step (a) and step (b) are performed at or near different sites within the reactor.

A process to stereoinvert a first enantiomer into a second enantiomer in a single reactor that includes a first surface and a second surface, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in at least one of a keto acid intermediate or an imine intermediate;
• and
• b) combining the at least one of a keto acid intermediate or an imine intermediate, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein the first surface and the second surface are different and the first catalyst and the second catalyst are prevented from contacting each other;
• the first catalyst is an enantioselective amino acid oxidase that is specific for at least one of a D-amino acid or an L-amino acid;
• the second catalyst is a metal catalyst that includes palladium on carbon;
• the reductant includes hydrogen gas;
• and the amine source comprises ammonia or an ammonium salt.

A process to stereoinvert a first enantiomer into a second enantiomer in a reactor that includes a first surface and a second surface, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in an intermediate;
• and
• b) combining the intermediate, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein the first catalyst and the second catalyst are prevented from contacting each other;
• and the first surface or the second surface is removable from the reactor.

A process to stereoinvert a first enantiomer into a second enantiomer in a reactor that includes a first surface and a second surface, comprising the steps of:

• a1) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in an intermediate keto acid;
• a2) preventing decarboxylation of the keto acid during the oxidizing step;
• and
• b) combining the intermediate keto acid, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein the first catalyst and the second catalyst are prevented from contacting each other;
• the preventing step takes place in the presence of a catalase;
• and the catalase is attached to a removable surface.

A process to stereoinvert a first enantiomer into a second enantiomer in a reactor that includes a first surface and a second surface, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in an intermediate;
• and
• b) combining the intermediate, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein the first catalyst and the second catalyst are prevented from contacting each other;
• the reactor comprises one of the group consisting of a stirred tank reactor, a fermentation vessel, a hollow fiber membrane bioreactor, an oscillatory baffled reactor, and a counter current chromatographic reactor;
• and the oxidizing step and the reducing step are carried out as a continuous process.

A process to stereoinvert a first enantiomer into a second enantiomer in a reactor that includes a first surface and a second surface, comprising the steps of:

• a) combining the first enantiomer, oxygen, and a first catalyst that is in contact with the first surface, thereby resulting in an intermediate;
• and
• b) combining the intermediate, a second catalyst that is in contact with the second surface, a reductant, and an amine source, thereby resulting in the second enantiomer;
• wherein step (a) or step (b) is performed first;
• step (a) is complete before step (b) begins;
• and step (a) and step (b) are performed at or near different sites within the reactor;
• and the first surface or the second surface is removable from the reactor.