Biocatalytic method for producing 2h-hbo and ß-substituted analogues from lgo using a cyclohexanone monooxygenase
OwnerFlorent Allais, Louis Mouterde +1inventors
InventorsFlorent Allais, Louis Mouterde, John Dale Stewart
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Abstract
An eco-compatible method is used to synthesize 2H-HBO optionally substituted at the β-position of the lactone function from LGO or a saturated form of LGO such as dihydrolevoglucosenone (2H-LGO) or LGO hydrate (OH-LGO) via a biocatalytic reaction using a cyclohexanone monooxygenase (CHMO).
Claims20
A method for synthesis of 4-hydroxymethyl-γ-butyrolactone (2H-HBO), optionally substituted at the β position of the lactone function, from levoglucosenone (LGO) in saturated form, represented by formula (I),
- wherein R represents an H or OH, NH2, SH, linear, cyclic or branched alkyl, OR1 (where R1 is a linear, cyclic or branched alkyl, silyl, acyl, benzyl, benzoyle), NHR1 (where R1 is a linear, cyclic or branched alkyl), NR1R2 (where R1 and R2 are a linear, cyclic or branched alkyl), SR1 (where R1 is a linear, cyclic or branched alkyl), or thioacetal group,
- wherein the method comprises a biocatylasis reaction using a cyclohexanone monooxygenase followed by an acid hydrolyis.
A method for synthesizing 4-hydroxymethyl-γ-butyrolactone (2H-HBO) from levoglucosenone (LGO), comprising placing, into the same reactive medium, an enzyme that allows for a conversion of the LGO into 2H-LGO and an enzyme that allows for the conversion of 2H-LGO into a molecule of 4-hydroxymethyl-γ-butyrolactone (2H-HBO), the enzyme for conversion of 2H-LGO into 4-hydroxymethyl-γ-butyrolactone (2H-HBO) being a cyclohexanone monooxygenase.
Dependencies are inferred from the claim text.