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Cellulose-derived levoglucosenone ( LGO ) has been efficiently converted into pure ( S )-γ-hydroxymethyl-α,β-butenolide ( HBO ), a chemical platform suited for the synthesis of drugs, flavors and antiviral agents. This process involves two-steps: a lipase-catalyzed Baeyer-Villiger oxidation of  LGO  followed by an acid hydrolysis of the reaction mixture to provide pure  HBO . Response surface methodology (RSM), based on central composite face-centered (CCF) design, was employed to evaluate the factors effecting the enzyme-catalyzed reaction: pka of solid buffer (7.2–9.6),  LGO  concentration (0.5–1 M) and enzyme loading (55–285 PLU.mmol -1 ). Enzyme loading and pka of solid buffer were found to be important factors to the reaction efficiency (as measured by the conversion of  LGO ) while only the later had significant effects on the enzyme recyclability (as measured by the enzyme residual activity).  LGO  concentration influences both responses by its interaction with the enzyme loading and pka of solid buffer. The optimal conditions which allow to convert at least 80% of  LGO  in 2 h at 40°C and reuse the enzyme for a subsequent cycle were found to be: solid buffer pka = 7.5,  [LGO]  = 0.50 M and 113 PLU.mmol -1  for the lipase. A good agreement between experimental and predicted values was obtained and the model validity confirmed ( p  < 0.05). Alternative optimal conditions were explored using  Monte Carlo  simulations for risk analysis, being estimated the experimental region where the  LGO  conversion higher than 80% is fulfilled at a specific risk of failure.

frontiers in chemistry

Lipase-Catalyzed Baeyer-Villiger Oxidation of Cellulose-Derived Levoglucosenone into (S)-γ-Hydroxymethyl-α,β-Butenolide: Optimization by Response Surface Methodology