Benzyl (S)-(-)-tetrahydro-5-oxo-3-furanylcarbamate

White or off-white powder or crystal

General procedure: Owing to the problems that both ketones 1k, l and their corresponding lactones 2k, l showed when analyzed by GC, as well as their poor solubility in diethyl ether or ethyl acetate, their enzymatic transformations were carried out in a bigger scale (3, 2 mL tubes) but maintaining identical reaction conditions. After 24 h, products were extracted with deuterated chloroform (2400 μL). The organic phases were dried over anhydrous sodium sulfate, filtered and conversion values were determined by 1H NMR experiments. Similarly, samples were evaporated and the residue re-dissolved in a mixture of hexane:ethanol 90:10 for HPLC analyses (see Tables S20-S21). In a typical experiment carried out in 1.5 mL tubes (total volume of 500 μL), the substrate 1a-j, m-v (10 mM) was dissolved in methanol (5 μL, 1percent v/v) and KPi buffer (100 mM, pH 9.0, 482 μL), containing glucose (20 mM), glucose dehydrogenase (GDH-105, 10 U, from stock solution of 1.275 U/μL), NADPH (0.2 mM, from a 20 mM stock solution) and the corresponding Baeyere-Villiger monooxygenase (2 mg). The mixture was shaken at 250 rpm at 30 °C for 24 h. The reaction was stopped by extracting with diethyl ether (2x400 μL) and centrifugedat 13, 000 rpm in order to separate both phases and pellet the suspended protein. The organic phases were combined, dried over anhydrous sodium sulfate and analyzed by GC in order to determine the conversion values. Then, the solvent in GC samples was evaporated with a continuous flow of nitrogen, the residue redissolved in a mixture of hexane:ethanol 90:10 and the new sample filtered and analyzed by HPLC, leading to the measurement of the enantiomeric excess of the lactones. Control experiments in the absence of enzyme were performed for all substrates, not observing any reaction product after similar periods of time (Tables S1-S19).General procedure: Owing to the problems that both ketones 1k, l and their corresponding lactones 2k, l showed when analyzed by GC, as well as their poor solubility in diethyl ether or ethyl acetate, their enzymatic transformations were carried out in a bigger scale (3, 2 mL tubes) but maintaining identical reaction conditions. After 24 h, products were extracted with deuterated chloroform (2400 μL). The organic phases were dried over anhydrous sodium sulfate, filtered and conversion values were determined by 1H NMR experiments. Similarly, samples were evaporated and the residue re-dissolved in a mixture of hexane:ethanol 90:10 for HPLC analyses (see Tables S20-S21). In a typical experiment carried out in 1.5 mL tubes (total volume of 500 μL), the substrate 1a-j, m-v (10 mM) was dissolved in methanol (5 μL, 1percent v/v) and KPi buffer (100 mM, pH 9.0, 482 μL), containing glucose (20 mM), glucose dehydrogenase (GDH-105, 10 U, from stock solution of 1.275 U/μL), NADPH (0.2 mM, from a 20 mM stock solution) and the corresponding Baeyere-Villiger monooxygenase (2 mg). The mixture was shaken at 250 rpm at 30 °C for 24 h. The reaction was stopped by extracting with diethyl ether (2x400 μL) and centrifugedat 13, 000 rpm in order to separate both phases and pellet the suspended protein. The organic phases were combined, dried over anhydrous sodium sulfate and analyzed by GC in order to determine the conversion values. Then, the solvent in GC samples was evaporated with a continuous flow of nitrogen, the residue redissolved in a mixture of hexane:ethanol 90:10 and the new sample filtered and analyzed by HPLC, leading to the measurement of the enantiomeric excess of the lactones. Control experiments in the absence of enzyme were performed for all substrates, not observing any reaction product after similar periods of time (Tables S1-S19).

Molecular Weight:235.24
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:235.08445790
Monoisotopic Mass:235.08445790
Topological Polar Surface Area:64.6
Heavy Atom Count:17
Complexity:286
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes