ChemicalBook CAS DataBase List (S)-3-HYDROXY-3-PHENYLPROPANOIC ACID

(S)-3-HYDROXY-3-PHENYLPROPANOIC ACID synthesis

8synthesis methods

Product Name:(S)-3-HYDROXY-3-PHENYLPROPANOIC ACID
CAS Number:36567-72-3
Molecular formula:C9H10O3
Molecular Weight:166.17

5764-85-2
83 suppliers
$20.00/1g

36567-72-3
38 suppliers
$66.89/250mg

(+)-ETHYL (R)-3-HYDROXY-3-PHENYLPROPIONATE

72656-47-4
17 suppliers
$286.64/1G

Yield:> 99 % ee

Reaction Conditions:

with Pseudomonas cepacia lipase in aq. phosphate buffer at 23; for 5 h;Catalytic behavior;Resolution of racemate;Enzymatic reaction;Reagent/catalyst;

Steps:

Kinetic resolution

General procedure: 10 mg of selected enzyme was incubated 45 min at 23 °C with 0.2 mL solution of 3.5 nm AuNPs, 0.1 mL solution of 20 nm AuNPs or 0.2 mL of water. Enzyme prepared in this way was added to 1 mL of PBS with 0.1 mmol of 3-hydroxy-3-phenylpropanoate. The mixture was shaking at 23 °C until conversion was about 50% (monitored with TLC). The mixture was extracted with diethyl ether and washed with saturated solution of sodium bicarbonate. Extract was dried with anhydrous magnesium sulfate, filtered and solvent was evaporated under reduced pressure. Recovered substrate was purified with column chromatography.(0013)In case of immobilized enzymes 0.3 mL of enzyme on AuNPs in PBS was added instead of 10 mg of enzyme incubated with AuNPs.(0014)Selected experiments were performed 5 times. Differences in conversion and enantiomeric excess were less than 5%.

References:

Jedrzejewska, Hanna;Ostaszewski, Ryszard [Journal of Molecular Catalysis B: Enzymatic,2013,vol. 90,p. 12 - 16]