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ChemicalBook CAS DataBase List (S)-p-Chlorophenyl-phenylMethanaMine

(S)-p-Chlorophenyl-phenylMethanaMine synthesis

9synthesis methods
-

Yield: > 99 % ee

Reaction Conditions:

with pyridoxal 5'-phosphate;transaminase-3;piruvate in dimethyl sulfoxide; pH=9 at 30;Enzymatic reaction;enantioselective reaction;Reagent/catalyst;

Steps:

Determination of activity in kinetic resolution mode.
General procedure: The activity measurements were performed in a TECAN Infinite 200 PRO reader, and all measurements were performed at least in triplicate. A direct photometric assay was used28, in which the enzymatic reaction took place in CHES buffer (50 mM, pH 9.0) at 30 °C in a total volume of 200 μl. 1 mM racemic amine (1a-4a) and 2 mM pyruvate were added to the buffer (final concentrations) containing the TA of interest. Due to the preparation of the amine stock solution in organic solvent, 5% (vol/vol) 2-propanol or dimethylsulfoxide (DMSO, 0.1% for compounds 5-7) was present in the final reaction medium. The kinetic resolution was initiated by the addition of the amine acceptor (pyruvate). The final concentration of the enzyme varied between 2 and 800 μg ml-1, depending on the specific activity towards the substrates under examination. The production of the corresponding ketones (1b-7b) was monitored at the optimum wavelength for each compound (1b, 16,562M-1 cm-1 at 264 nm; 2b, 9,646 M-1 cm-1at 245 nm; 3b, 5,714 M-1 cm-1 at 340 nm; 4b, 6,115 M-1 cm-1 at 245 nm (ref. 27);5b and 6b, 6,530 M-1 cm-1 at 242 nm (ref. 15); and 7b, 7,098 M-1 cm-1at 252 nm (ref. 14)).

References:

Pavlidis, Ioannis V.;Weiß, Martin S.;Genz, Maika;Spurr, Paul;Hanlon, Steven P.;Wirz, Beat;Iding, Hans;Bornscheuer, Uwe T. [Nature Chemistry,2016,vol. 8,# 11,p. 1076 - 1082]