Ch_322b_24.04

Ch_322b_24.04 - L-amino acid derivative with a deacylase DL-RCHCO 2-NH 3 racemic mixture CH 3 COCCH 3 O = O acetylation DL-RCHCO 2 H NH CCH 3 O

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Resolution of DL-Amino Acids All of the synthetic methods presented so far yield racemic forms of chiral ! -amino acids. With the exception of glycine, all the natural ! -amino acids have a stereocenter of the L-configuration: CH 2 -CO 2 - NH 3 + glycine RCH-CO 2 - NH 3 + * chiral ! -amino acid CO 2 - R H H 3 N + L-configuration C H 3 N + H CO 2 - R
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Enzymatic Resolution Racemic mixtures of ! -amino acids may be resolved by enzymes called deacylases . These enzymes catalyze the hydrolysis of N-acylamino acids of the L-configuration . The strategy involves acetylating both the D- and L-amino acids, and then selectively hydrolyzing the
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Unformatted text preview: L-amino acid derivative with a deacylase. DL-RCHCO 2-NH 3 + racemic mixture CH 3 COCCH 3 O = O acetylation DL-RCHCO 2 H NH CCH 3 O deacylase CO 2-R H H 3 N + L-amino acid CH 3 COOH + CO 2-R H NH CCH 3 O D-N-acetyl amino acid separable Stereoselective Synthesis of Amino Acids In this approach, only a single enantiomer of a chiral amino acid is produced by using a chiral reagent or catalyst. This methodolgy is more generally called enantioselective synthesis ....
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This note was uploaded on 01/23/2011 for the course CHEM 322BL taught by Professor Singer during the Spring '07 term at USC.

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Ch_322b_24.04 - L-amino acid derivative with a deacylase DL-RCHCO 2-NH 3 racemic mixture CH 3 COCCH 3 O = O acetylation DL-RCHCO 2 H NH CCH 3 O

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