Bioprocess and Biosystems Engineering 2006-04-01

Effect of organic cosolvent on kinetic resolution of tert-leucine by penicillin G acylase from Kluyvera citrophila.

Shu-Lai Liu, Dong-Zhi Wei, Qing-Xun Song, Ye-Wang Zhang, Xue-Dong Wang

Index: Bioprocess Biosyst. Eng. 28(5) , 285-9, (2006)

Full Text: HTML

Abstract

Penicillin G acylase (PGA) from Kluyvera citrophila immobilized on Amberzyml was used for enantioselective hydrolysis of N-phenylacetylated-DL-tert-leucine (N-Phac-DL-Tle) to produce L-tert-leucine (L-Tle). The effects of various organic cosolvents on hydrolysis of N-Phac-DL-Tle have been investigated in aqueous-cosolvent medium. It was founded that the rate of PGA-catalyzed reaction was significantly affected by the presence of 2% (v/v) organic cosolvent concentration. The initial rate fell with increasing logP of the cosolvent, but for logP values less than -0.24 the rate was faster than in purely aqueous medium. Additionally, the relative rate increases with the increase of dielectric constant (epsilon) of organic cosolvents. The yields of L-Tle in all aqueous-cosolvent systems were above 95% with the enantiomeric excess (ee) of >99%.

Related Compounds

  • L-tert-Leucine
  • 3-Methylvaline

Related Articles:

Highly selective asymmetric acetate aldol reactions of an N-acetyl thiazolidinethione reagent.

2004-01-08

[Org. Lett. 6 , 23-25, (2004)]

Scaleable catalytic asymmetric Strecker syntheses of unnatural alpha-amino acids.

2009-10-15

[Nature 461(7266) , 968-70, (2009)]

An efficient and selective enzymatic oxidation system for the synthesis of enantiomerically pure D-tert-leucine.

2003-10-02

[Org. Lett. 5(20) , 3649-50, (2003)]

Preferred conformations of peptides containing tert-leucine, a sterically demanding, lipophilic alpha-amino acid with a quaternary side-chain Cbeta atom.

2005-04-08

[Chemistry 11(8) , 2395-404, (2005)]

The tert-butyl group in chemistry and biology.

2008-08-07

[Org. Biomol. Chem. 6(15) , 2655-65, (2008)]

More Articles...