Enantioselectivity of Candida rugosa lipase toward carboxylic acids: A predictive rule from substrate mapping and x-ray crystallography was written by Ahmed, Sharmin N.;Kazlauskas, Romas J.;Morinville, Anne H.;Grochulski, Pawel;Schrag, Joseph D.;Cygler, Miroslaw. And the article was included in Biocatalysis in 1994.Product Details of 7476-66-6 This article mentions the following:
Substrate mapping was used to develop a rule that predicts which enantiomer of chiral carboxylic acid esters reacts faster in hydrolyses catalyzed by lipase from Candida rugosa (CRL). This rule, based on the size of the substituents at the stereocenter, is not reliable for crude CRL. It predicts the favored enantiomer for only 23 of 34 examples, 68% reliability. However, this rule is completely reliable for purified CRL; it predicts the favored enantiomer for all 16 examples correctly. The examples include arylpropanoic acids, aryloxypropanoic acids, α-halophenylacetic acids, mandelic acid and O-methylmandelic acid. Further, purified CRL did not catalyze the hydrolysis of N-CBZ-phenylalanine Me ester and N-CBZ-norleucine Me ester. These 2 substrates were exceptions to the rule with crude CRL as the catalyst. Besides eliminating several exceptions, purification also raised the enantioselectivity of CRL toward carboxylic acid esters. To provide a structural basis for this proposed rule, the x-ray crystal structure of CRL containing transition state analogs of ester hydrolysis was examined It was suggested that the large substituent of chiral carboxylic acids binds in a tunnel that normally binds the alkyl chain of a fatty acid. The Ph rings of Phe 345 and Phe 415 lie close to the stereocenter, thereby fixing the orientation of the medium substituent. The 3-dimensional orientation of these proposed binding sites is consistent with the rule derived from substrate mapping. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6Product Details of 7476-66-6).
Methyl 2-chloro-2-phenylacetate (cas: 7476-66-6) belongs to organic chlorides. An organic chloride is an organic compound containing at least one covalently bonded atom of chlorine. Their wide structural variety and divergent chemical properties lead to a broad range of names and applications. Organochlorine compounds are lipophylic, meaning they are more soluble in fat than in water. This gives them a high tenancy to accumulate in the food chain (biomagnification).Product Details of 7476-66-6
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics