Enantioselective synthesis of cyanohydrins catalysed by hydroxynitrile lyases - a review.

نویسندگان

  • Paula Bracco
  • Hanna Busch
  • Jan von Langermann
  • Ulf Hanefeld
چکیده

The first enantioselective synthesis was the selective addition of cyanide to benzaldehyde catalysed by a hydroxynitrile lyase (HNL). Since then these enzymes have been developed into a reliable tool in organic synthesis. HNLs to prepare either the (R)- or the (S)-enantiomer of the desired cyanohydrin are available and a wide variety of reaction conditions can be applied. As a result of this, numerous applications of these enzymes in organic synthesis have been described. Here the examples of the last decade are summarised, the enzyme catalysed step is discussed and the follow-up chemistry is shown. This proves HNLs to be part of main stream organic synthesis. Additionally the newest approaches via immobilisation and reaction engineering are introduced.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins.

Hydroxynitrile lyases (HNLs) catalyze the cleavage of cyanohydrins. In the reverse reaction, they catalyze the formation of carbon-carbon bonds by enantioselective condensation of hydrocyanic acid with carbonyls. In this study, we describe two proteins from endophytic bacteria that display activity in the cleavage and the synthesis reaction of (R)-mandelonitrile with up to 74% conversion of ben...

متن کامل

Hydroxynitrile lyases: At the interface of biology and chemistry

Hydroxynitrile lyases are the versatile group of enzymes, which play a significant defensive role in plant system against microbial attack. In chemical industries, hydroxynitrile lyase is used as an important industrial biocatalyst for the synthesis of chiral cyanohydrins by exploiting the reversible enzymatic reaction. Cyanohydrins are biologically active compounds used in synthesis of -amino ...

متن کامل

Hydroxynitrile Lyases, Interesting Biocatalysts in Stereoselective Organic Syntheses

Hydroxynitrile lyases (HNLs) from Prunus amygdalus (PaHNL), Sorghum bicolor (SbHNL), Manihot esculenta (MeHNL) and Hevea brasiliensis (HbHNL) are excellent biocatalysts for the preparation of optically active cyanohydrins. (R)as well as (S)-cyanohydrins are obtained in high optical and chemical yields. The synthetic potential of the now easily available optically pure cyanohydrins is demonstrat...

متن کامل

Substrate Binding in the FAD-Dependent Hydroxynitrile Lyase from Almond Provides Insight into the Mechanism of Cyanohydrin Formation and Explains the Absence of Dehydrogenation Activity†,‡

In a large number of plant species hydroxynitrile lyases catalyze the decomposition of cyanohydrins in order to generate hydrogen cyanide upon tissue damage. Hydrogen cyanide serves as a deterrent against herbivores and fungi. In vitro hydroxynitrile lyases are proficient biocatalysts for the stereospecific synthesis of cyanohydrins. Curiously, hydroxynitrile lyases from different species are c...

متن کامل

Efficient Synthesis and Analysis of Chiral Cyanohydrins

This thesis deals with the development of new methods for efficient synthesis and analysis in asymmetric catalysis. It focuses on the preparation of chiral cyanohydrins by enantioselective addition of cyanide to prochiral aldehydes. The initial part of the thesis describes the development of a dual Lewis acid– Lewis base activation system for efficient synthesis of chiral O-acylated and Ocarbon...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Organic & biomolecular chemistry

دوره 14 27  شماره 

صفحات  -

تاریخ انتشار 2016