ChemInform Abstract: CHIRAL SYNTHESIS OF A COMPONENT OF AMANITA MUSCARIA, (‐)‐4‐HYDROXYPYRROLIDIN‐2‐ONE, AND ASSESSMENT OF ITS ABSOLUTE CONFIGURATION

Abstract

Reduktion des Keto ‐ esters (I) mit NaBH4 ergibt den Alkohol (11), der mit Hydrazin (III) das Pyrrolidon (IV) liefert.

Purification and Properties of a Carbonyl Reductase Useful for Production of Ethyl (S)-4-Chloro-3-hydroxybutanoate from Kluyveromyces lactis

“…ethyl (S )-4-chloro-3-hydroxybutanoate; fatty acid synthase Ethyl (S )-4-chloro-3-hydroxybutanoate ((S )-ECHB) is a chiral building block useful for the synthesis of pharmacologically and biologically important compounds, such as hydroxymethylglutaryl-CoA (HMG-CoA) reductase inhibitors 1) and 4hydroxypyrrolidone. 2) Asymmetric reduction with enantioselective oxidoreductases is one of practical methods for the production of (S )-ECHB. Several enzymes that reduce ethyl 4-chloroacetoacetate (ECAA) to (S )-ECHB have been found and puriˆed from Saccharomyces cerevisiae, 3) Geotrichum candidum, 4) Sporobolomyces salmonicolor, 5) Candida macedoniensis, 6) and Candida magnoliae.…”

A novel carbonyl reductase from Pichia stipitis for the production of ethyl (S)-4-chloro-3-hydroxybutanoate

“…pharmacologically active compounds such as hydroxymethylglutaryl-CoA reductase inhibitors (Karanewsky et al 1990) and 4-hydroxypyrrolidone (Santaniello et al 1984). The reduction of ethyl 4-chloro-3-oxobutanoate (COBE) is a more economical way of producing (S)-CHBE because COBE is easily synthesized and cheap (Yasohara et al 1999).…”

A Novel NADH-Dependent Carbonyl Reductase fromKluyveromyces aestuariiand Comparison of NADH-Regeneration System for the Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutanoate

“…Tel: +81-29-856-1322; Fax: +81-29-856-1323; E-mail: h-yamamoto@daicel.co.jp Abbreviations: ADH, alcohol dehydrogenase; CR, carbonyl reductase; KaCR1, carbonyl reductase 1 from Kluyveromyces aestuarii; ECAA, ethyl 4-chloroacetoacetate; ECHB, ethyl 3-hydroxybutanoate; FDH, formate dehydrogenase; GDH, glucose dehydrogenase inhibitors 11) and 4-hydroxypyrrolidone. 12) Several enzymes reducing ethyl 4-chloroacetoacetate (ECAA) to (S)-ECHB have been found and purified from Candida macedoniensis, 13) Candida magnoliae, 14) Geotrichum candidum, 15) Kluyveromyces lactis, 16) Saccharomyces cerevisiae, 17) and S. salmonicolor; 18) furthermore, -ketoacyl-acyl carrier protein (ACP) reductases and acetoacetyl-CoA reductases were reported to reduce ECAA to (S)-ECHB with high enantioselectivity. 8) All of the carbonyl reductases listed above, however, were NADPH-dependent and the regeneration of a coenzyme using FDH cannot be applied to the production of (S)-ECHB using these enzymes.…”