Highly Enantioselective Reduction of Carbonyl Compounds Using a Reductase Purified from Bakers' Yeast

Abstract

An NADPH-dependent reductase that shows reducing activity for 1-chloro-2-hexanone has been purified from bakers' yeast. SDS−PAGE and gel filtration suggested that the purified reductase is a monomeric enzyme with a molecular weight of ca. 37 kDa. Asymmetric reduction of several carbonyl compounds using the purified reductase has been carried out. 1-Chloro-2-hexanone, 1-acetoxy-2-heptanone, methyl acetoacetate, ethyl pyruvate, 1-chloro-2,4-pentanedione, and 2,4-hexanedione were reduced to the corresponding alcohols with high enantiomeric purities (>98% ee). The reductase showed high specificity constants (k cat/K m = 103−105 s-1 M-1) and relatively low Michaelis constants (K m = 10-4−10-3 M) for all the substrates examined.

An evaluation of methyl 2‐oxocyclopentanecarboxylate as an iron(III) trap: food perspectives

“…are the photosynthetic pigments and electron-transfer molecules (Doonan, 1969). Some micro-organisms can metabolize these substrates (Ema et al, 1998) and, therefore it seems reasonable to think that these compounds might be degraded more easily than other ligands, such as ethylenediaminetetraacetate (EDTA), which has been proposed recently as a fortificant in certain grain-based products including breakfast cereals and cereal bars (Satroutdinov et al, 2000).…”

“…These chelating agents have important applications such as control of bitterness and the property of stabilizing foam (Blanco et al, 2003), while the b-hydroxy derivatives that are produced can be useful building blocks in antibiotics and pheromone biosynthesis (Ema et al, 1998).…”

“…Baker's yeast (Saccharomyces cerevisiae) has been shown to reduce carbonyl groups in cyclic 1,3ketoesters and cyclic 1,3-diketones to optically active alcohols (Bel-Rhlid et al, 1992). These chelating agents have important applications such as control of bitterness and the property of stabilizing foam (Blanco et al, 2003), while the b-hydroxy derivatives that are produced can be useful building blocks in antibiotics and pheromone biosynthesis (Ema et al, 1998).…”

Dicarbonyl reduction by single enzyme for the preparation of chiral diols

“…21 Moreover, Gre2p could reduce a variety of mono-ketones with different substitutions, including a-chloro ketones, a-acetoxy ketones, a-keto esters, b-keto esters and g-keto esters. 34,45 Despite the fact that the binding pocket of Gre2p could accommodate a bulky ester or a hydrophobic group, aliphatic esters were much better than those with an aromatic ring. If an electron withdrawing substituent, such as chlorine, was located next to the carbonyl group, the activity of Gre2p increased 4-fold.…”

Yeast‐mediated enantioselective synthesis of chiral R‐(+)‐ and S‐(−)‐1‐phenyl‐1‐butanol from prochiral phenyl n‐propyl ketone in hexane–water biphasic culture

“…The importance of chiral alcohols and their derivatives can be attributed to their serving as the chiral building blocks of pheromones,4 fragrance,5 pharmaceuticals and other chemicals 6–9. The enantioselective synthesis of chiral alcohols can be achieved using catalytic organometallic reagents; however, chiral alcohol production using either whole yeast cell10, 11 or isolated alcohol dehydrogenase,12, 13 either immobilized14, 15 or not immobilized,16, 17 is still favored for reasons of stability and ease of product recovery.…”