Microbial transformation of 2-hydroxy and 2-acetoxy ketones with Geotrichum sp.

Wei, Zhi-Liang; Lin, Guo‐Qiang; Li, Zu‐Yi

doi:10.1016/s0968-0896(00)00023-7

Cited by 53 publications

(16 citation statements)

References 51 publications

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“…The (S)-specific carbonyl reductase (SCR, also known as S-specific alcohol dehydrogenase) from Candida parapsilosis is an NADPH-dependent member of the classical enzyme family of short-chain dehydrogenases/reductases (SDRs) and has strong potential for biotechnological applications (Wei et al 2000). It is the only known SDR that catalyzes the enantioselective reduction of 2-hydroxyacetophenone to produce the valuable, optically active 1-phenyl-1, 2-ethanediol with high yield and chiral purity (Wei et al 2000;Cao et al 2006;Supplemental Fig.…”

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Crystal structure of a carbonyl reductase from Candida parapsilosis with anti‐Prelog stereospecificity

et al. 2008

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A novel short-chain (S)-1-phenyl-1,2-ethanediol dehydrogenase (SCR) from Candida parapsilosis exhibits coenzyme specificity for NADPH over NADH. It catalyzes an anti-Prelog type reaction to reduce 2-hydroxyacetophenone into (S)-1-phenyl-1,2-ethanediol. The coding gene was overexpressed in Escherichia coli and the purified protein was crystallized. The crystal structure of the apo-form was solved to 2.7 Å resolution. This protein forms a homo-tetramer with a broken 2-2-2 symmetry. The overall fold of each SCR subunit is similar to that of the known structures of other homologous alcohol dehydrogenases, although the latter usually form tetramers with perfect 2-2-2 symmetries. Additionally, in the apo-SCR structure, the entrance of the NADPH pocket is blocked by a surface loop. In order to understand the structure-function relationship of SCR, we carried out a number of mutagenesisenzymatic analyses based on the new structural information. First, mutations of the putative catalytic Ser-Tyr-Lys triad confirmed their functional role. Second, truncation of an N-terminal 31-residue peptide indicated its role in oligomerization, but not in catalytic activity. Similarly, a V270D point mutation rendered the SCR as a dimer, rather than a tetramer, without affecting the enzymatic activity. Moreover, the S67D/H68D double-point mutation inside the coenzyme-binding pocket resulted in a nearly 10-fold increase and a 20-fold decrease in the k cat /K M value when NADH and NADPH were used as cofactors, respectively, with k cat remaining essentially the same. This latter result provides a new example of a protein engineering approach to modify the coenzyme specificity in SCR and short-chain dehydrogenases/reductases in general.

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confidence: 99%

“…It is the only known SDR that catalyzes the enantioselective reduction of 2-hydroxyacetophenone to produce the valuable, optically active 1-phenyl-1, 2-ethanediol with high yield and chiral purity (Wei et al 2000;Cao et al 2006;Supplemental Fig. 1).…”

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confidence: 99%

Crystal structure of a carbonyl reductase from Candida parapsilosis with anti‐Prelog stereospecificity

et al. 2008

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“…Only a few microorganisms were found to possess anti-Prelog selectivity, such as Geotrichum spp. (36), Yarrowia lipolytica (5), Lactobacillus brevis (6), Lactobacillus kefiri (3), and Pseudomonas spp. (2).…”

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Purification, Characterization, Gene Cloning, and Expression of a Novel Alcohol Dehydrogenase with Anti-Prelog Stereospecificity from Candida parapsilosis

Nie

et al. 2007

Appl Environ Microbiol

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An alcohol dehydrogenase from Candida parapsilosis CCTCC M203011 was characterized along with its biochemical activity and structural gene. The amino acid sequence shows similarity to those of the short-chain dehydrogenase/reductases but no overall identity to known proteins. This enzyme with unusual stereospecificity catalyzes an anti-Prelog reduction of 2-hydroxyacetophenone to (S)-1-phenyl-1,2-ethanediol.

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“…They have recently been used to prepare photosensitive derivatives of biologically active compounds which can be studied in a complex system such as a living cell, 17) but the use of their optical form has been seriously hampered because no e‹cient way has existed to obtain them with high enantiomeric excess. The best results obtained have been a 46z yield with 89zee 18) for chiral o-nitrostyrene and a 37z yield with 47z ee for the corresponding diol 19) in previous reports. In the course of our work, the kinetic resolution of onitrostyrene oxide was studied as shown in Fig.…”

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confidence: 81%

Microbial transformation of 2-hydroxy and 2-acetoxy ketones with Geotrichum sp.

Cited by 53 publications

References 51 publications

Crystal structure of a carbonyl reductase from Candida parapsilosis with anti‐Prelog stereospecificity

Crystal structure of a carbonyl reductase from Candida parapsilosis with anti‐Prelog stereospecificity

Purification, Characterization, Gene Cloning, and Expression of a Novel Alcohol Dehydrogenase with Anti-Prelog Stereospecificity from Candida parapsilosis

Enantioselective Hydrolysis ofo-Nitrostyrene Oxide by Whole Cells ofAspergillus nigerCGMCC 0496

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