Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate

  title={Marine Microorganisms as Source of Stereoselective Esterases and Ketoreductases: Kinetic Resolution of a Prostaglandin Intermediate},
  author={V. D. Vitis and B. Guidi and Martina L. Contente and T. Granato and P. Conti and F. Molinari and E. Crotti and F. Mapelli and S. Borin and D. Daffonchio and D. Romano},
  journal={Marine Biotechnology},
A screening among bacterial strains isolated from water-brine interface of the deep hypersaline anoxic basins (DHABs) of the Eastern Mediterranean was carried out for the biocatalytical resolution of racemic propyl ester of anti-2-oxotricyclo[]heptan-7-carboxylic acid (R,S)-1, a key intermediate for the synthesis of d-cloprostenol. Bacillus horneckiae 15A gave highly stereoselective reduction of (R,S)-1, whereas Halomonas aquamarina 9B enantioselectively hydrolysed (R,S)-1; in both cases… Expand
Organic Solvent-Tolerant Marine Microorganisms as Catalysts for Kinetic Resolution of Cyclic β-Hydroxy Ketones
This report describes a straightforward approach to enantiomerically enriched (R)- and (S)-3-hydroxycyclopentanone 2a, (R- and ( S-3-Hydroxycyclohexanone) 2b, and (R) and (C) involving a transesterification resolution of the racemates using whole cells of marine microorganisms as catalysts and vinyl acetate the acyl donor and solvent. Expand
A Comparative Study on Asymmetric Reduction of Ketones Using the Growing and Resting Cells of Marine-Derived Fungi
This is the first study to perform asymmetric reduction of ketones by one-step growing cell biotransformation and shows a capacity to be recycled nine times without a significant decrease in the activity. Expand
Seawater‐Based Biocatalytic Strategy: Stereoselective Reductions of Ketones with Marine Yeasts
The large consumption of freshwater in fermentations and bio‐transformations is a matter of concern for the sustainability of many bio‐processes. The use of seawater to perform bio‐processes is aExpand
The use of marine-derived fungi for preparation of enantiomerically pure alcohols
An evaluation of the synthetic potential of 13 Chinese marine fungi was performed to screen for enantioselective reduction of 13 aromatic ketones from different compound classes as substrates, and ketone reductases from two prioritized fungi exhibited good recyclability. Expand
Immobilized and Free Cells of Geotrichum candidum for Asymmetric Reduction of Ketones: Stability and Recyclability
The stabilities—in terms of pH tolerance, thermostability, and storage stability, and reusability— of G. candidum AS 2.361 were described for the asymmetric reduction of a series of aromatic ketones. Expand
Applications of Marine-Derived Microorganisms and Their Enzymes in Biocatalysis and Biotransformation, the Underexplored Potentials
This review presents studies employing whole-cell processes of marine bacteria and fungi, aiming for new catalysts for different reactions in organic synthesis, such as reduction, oxidation, hydroxylation, hydrolysis, elimination, and conjugation. Expand
Esterases as stereoselective biocatalysts.
Non-lypolitic esterases are carboxylester hydrolases with preference for the hydrolysis of water-soluble esters bearing short-chain acyl residues. The potential of esterases as enantioselectiveExpand
Marine Microorganisms for Biocatalysis: Selective Hydrolysis of Nitriles with a Salt-Resistant Strain of Meyerozyma guilliermondii
Nitrilase from M. guilliermondii LM2 (UBOCC-A-214008) displayed high activity on aromatic substrates, but also arylaliphatic and aliphatic substrates were accepted and hydrolysis of nitriles was efficiently performed using a bioprocess entirely carried out in seawater. Expand
Deep Hypersaline Anoxic Basins as Untapped Reservoir of Polyextremophilic Prokaryotes of Biotechnological Interest
The current knowledge on prokaryotic diversity in DHABs is reviewed, highlighting the biotechnological applications of identified taxa and isolated species and the discovery of new species and molecules from these ecosystems is expanding the understanding of life limits. Expand
Strategic single point mutation yields a solvent- and salt-stable transaminase from Virgibacillus sp. in soluble form
A new transaminase (VbTA) was identified from the genome of the halotolerant marine bacterium Virgibacillus 21D and it was revealed that this mutation is crucial for correct dimerisation and thus correct folding, leading to soluble protein expression. Expand


A new chemoenzymatic synthesis of D-cloprostenol
Abstract A new chemoenzymatic synthesis of d -cloprostenol based on the biocatalytical resolution of anti -2-oxotricyclo[]heptan-7-carboxylic acid 1 has been developed. The resolution wasExpand
Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
Abstract The enantioselective hydrolysis of different ( RS )-1,2- O -isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the ( S )-alcohol asExpand
Microbial enzymes mined from the Urania deep-sea hypersaline anoxic basin.
Five esterases are characterized from the brine:seawater interface of the Urania hypersaline basin and some of them have high activities, specificities, enantioselectivities, and exceptional stability in polar solvents, and they are therefore potentially useful for industrial biotransformations. Expand
3-(Hydroxy(phenyl)methyl)azetidin-2-ones obtained via catalytic asymmetric hydrogenation or by biotransformation
Abstract The catalytic asymmetric reduction of ethyl-2-(benzamidomethyl)-3-oxo-phenylpropanoate was realized with high enantiomeric and diastereoisomeric excesses via biotransformation using wholeExpand
Cloning, expression and characterization of a new enantioselective esterase from a marine bacterium Pelagibacterium halotolerans B2T
Abstract An esterase, designated as PE8 (219 aa, 23.19 kDa), was cloned from a marine bacterium Pelagibacterium halotolerans B2T and overexpressed in Escherichia coli Rosetta, resulting an active,Expand
Enantioselective hydrolysis of (RS)-isopropylideneglycerol acetate with Kluyveromyces marxianus
Abstract The hydrolysis of ( RS )-isopropylideneglycerol acetate with whole cells of the yeast Kluyveromyces marxianus is reported. The biotransformation furnished ( R )-isopropylideneglycerol asExpand
Synthesis of chiral pharmaceutical intermediates by biocatalysis
Chiral intermediates were prepared by biocatalytic processes for the chemical synthesis of four pharmaceutical drug candidates. These include: (i) the microbial reduction of 3,5-dioxo-6-(benzyloxy)Expand
Asymmetric reductions of ethyl 2-(benzamidomethyl)-3-oxobutanoate by yeasts
Abstract The stereoselective reduction of ethyl 2-(benzamidomethyl)-3-oxobutanoate 1 using yeasts was investigated among a restricted number (12) of yeasts. Kluyveromyces marxianus var. lactis CL69Expand
Enzymatic hydrolysis of capsaicins for the production of vanillylamine using ECB deacylase from Actinoplanes utahensis
Echinocandin acylase from Actinoplanes utahensis NRRL 12052 (ECB deacylase) was used for the hydrolysis of capsaicins (trans-8-methyl-N-vanillyl-6-nonenamide and 8-methyl-N-vanillyl-6-nonanamide)Expand
Marine Biocatalysts: Enzymatic Features and Applications
The analysis of literature cited here and the many published patent applications concerning the use of marine enzymes supports the view that these biocatalysts are just waiting to be discovered, reflecting the importance of the marine environment. Expand