Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata

Gotor, Vicente; Rebolledo, Francisca; Liz, Ramón

doi:10.1016/s0957-4166(01)00048-9

Cited by 53 publications

(18 citation statements)

References 18 publications

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“…2‐(Butylsulfonyl)‐1‐phenylethanone (3h) : A white solid; mp 79–80 °C (Ref. 71–73 °C); IR (KBr) 1688, 1321, 1133 cm −1 ; 1 H NMR (CDCl 3 ) δ 0.98 (t, 1H , J = 7.3 Hz), 1.46–1.55 (m, 2H), 1.84–1.92 (m, 2H), 3.26 (t, 2H, J = 8.2 Hz), 4.57 (s, 2H), 7.52 (bt, 2H, J = 7.8 Hz), 7.65 (bt, 1H, J = 7.6 Hz), 8.02 (bd, 2H, J = 7.3 Hz).…”

Section: Methodsmentioning

confidence: 99%

One‐Pot Synthesis of β‐Keto Sulfones by the Condensative Decarboxylation of Sulfonylacetic Acids with Acid Chlorides under Mild Conditions

Lee

2015

Bulletin Korean Chem Soc

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Section: Methodsmentioning

confidence: 99%

One‐Pot Synthesis of β‐Keto Sulfones by the Condensative Decarboxylation of Sulfonylacetic Acids with Acid Chlorides under Mild Conditions

Lee

2015

Bulletin Korean Chem Soc

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“…306,307 One recent example of enzymatic reduction of β-ketosulfones by a whole cell system is the reduction of β-ketosulfone groups bearing bulky substituents by the fungus Culvaria lunata with an enantiomer excess of 97%. 320 Examples of Baker's yeast mediated resolutions of 2-keto sulfides, sulfoxide and sulfones are depicted in FigureBaker' …”

Section: Baker's Yeast Reduction Of Sulfur Containing Compoundsmentioning

confidence: 99%

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

Milner¹,

Maguire²

2012

Arkivoc

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Modern synthetic organic chemistry has experienced an enormous growth in biocatalytic methodologies; enzymatic transformations and whole cell bioconversions have become generally accepted synthetic tools for asymmetric synthesis. This review details an overview of the latest achievements in biocatalytic methodologies for the synthesis of enantiopure compounds with a particular focus on chemoenzymatic synthesis in non-aqueous media, immobilisation technology and dynamic kinetic resolution. Furthermore, recent advances in ketoreductase technology and their applications are also presented.Keywords: Biocatalysis, kinetic and dynamic kinetic resolution, Baker's yeast, ketoreductases General IntroductionAsymmetric synthesis is the preferential formation of one stereoisomer of a chiral target compound to another; when scientists at GlaxoSmithKline, AstraZeneca and Pfizer 1 examined 128 syntheses from their companies, they found as many as half of the drug compounds made by their process research and development groups are not only chiral but also contain an average of two chiral centres each. 2In 2006 just 25 % were derived from the chiral pool and over 50 % employed chiral technologies. 1In order to meet regulatory requirements enantiomeric purities of 99.5 % were deemed necessary by the FDA. 3 This is one of the biggest challenges which face chemists today, primarily due to the recognition of the fact that different enantiomers of the same compound can interact differently in biological systems. As a consequence, the production of single enantiomers instead of racemic mixtures has become an important process in the pharmaceutical and agrochemical industry. Several routes can lead to the desired enantiomer including transition metal-, [4][5][6] organo-5,7-10 and bio-catalysis [11][12][13][14][15] and these have been thoroughly reviewed in the literature. 16,17 2. Biocatalysis IntroductionBiocatalysis involves the use of enzymes or whole cells (containing the desired enzyme or enzyme system) as catalysts for chemical reactions. A timeline of historic events in biocatalysis and biotechnology is outlined in Table 1. [18][19][20] Reviews and Accounts Novel methodologies for discovering industrial enzymes based on genomic sequencing and phage display (discussed further in Section 1.3), 21,22 as well as highly effective optimisation tools based on chemical, physical and molecular biology approaches, 23 have improved the access to biocatalysts, increased their stability, and radically broadened their specificity. 24This greater availability of catalysts with superior qualities including the use of new bioengineering tools contributed significantly to the development of new industrial processes. Biocatalytic methodologies for organic synthesis were outlined by Woodley et al. in three categories: established, emerging and expanding chemistries as depicted in Figure 1. 25 Enzyme classesBy the late 1950s it had become evident that the nomenclature of enzymes without any guiding authority, in a period when the...

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“…However, a primary issue in using biocatalysts for desymmetrization is that it is difficult to predict which organism is going to give the required transformation generating the desired enantiomeric form. Curvularia lunata has also been utilized for the reduction of a range of prochiral -keto sulfones [64] (Fig. Recently [62] a rapid screening methodology has been reported, using microwell plates and targeting enantioselective ketone reduction utilizing specific microbial libraries.…”

Section: Fungal Modification Of Side-chains Side-chain Ketone Reductimentioning

confidence: 99%

The Current Chemical Utility of Marine and Terrestrial Filamentous Fungi in Side-Chain Chemistry

Hunter¹

2007

COC

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This review focuses on three aspects of the application of marine and terrestrial filamentous fungi to side-chain chemistry from 2000 to early 2006. The first section covers the generation of novel biologically active side-chain containing metabolites. This includes a range of antibiotic, cytotoxic and novel bioactive compounds. The second section discusses the use of these fungi both whole cell and lipases of fungal origin in the chemical modification of side-chains. Examples include reductive desymmetrization of pro-chiral ketones, dynamic kinetic resolution and unique reactions. The final section details the degradation of side-chains by fungi and includes lignin and steroid transformations for determination metabolism and the generation of new skeletal structure.

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Enantioselective bioreduction of β-keto sulfones with the fungus Curvularia lunata

Cited by 53 publications

References 18 publications

One‐Pot Synthesis of β‐Keto Sulfones by the Condensative Decarboxylation of Sulfonylacetic Acids with Acid Chlorides under Mild Conditions

One‐Pot Synthesis of β‐Keto Sulfones by the Condensative Decarboxylation of Sulfonylacetic Acids with Acid Chlorides under Mild Conditions

Recent trends in whole cell and isolated enzymes in enantioselective synthesis

The Current Chemical Utility of Marine and Terrestrial Filamentous Fungi in Side-Chain Chemistry

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