Synthesis of 4-Sulfur-Substituted (2<i>S</i>,3<i>R</i>)-3-Phenylserines by Enzymatic Resolution. Enantiopure Precursors for Thiamphenicol and Florfenicol

Kaptein, Bernard; Dooren, T. J. G. M. van; Boesten, W. H. J.; Sonke, Theo; Duchateau, Alexander L. L.; Broxterman, and Quirinus B.; Kamphuis, J.

doi:10.1021/op970045t

Cited by 31 publications

(8 citation statements)

References 21 publications

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“…It is worthy to note that, regardless of medicinal importance of sulfones much attention has earlier been paid towards chemoselective oxidation of sulfides to sulfoxides and the protocols developed for the same have been extended towards the synthesis of sulfones. Nitric acid [122], KMnO4 [123], bromine [124], NaOCl [125], ozone [126], peracids [127][128][129], t-BuOOH [130] are few of the oxidants used in early days. Few reports are also available on the use of magnesium monoperoxyphthalate (MMPP) [131] and polyvalent [132] and hypervalent iodine compounds [133][134][135].…”

Section: Non-oxidative Routesmentioning

confidence: 99%

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Kupwade

2019

J. Chem. Rev.

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A large variety of organosulfur compounds have been shown to having diverse biological effects such as antioxidant effects, anti-inflammatory properties, inhibition of platelet aggregation, reduction of systolic blood pressure, and reduction of cholesterol. Among these, sulfoxides and sulfones show wide and significant applications as commodity chemical in various fields of chemistry. Therefore, synthesis of sulfoxides as well as sulfones has remained a point of attraction for synthetic organic chemists. Among array of methods used to synthesize the sulfoxides or sulfones, oxidation of sulfide is the most convenient way. This review precises chemoselective methods for the synthesis of the sulfoxides as well as sulfones focusing on oxidative protocols. This review will aid researchers to explore and utilise the mentioned protocols for different organic transformations.

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Section: Non-oxidative Routesmentioning

confidence: 99%

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Kupwade

2019

J. Chem. Rev.

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“…Simply by performing the hydrolysis reaction at slightly acidic conditions the solubility of the amide substrates increases due to the presence of the protonizable amino group. This feature has been employed in the resolution of the racemic threophenylserine amides 103a/b, which are intermediates in a novel route to the antibiotics thiamphenicol (104a) and florfenicol (104b), of which only the (1R,2R)-enantiomers display the required biological activity [304]. In this case, the O. anthropi amidase-catalyzed resolution reaction was performed at pH 5.6-6.0 to ensure a fair solubility of the otherwise insoluble amides.…”

Section: Ncimb 40321mentioning

confidence: 99%

“…The (2S,3R)-phenylserines were obtained in >99% e.e. and chemical yields up to 50% [304]. Another example can be found in the preparation of (S)-a-methyl-(3,4-dichlorophenyl)alanine (105) from the corresponding racemic amide.…”

Section: Ncimb 40321mentioning

confidence: 99%

Hydrolysis of Amides

Sonke

Kaptein

2012

Enzyme Catalysis in Organic Synthesis

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“…The enzymatic resolution of the corresponding racemic amide runs at a substrate input of 20 g/L and gave the desired α -amino acid in 41% yield and with 99.4% ee. Furthermore, biocatalytic resolution of α -amino acids bearing two stereogenic centers has been done by means of amidases, and was applied, for example, for the synthesis of an intermediate of the pharmaceutically important antibiotics fl orfenicol and thiamphenicol [101] . An α -amino -ε -caprolactam racemase turned out to be suitable for the racemization of a broad range of acyclic amides besides caprolactam.…”

Section: Amide Hydrolysismentioning

confidence: 99%

Enzyme‐Catalyzed Asymmetric Synthesis

Gröger

2010

Catalytic Asymmetric Synthesis

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INTRODUCTIONBiocatalysis has been recognized over the past decades as a highly valuable tool for organic chemists to prepare enantiomerically pure molecules, so -called chiral building blocks, in a highly effi cient way. Besides a multitude of academic work, it is noteworthy that enzyme catalysis belongs to the standard repertoire in industry when facing challenging enantioselective synthetic routes. A broad range of biocatalytic methods is already in use in particular for large -scale manufacture of drug intermediates [1] .The research in the fi eld of enzyme catalysis has already been comprehensively reviewed some years ago [2] . Thus, the focus of the current review is on a selection of (particularly recently developed) enantioselective enzymatic reactions, which turned out to be highly useful and applicable in organic synthesis, fulfi lling criteria such as high productivity, substrate concentrations, conversions, and enantioselectivities. The presented methods are an interesting complementary tool to existing " classic organic " or " chemocatalytic asymmetric " methodologies. Among biocatalytic reactions, both resolution of racemates and asymmetric synthesis starting from prochiral substrates are attractive routes already applied, in part, in industry. A third type of biotechnological approach, which is not a subject of this review, are fermentation processes. A graphical summary of these three types of so -called " white biotechnology " methodologies is given in Scheme 6.1 .Hydrolases are the enzyme class most commonly applied as biocatalysts in organic chemistry. This is mainly due to the accessibility of these enzymes (used, e.g., in the textile and detergents industry), their suitability for transformations in organic media Catalytic Asymmetric Synthesis, Third Edition, Edited by Iwao Ojima 269 270 ENZYME-CATALYZED ASYMMETRIC SYNTHESIS (in particular when using lipases), and the lack of a need for cofactors. However, in recent years, we have also seen an increasing tendency to apply redox enzymes in organic syntheses as well as lyases in C -C bond formations and transferases. Isomerases also turned out to be very useful in particular in combination with hydrolases for dynamic kinetic resolutions. Thus, a broad range of biotransformations is available for organic chemists. A challenge, however, is the use of ATP cofactor -dependent enzymes, which contribute to only a negligible number of typical organic biotransformations (e.g., due to the high price of ATP).The fi eld of biocatalysis benefi ted signifi cantly from the tremendous progress in molecular biology. Highly effi cient methods for screening and optimization of biocatalysts (by, e.g., directed evolution in the latter case) have been developed, which allows access to tailor -made enzymes. Furthermore, the design of recombinant microorganisms gives access to highly productive whole -cell catalysts, which contain only the desired enzymes in large amount, thus signifi cantly reducing the required biomass for biotransformations compared with the use of...

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Synthesis of 4-Sulfur-Substituted (2S,3R)-3-Phenylserines by Enzymatic Resolution. Enantiopure Precursors for Thiamphenicol and Florfenicol

Cited by 31 publications

References 21 publications

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

A Concise Review on Synthesis of Sulfoxides and Sulfones with Special Reference to Oxidation of Sulfides

Hydrolysis of Amides

Enzyme‐Catalyzed Asymmetric Synthesis

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