Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

Jones, Nigel A.; Rao, Dingqi; Yoshihara, Akihide; Gullapalli, Pushpakiran; Morimoto, Kenji; Takata, Goro; Hunter, Stuart J.; Wormald, Mark R.; Dwek, Raymond A.; Izumori, Ken; Fleet, George W. J.

doi:10.1016/j.tetasy.2008.07.034

Cited by 19 publications

(19 citation statements)

References 74 publications

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“…In these processes, the deoxy-sugar is first chemically hydrogenated towards the corresponding polyol, which then serves as substrate for the enzymatic oxidation. Microbial oxidation can also be performed on methylated polyols, for instance for production of both enantiomers of 4-C-methyl-ribulose by Gluconobacter thailandicus NBRC 3254 [46,92].…”

Section: Oxidoreductasesmentioning

confidence: 99%

“…At the laboratory scale, this enzyme has even been used to produce all possible ketohexoses [41,42]. Furthermore, D-TE is a highly promiscuous enzyme that can accept a large range of unnatural substrates, such as C-4-methylated pentoses [92], C-5-methylated hexoses [46], 5-deoxy-ketohexoses [90], and several 1-and 6-deoxy-ketohexoses [29]. Alternatively, immobilized D-TE has been applied in the mass production of D-psicose from D-fructose [107].…”

Section: Carbohydrate Epimerasesmentioning

confidence: 99%

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Enzymes for the biocatalytic production of rare sugars

Beerens

Desmet

Soetaert

2012

Journal of Industrial Microbiology and Biotechnology

168

109

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Carbohydrates are much more than just a source of energy as they also mediate a variety of recognition processes that are central to human health. As such, saccharides can be applied in the food and pharmaceutical industries to stimulate our immune system (e.g., prebiotics), to control diabetes (e.g., low-calorie sweeteners), or as building blocks for anticancer and antiviral drugs (e.g., L: -nucleosides). Unfortunately, only a small number of all possible monosaccharides are found in nature in sufficient amounts to allow their commercial exploitation. Consequently, so-called rare sugars have to be produced by (bio)chemical processes starting from cheap and widely available substrates. Three enzyme classes that can be used for rare sugar production are keto-aldol isomerases, epimerases, and oxidoreductases. In this review, the recent developments in rare sugar production with these biocatalysts are discussed.

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Section: Oxidoreductasesmentioning

confidence: 99%

Section: Carbohydrate Epimerasesmentioning

confidence: 99%

Enzymes for the biocatalytic production of rare sugars

Beerens

Desmet

Soetaert

2012

Journal of Industrial Microbiology and Biotechnology

168

109

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“…These enzymes are also used for the production of deoxyketohexoses (Gullapalli et al 2010;Rao et al 2009), methyl-ketohexoses (Jones et al 2008;Rao et al 2008), and some other rare sugars, including D-sorbose (Itoh et al 1995), L-xylulose (Uechi et al 2013b), L-tagatose, and L-fructose (Itoh and Izumori 1996). Although they exhibit broad substrate specificity toward various ketoses, the activities of many ketose 3-epimerases toward L-sugars have not been measured, probably due to the difficulty in obtaining Lsugars as substrates commercially.…”

Section: C-3 Epimerization Between L-ketohexosesmentioning

confidence: 99%

Advances in the enzymatic production of l-hexoses

Chen

Zhang

et al. 2016

Appl Microbiol Biotechnol

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Rare sugars have recently drawn attention because of their potential applications and huge market demands in the food and pharmaceutical industries. All L-hexoses are considered rare sugars, as they rarely occur in nature and are thus very expensive. L-Hexoses are important components of biologically relevant compounds as well as being used as precursors for certain pharmaceutical drugs and thus play an important role in the pharmaceutical industry. Many general strategies have been established for the synthesis of L-hexoses; however, the only one used in the biotechnology industry is the Izumoring strategy. In hexose Izumoring, four entrances link the D- to L-enantiomers, ketose 3-epimerases catalyze the C-3 epimerization of L-ketohexoses, and aldose isomerases catalyze the specific bioconversion of L-ketohexoses and the corresponding L-aldohexoses. In this article, recent studies on the enzymatic production of various L-hexoses are reviewed based on the Izumoring strategy.

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“…For branched sugars and their use as chirons, see: Rao et al (2008); Jones et al (2008); Booth et al (2008) ;Hotchkiss, Kato et al (2007); da Cruz et al (2008); Soengas et al (2005). For the structures of similar sugars, see: Chesterton et al (2006); Booth et al (2007); Hotchkiss, Jenkinson et al (2007); Baird et al (1987); Bruce et al (1990); Punzo et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

2-Azido-2-deoxy-3,4-O-isopropylidene-2-C-methyl-D-talono-1,5-lactone

et al. 2010

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The relative stereochemistry of the title compound, C10H15N3O5, was confirmed by the crystal structure determination. The absolute configuration was determined from the use of d-lyxonolactone as the starting material. The six-membered ring adopts a boat conformation with the larger azide group, rather than the methyl group, in the bowsprit position. In the crystal structure, a bifurcated intermolecular O—H⋯O/O—H⋯N hydrogen bond links molecules into chains running parallel to the b axis.

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Green syntheses of new 2-C-methyl aldohexoses and 5-C-methyl ketohexoses: d-tagatose-3-epimerase (DTE)—a promiscuous enzyme

Cited by 19 publications

References 74 publications

Enzymes for the biocatalytic production of rare sugars

Enzymes for the biocatalytic production of rare sugars

Advances in the enzymatic production of l-hexoses

2-Azido-2-deoxy-3,4-O-isopropylidene-2-C-methyl-D-talono-1,5-lactone

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