A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase—a reagent that is both specific and general

Rao, Dingqi; Best, Daniel; Yoshihara, Akihide; Gullapalli, Pushpakiran; Morimoto, Kenji; Wormald, Mark R.; Wilson, Francis X.; Izumori, Ken; Fleet, George W. J.

doi:10.1016/j.tetlet.2009.03.061

Cited by 25 publications

(17 citation statements)

References 54 publications

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“…Many microbial enzymes have been reported to be biocatalysts for the production of rare sugars. [25][26][27][28][29][30][31][32]38,41,42) Here, we report the successful production of three 6-deoxy-aldohexoses, 6-deoxy-L-glucose, 6-deoxy-L-altrose, and 6-deoxy-L-allose, by the use of four aldose isomerases and DTE reactivities. In its entirety, our procedure, which uses L-rhamnose as starting material, resulted in production yields of 5.4, 14.6, and 25.1%, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…All 12 of the 5-deoxyhexoses and 10 of the 16 1-and 6-deoxyketohexoses were successfully produced in our laboratory, by a combination of chemical and biotechnological methods. 27,28) We are currently investigating whether the D-arabinose isomerase (D-AI), L-arabinose isomerase (L-AI), L-ribose isomerase (L-RI), and DTE produced in our laboratory act on 6-deoxy monosaccharides.…”

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confidence: 99%

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Enzymatic production of three 6-deoxy-aldohexoses from l-rhamnose

Shompoosang

Yoshihara

Uechi

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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6-Deoxy-l-glucose, 6-deoxy-l-altrose, and 6-deoxy-l-allose were produced from l-rhamnose with an immobilized enzyme that was partially purified (IE) and an immobilized Escherichia coli recombinant treated with toluene (TT). 6-Deoxy-l-psicose was produced from l-rhamnose by a combination of l-rhamnose isomerase (TT-PsLRhI) and d-tagatose 3-epimerase (TT-PcDTE). The purified 6-deoxy-l-psicose was isomerized to 6-deoxy-l-altrose and 6-deoxy-l-allose with l-arabinose isomerase (TT-EaLAI) and l-ribose isomerase (TT-AcLRI), respectively, and then was epimerized to l-rhamnulose with immobilized d-tagatose 3-epimerase (IE-PcDTE). Following purification, l-rhamnulose was converted to 6-deoxy-l-glucose with d-arabinose isomerase (TT-BpDAI). The equilibrium ratios of 6-deoxy-l-psicose:6-deoxy-l-altrose, 6-deoxy-l-psicose:6-deoxy-l-allose, and l-rhamnulose:6-deoxy-l-glucose were 60:40, 40:60, and 27:73, respectively. The production yields of 6-deoxy-l-glucose, 6-deoxy-l-altrose, and 6-deoxy-l-allose from l-rhamnose were 5.4, 14.6, and 25.1%, respectively. These results indicate that the aldose isomerases used in this study acted on 6-deoxy aldohexoses.

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Section: Resultsmentioning

confidence: 99%

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confidence: 99%

Enzymatic production of three 6-deoxy-aldohexoses from l-rhamnose

Shompoosang

Yoshihara

Uechi

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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“…Examples hereof are terminusmodified fuculose analogues for L-fucose isomerase [21]. Other related enzymes, including xylose (glucose) isomerase, have also been shown to accept deoxygenated and/or substituted sugars [20,31,90]. It can thus be expected that several isomerases will be applied for the production of modified sugars in the near future.…”

Section: Isomerases For Deoxygenated and Other Modified Sugarsmentioning

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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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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“…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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A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose-3-epimerase—a reagent that is both specific and general

Cited by 25 publications

References 54 publications

Enzymatic production of three 6-deoxy-aldohexoses from l-rhamnose

Enzymatic production of three 6-deoxy-aldohexoses from l-rhamnose

Enzymes for the biocatalytic production of rare sugars

Advances in the enzymatic production of l-hexoses

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