Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

Yoshihara, Akihide; Haraguchi, Satoshi; Gullapalli, Pushpakiran; Rao, D. Mohan; Morimoto, Kenji; Takata, Goro; Jones, Nigel A.; Jenkinson, Sarah F.; Wormald, Mark R.; Dwek, Raymond A.; Fleet, George W. J.; Izumori, Ken

doi:10.1016/j.tetasy.2008.02.013

Cited by 36 publications

(24 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…L-rhamnose is the only cheaply available deoxy-hexose, but it can be transformed into 1-and 6-deoxygenated D/L-psicose, D/L-fructose, and L-tagatose by Enterobacter aerogenes IK7 [28,29]. Alternatively, Enterobacter agglomerans 221e can be applied in the synthesis of 1-and 6-deoxy-D-tagatose from both enantiomers of fucose [122]. In these processes, the deoxy-sugar is first chemically hydrogenated towards the corresponding polyol, which then serves as substrate for the enzymatic oxidation.…”

Section: Oxidoreductasesmentioning

confidence: 99%

Enzymes for the biocatalytic production of rare sugars

Beerens

Desmet

Soetaert

2012

Journal of Industrial Microbiology and Biotechnology

168

109

View full text Add to dashboard Cite

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.

show abstract

Section: Oxidoreductasesmentioning

confidence: 99%

Enzymes for the biocatalytic production of rare sugars

Beerens

Desmet

Soetaert

2012

Journal of Industrial Microbiology and Biotechnology

168

109

View full text Add to dashboard Cite

show abstract

“…The enzyme galactitol dehydrogenase (galactitol:NAD + 5 oxidoreductase; GatDH), originally isolated from a galactitol utilizing mutant of the bacterium Rhodobacter sphaeroides Si4, is a homotetrameric protein of 110,000 Da (D) that catalyzes the interconversion of galactitol into l-tagatose by using NAD + /NADH as the cofactor (Huwig et al, 1998). l-tagatose is a rare sugar with a promising precursor for the synthesis of high value added complex materials as illustrated by the facile and high yield preparation of the corresponding 1,2,3,4-diisopropylidene tagatofuranose (Yoshihara et al, 2008). In addition, GatDH oxidizes a variety of polyvalent aliphatic alcohols and polyols to the corresponding ketones and ketoses, respectively, and in the reverse reaction it reduces ketones with high stereoselectivity in turn yielding the corresponding (S)-configured alcohols (Kohring et al, 2003;Schneider et al, 1995).…”

Section: Introductionmentioning

confidence: 99%

Selective oxidation and reduction reactions with cofactor regeneration mediated by galactitol-, lactate-, and formate dehydrogenases immobilized on magnetic nanoparticles

Demir

Talpur

Sopacı

et al. 2011

Journal of Biotechnology

View full text Add to dashboard Cite

“…[29,30] Alternatively, biosynthetic transformationsw ith the aid of enzymes can also deoxygenate sugars. [31] Serving as the starting materials in this newly developed transformation, amino sugarsa re popularc ompounds. They occur widely in nature and are found in ag reat variety of polysaccharides, glycolipids, mucoproteins,n ucleotides,t eichoic acids, and antibiotics.…”

mentioning

confidence: 99%

Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction

et al. 2017

View full text Add to dashboard Cite

Benzyne was developed as a reducing agent in the key step of converting amino sugars and ketoses into deoxy sugars, which occur widely in natural products. Many deoxy sugars exhibit antibiotic and anticancer activities, and furthermore, they play essential biological roles. By treatment with CS2 and then Ac2O, amino sugars and ketoses were converted into the corresponding 1,3‐thiazolidine‐2‐thiones. In the key step, these intermediates were treated with 2‐trimethylsilylphenyl triflate (2.0 equiv.) and CsF (3.0 equiv.) in MeCN at 25 °C to produce acyclic enol acetates in 60–63 % yields. Saponification of the enol acetates with NaOMe/MeOH followed by intramolecular cyclization afforded the target 2‐deoxy sugars. The key step of the reductive deamination involved a domino 1,2‐elimination/[3+2]‐cycloaddition/retro [3+2]‐ring‐opening sequence. The generality of this new method was proven by the use of various substrates, including pentoses, hexoses, monosaccharides, disaccharides, aldoses, and ketoses.

show abstract

Isomerization of deoxyhexoses: green bioproduction of 1-deoxy-d-tagatose from l-fucose and of 6-deoxy-d-tagatose from d-fucose using Enterobacter agglomerans strain 221e

Cited by 36 publications

References 36 publications

Enzymes for the biocatalytic production of rare sugars

Enzymes for the biocatalytic production of rare sugars

Selective oxidation and reduction reactions with cofactor regeneration mediated by galactitol-, lactate-, and formate dehydrogenases immobilized on magnetic nanoparticles

Reductive Deamination by Benzyne for Deoxy Sugar Synthesis Through a Domino Reaction

Contact Info

Product

Resources

About