title: Novel process for producing 6-deoxy monosaccharides from l-fucose by coupling and sequential enzymatic method.
abstract: We biosynthesized 6-deoxy-L-talose, 6-deoxy-L-sorbose, 6-deoxy-L-gulose, and 6-deoxy-L-idose, which rarely exist in nature, from L-fucose by coupling and sequential enzymatic reactions. The first product, 6-deoxy-L-talose, was directly produced from L-fucose by the coupling reactions of immobilized D-arabinose isomerase and immobilized L-rhamnose isomerase. In one-pot reactions, the equilibrium ratio of L-fucose, L-fuculose, and 6-deoxy-L-talose was 80:9:11. In contrast, 6-deoxy-L-sorbose, 6-deoxy-L-gulose, and 6-deoxy-L-idose were produced from L-fucose by sequential enzymatic reactions. D-Arabinose isomerase converted L-fucose into L-fuculose with a ratio of 88:12. Purified L-fuculose was further epimerized into 6-deoxy-L-sorbose by D-allulose 3-epimerase with a ratio of 40:60. Finally, purified 6-deoxy-L-sorbose was isomerized into both 6-deoxy-L-gulose with an equilibrium ratio of 40:60 by L-ribose isomerase, and 6-deoxy-L-idose with an equilibrium ratio of 73:27 by D-glucose isomerase. Based on the amount of L-fucose used, the production yields of 6-deoxy-L-talose, 6-deoxy-L-sorbose, 6-deoxy-L-gulose, and 6-deoxy-L-idose were 7.1%, 14%, 2%, and 2.4%, respectively.
authors.affiliation: The United Graduate School of Agricultural Sciences, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan; Rare Sugar Research Center, Kagawa University, Miki, Kagawa 761-0795, Japan; Institute of Food Research and Product Development, Kasetsart University, Chatuchak, Bangkok 10900, Thailand.
authors.forename: Sirinan
authors.initials: S
authors.lastname: Shompoosang
authors.affiliation: Rare Sugar Research Center, Kagawa University, Miki, Kagawa 761-0795, Japan.
authors.forename: Akihide
authors.initials: A
authors.lastname: Yoshihara
authors.affiliation: The United Graduate School of Agricultural Sciences, Ehime University, 3-5-7 Tarumi, Matsuyama, Ehime 790-8566, Japan; Rare Sugar Research Center, Kagawa University, Miki, Kagawa 761-0795, Japan.
authors.forename: Keiko
authors.initials: K
authors.lastname: Uechi
authors.affiliation: Faculty of Agriculture, Kagawa University, Miki, Kagawa 761-0795, Japan.
authors.forename: Yasuhiko
authors.initials: Y
authors.lastname: Asada
authors.affiliation: Rare Sugar Research Center, Kagawa University, Miki, Kagawa 761-0795, Japan. Electronic address: morimoto@ag.kagawa-u.ac.jp.
authors.forename: Kenji
authors.initials: K
authors.lastname: Morimoto
mesh_terms: D019747:Aldose-Ketose Isomerases / Q000378:metabolism*; D002238:Carbohydrate Epimerases / Q000378:metabolism; D003837:Deoxy Sugars / Q000096:biosynthesis*; D005632:Fructose / Q000378:metabolism; D005643:Fucose / Q000378:metabolism*; D006601:Hexoses / Q000096:biosynthesis* / Q000378:metabolism; D009005:Monosaccharides / Q000096:biosynthesis*; D013013:Sorbose / Q000031:analogs & derivatives / Q000096:biosynthesis
chemical_list: C438083:6-deoxy-idose; D003837:Deoxy Sugars; D006601:Hexoses; D009005:Monosaccharides; C519898:fuculose; C003243:psicose; D005643:Fucose; D005632:Fructose; C011435:6-deoxy-gulose; C011754:6-deoxytalose; D002238:Carbohydrate Epimerases; D019747:Aldose-Ketose Isomerases; C062878:L-rhamnose isomerase; C022546:ribose isomerase; C019714:D-arabinose isomerase; C023298:xylose isomerase; D013013:Sorbose
keywords: 6-Deoxy-l-gulose; 6-Deoxy-l-idose; 6-Deoxy-l-sorbose; 6-Deoxy-l-talose; d-Allulose 3-epimerase; d-Arabinose isomerase; d-Glucose isomerase; l-Fucose; l-Rhamnose isomerase; l-Ribose isomerase