Efficient one-pot enzymatic synthesis of alpha-(1 -> 4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase

Hiroyuki Nakai, Adiphol Dilokpimol, Maher Abou Hachem, Birte Svensson

    Research output: Contribution to journalJournal articleResearchpeer-review

    Abstract

    Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1 -> 4)-glucostdic disacchandes from maltose and five monosacchandes in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction Thus phosphorolysis of maltose to 0-glucose I -phosphate circumvented addition of costly 0-glucose 1-phosphate for reverse phosphorolysis with different monosacchande acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-a-glucopyranosyl-(1 4)-N-acetyl-a-glucosain inopyranose IN-acetyl-maltosamine I, alpha-b-glucopyranosyl( 1 -> 4)-o-glucosaminopyranose I maltosaminej, a-a-glucopyranosyl-(1 -> 4)-b-mannopyranose, alpha-n-glucopyranosyl-(1 -> 4)-t-fucopyranose and alpha-b-glucopyranosyl-(1 -> 4)-D-xylopyranose, respectively, from 0 1 M maltose, 0.5 M N-acetyl glucosamine, 0.1 M glucosamine. 0.1 M mannose, 1 M t-fucose and 0.5 M xylose in 02 M phosphate-citrate p1-I 62 These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosacchandes from low-cost disacchandes as catalysed by phosphorylases with different substrate specificities 2010 Elsevier Ltd All rights reserved.
    Original languageEnglish
    JournalCarbohydrate Research
    Volume345
    Issue number8
    Pages (from-to)1061-1064
    ISSN0008-6215
    DOIs
    Publication statusPublished - 2010

    Keywords

    • alpha-(1 -> 4)-Glucosidic disaccharides
    • Reverse phosphorolysis
    • Glycoside hydrolase family 65
    • beta-Glucose 1-phosphate
    • Phosphorolysis

    Cite this

    @article{cc05242a1e21415d872b819db655faa0,
    title = "Efficient one-pot enzymatic synthesis of alpha-(1 -> 4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase",
    abstract = "Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1 -> 4)-glucostdic disacchandes from maltose and five monosacchandes in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction Thus phosphorolysis of maltose to 0-glucose I -phosphate circumvented addition of costly 0-glucose 1-phosphate for reverse phosphorolysis with different monosacchande acceptors, resulting in 91{\%}, 89{\%}, 88{\%}, 86{\%} and 84{\%} yield of alpha-a-glucopyranosyl-(1 4)-N-acetyl-a-glucosain inopyranose IN-acetyl-maltosamine I, alpha-b-glucopyranosyl( 1 -> 4)-o-glucosaminopyranose I maltosaminej, a-a-glucopyranosyl-(1 -> 4)-b-mannopyranose, alpha-n-glucopyranosyl-(1 -> 4)-t-fucopyranose and alpha-b-glucopyranosyl-(1 -> 4)-D-xylopyranose, respectively, from 0 1 M maltose, 0.5 M N-acetyl glucosamine, 0.1 M glucosamine. 0.1 M mannose, 1 M t-fucose and 0.5 M xylose in 02 M phosphate-citrate p1-I 62 These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosacchandes from low-cost disacchandes as catalysed by phosphorylases with different substrate specificities 2010 Elsevier Ltd All rights reserved.",
    keywords = "alpha-(1 -> 4)-Glucosidic disaccharides, Reverse phosphorolysis, Glycoside hydrolase family 65, beta-Glucose 1-phosphate, Phosphorolysis",
    author = "Hiroyuki Nakai and Adiphol Dilokpimol and {Abou Hachem}, Maher and Birte Svensson",
    year = "2010",
    doi = "10.1016/j.carres.2010.03.021",
    language = "English",
    volume = "345",
    pages = "1061--1064",
    journal = "Carbohydrate Research",
    issn = "0008-6215",
    publisher = "Pergamon Press",
    number = "8",

    }

    Efficient one-pot enzymatic synthesis of alpha-(1 -> 4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase. / Nakai, Hiroyuki; Dilokpimol, Adiphol; Abou Hachem, Maher; Svensson, Birte.

    In: Carbohydrate Research, Vol. 345, No. 8, 2010, p. 1061-1064.

    Research output: Contribution to journalJournal articleResearchpeer-review

    TY - JOUR

    T1 - Efficient one-pot enzymatic synthesis of alpha-(1 -> 4)-glucosidic disaccharides through a coupled reaction catalysed by Lactobacillus acidophilus NCFM maltose phosphorylase

    AU - Nakai, Hiroyuki

    AU - Dilokpimol, Adiphol

    AU - Abou Hachem, Maher

    AU - Svensson, Birte

    PY - 2010

    Y1 - 2010

    N2 - Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1 -> 4)-glucostdic disacchandes from maltose and five monosacchandes in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction Thus phosphorolysis of maltose to 0-glucose I -phosphate circumvented addition of costly 0-glucose 1-phosphate for reverse phosphorolysis with different monosacchande acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-a-glucopyranosyl-(1 4)-N-acetyl-a-glucosain inopyranose IN-acetyl-maltosamine I, alpha-b-glucopyranosyl( 1 -> 4)-o-glucosaminopyranose I maltosaminej, a-a-glucopyranosyl-(1 -> 4)-b-mannopyranose, alpha-n-glucopyranosyl-(1 -> 4)-t-fucopyranose and alpha-b-glucopyranosyl-(1 -> 4)-D-xylopyranose, respectively, from 0 1 M maltose, 0.5 M N-acetyl glucosamine, 0.1 M glucosamine. 0.1 M mannose, 1 M t-fucose and 0.5 M xylose in 02 M phosphate-citrate p1-I 62 These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosacchandes from low-cost disacchandes as catalysed by phosphorylases with different substrate specificities 2010 Elsevier Ltd All rights reserved.

    AB - Lactobacillus acidophilus NCFM maltose phosphorylase (LaMalP) of glycoside hydrolase family 65 catalysed enzymatic synthesis of alpha-(1 -> 4)-glucostdic disacchandes from maltose and five monosacchandes in a coupled phosphorolysis/reverse phosphorolysis one-pot reaction Thus phosphorolysis of maltose to 0-glucose I -phosphate circumvented addition of costly 0-glucose 1-phosphate for reverse phosphorolysis with different monosacchande acceptors, resulting in 91%, 89%, 88%, 86% and 84% yield of alpha-a-glucopyranosyl-(1 4)-N-acetyl-a-glucosain inopyranose IN-acetyl-maltosamine I, alpha-b-glucopyranosyl( 1 -> 4)-o-glucosaminopyranose I maltosaminej, a-a-glucopyranosyl-(1 -> 4)-b-mannopyranose, alpha-n-glucopyranosyl-(1 -> 4)-t-fucopyranose and alpha-b-glucopyranosyl-(1 -> 4)-D-xylopyranose, respectively, from 0 1 M maltose, 0.5 M N-acetyl glucosamine, 0.1 M glucosamine. 0.1 M mannose, 1 M t-fucose and 0.5 M xylose in 02 M phosphate-citrate p1-I 62 These current yields of 0.27-0.34 g of disaccharide products from 10 mL reaction mixtures are easy to scale up and moreover the strategy can be applied to large-scale production of other oligosacchandes from low-cost disacchandes as catalysed by phosphorylases with different substrate specificities 2010 Elsevier Ltd All rights reserved.

    KW - alpha-(1 -> 4)-Glucosidic disaccharides

    KW - Reverse phosphorolysis

    KW - Glycoside hydrolase family 65

    KW - beta-Glucose 1-phosphate

    KW - Phosphorolysis

    U2 - 10.1016/j.carres.2010.03.021

    DO - 10.1016/j.carres.2010.03.021

    M3 - Journal article

    VL - 345

    SP - 1061

    EP - 1064

    JO - Carbohydrate Research

    JF - Carbohydrate Research

    SN - 0008-6215

    IS - 8

    ER -