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Enzymology and Protein Engineering

Synthesis of Fucosyl-N-Acetylglucosamine Disaccharides by Transfucosylation Using α-l-Fucosidases from Lactobacillus casei

Jes�s Rodr�guez-D�az, Rodrigo J. Carbajo, Antonio Pineda-Lucena, Vicente Monedero, Mar�a J. Yebra
Jes�s Rodr�guez-D�az
aLaboratorio de Bacterias L�cticas y Probi�ticos, Departamento de Biotecnolog�a de Alimentos, IATA-CSIC, Valencia, Spain
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Rodrigo J. Carbajo
bStructural Biochemistry Laboratory, Medicinal Chemistry Department, Centro de Investigaci�n Pr�ncipe Felipe, Valencia, Spain
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Antonio Pineda-Lucena
bStructural Biochemistry Laboratory, Medicinal Chemistry Department, Centro de Investigaci�n Pr�ncipe Felipe, Valencia, Spain
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Vicente Monedero
aLaboratorio de Bacterias L�cticas y Probi�ticos, Departamento de Biotecnolog�a de Alimentos, IATA-CSIC, Valencia, Spain
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Mar�a J. Yebra
aLaboratorio de Bacterias L�cticas y Probi�ticos, Departamento de Biotecnolog�a de Alimentos, IATA-CSIC, Valencia, Spain
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DOI: 10.1128/AEM.00229-13
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    Fig 1

    Stability of the α-l-fucosidases AlfB (●) and AlfC (○). The enzymes (10 μg/ml) were incubated in 100 mM sodium phosphate buffer at pH 7.0 and 42�C, and the residual activities were determined at different time intervals with 2 mM p-nitrophenyl α-l-fucopyranoside as the substrate. The initial activity was defined as 100%. The data presented are mean values from three replicate experiments. The errors bars represent the standard deviations.

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    Fig 2

    (A and B) Partial 1D 1H NMR spectra (600 MHz, 313 K) covering the anomeric region of commercial fucosyl-α-1,3-N-acetylglucosamine (Fuc-α-1,3-GlcNAc) (A) and the transfucosylation reaction with AlfB (B). (C) 1H, 13C-HSQC of Fuc-α-1,3-GlcNAc (red) and the reaction mixture (black).

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    Fig 3

    (A and B) Partial 1D 1H NMR spectra (600 MHz, 313 K) covering the anomeric region of commercial fucosyl-α-1,6-N-acetylglucosamine (Fuc-α-1,6-GlcNAc) (A) and the transfucosylation reaction with AlfC (B). (C) 1H, 13C-HSQC of Fuc-α-1,6-GlcNAc (red) and the reaction mixture (black).

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    Fig 4

    Time course of the substrate consumption and the product formation by transfucosylation catalyzed by α-l-fucosidases AlfB (A) and AlfC (B). ●, p-nitrophenyl-α-l-fucopyranoside; ◆, p-nitrophenol; ▼, l-fucose; ■, fucosyl-α-1,3-N-acetylglucosamine; □, fucosyl-α-1,6-N-acetylglucosamine. Data from a representative experiment are shown.

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    Transglycosylation and hydrolysis activities of AlfB and AlfC

    EnzymeTransglycosylation (μmol/min/mg protein)Hydrolysis (μmol/min/mg protein)Vtrans/Vhyda
    AlfB0.951.500.63
    AlfC12.792.634.86
    • ↵a Tranglycolylation/hydrolysis (Vtrans/Vhyd) ratios were calculated from the initials rates of formation of transglycosylation products over the initial rates of hydrolysis.

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Synthesis of Fucosyl-N-Acetylglucosamine Disaccharides by Transfucosylation Using α-l-Fucosidases from Lactobacillus casei
Jes�s Rodr�guez-D�az, Rodrigo J. Carbajo, Antonio Pineda-Lucena, Vicente Monedero, Mar�a J. Yebra
Applied and Environmental Microbiology May 2013, 79 (12) 3847-3850; DOI: 10.1128/AEM.00229-13

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Synthesis of Fucosyl-N-Acetylglucosamine Disaccharides by Transfucosylation Using α-l-Fucosidases from Lactobacillus casei
Jes�s Rodr�guez-D�az, Rodrigo J. Carbajo, Antonio Pineda-Lucena, Vicente Monedero, Mar�a J. Yebra
Applied and Environmental Microbiology May 2013, 79 (12) 3847-3850; DOI: 10.1128/AEM.00229-13
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