Fucose-containing oligosaccharides (FCOs) have important applications in the food, medicine, and cosmetics industries owing to their unique biological activities. The degradation of microbial fucose-containing exopolysaccharide (FcEPS) is a promising strategy for obtaining FCOs, and bacteriophage-borne glycanase is a useful tool for degrading FcEPS. Here, we aimed to obtain FCOs using bacteriophage-borne glycanase to depolymerize FcEPS from Enterobacter sakazakii. The FcEPS was mainly composed of l-fucose (42.72 %), d-galactose (20.59 %), and d-glucose (21.81 %). Based on the results of nuclear magnetic resonance and mass spectrometry, the obtained FCOs were disaccharide fragments with backbones of β-d-Glcp-(1→4)-β-l-Fucp and α-d-Galp-(1→3)-β-l-Fucp, respectively. So far, few studies of disaccharides prepared from FcEPS have been reported. This study demonstrated that the FcEPS of E. sakazakii was a reliable fucose-containing disaccharide source and that bacteriophage-borne glycanase was an effective degradation tool for obtaining FCOs fragments from FcEPS.

fucose, Enterobacter sakazakii, bacteriophage-borne glycanase, fucose-containing disaccharide, microbial exopolysaccharide

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4	bDGlcp	4.634	3.471	3.665	4.005	3.551	3.671-3.790
	bLFucp	4.532	3.472	3.541	3.787	3.905	1.377

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

326.298 g/mol (C₁₂H₂₂O₁₀)

Fucose-containing oligosaccharides (FCOs) have important applications in the food, medicine, and cosmetics industries owing to their unique biological activities. The degradation of microbial fucose-containing exopolysaccharide (FcEPS) is a promising strategy for obtaining FCOs, and bacteriophage-borne glycanase is a useful tool for degrading FcEPS. Here, we aimed to obtain FCOs using bacteriophage-borne glycanase to depolymerize FcEPS from Enterobacter sakazakii. The FcEPS was mainly composed of l-fucose (42.72 %), d-galactose (20.59 %), and d-glucose (21.81 %). Based on the results of nuclear magnetic resonance and mass spectrometry, the obtained FCOs were disaccharide fragments with backbones of β-d-Glcp-(1→4)-β-l-Fucp and α-d-Galp-(1→3)-β-l-Fucp, respectively. So far, few studies of disaccharides prepared from FcEPS have been reported. This study demonstrated that the FcEPS of E. sakazakii was a reliable fucose-containing disaccharide source and that bacteriophage-borne glycanase was an effective degradation tool for obtaining FCOs fragments from FcEPS.

fucose, Enterobacter sakazakii, bacteriophage-borne glycanase, fucose-containing disaccharide, microbial exopolysaccharide

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3	aDGalp	103.990	73.346	70.147	70.934	72.422	62.587
	bLFucp	94.321	70.488	77.929	71.546	68.410	17.250


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3	aDGalp	5.260	3.824	4.063	3.871	3.488	3.550-3.762
	bLFucp	4.324	3.778	3.487	3.667	3.837	1.331


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3	aDGalp	103.990/5.260	73.346/3.824	70.147/4.063	70.934/3.871	72.422/3.488	62.587/3.550-3.762
	bLFucp	94.321/4.324	70.488/3.778	77.929/3.487	71.546/3.667	68.410/3.837	17.250/1.331

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C[C@@H]1O[C@H](O)[C@@H](O)[C@H](O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H]1O

326.298 g/mol (C₁₂H₂₂O₁₀)

Periodate oxidation and Smith degradation, methylation analysis including uronic acid degradation, partial hydrolysis with acid, bacteriophage degradation, and p.m.r. spectroscopy have been used to elucidate the primary structure of the Klebsiella serotype-13 capsular polysaccharide. The polymer consists of pentasaccharide repeating-units comprising a 4)-β-D-Manp-(1 → 4)-α-D-Glcp-(1 → 3)-β-D-Glcp-(1 → chain with a 3,4-O-(1-carboxyethylidene)-β-D-Galp-(1 → 4)-α-D-GlcAp(1 → branch at position 3 of the mannose. It is shown that there is a glycanase activity associated with particles of Klebsiella bacteriophage No. 13. which catalyses hydrolysis of chain β-D-Glcp-(1 → 4)-β-D-Manp linkages in the type-13 polysaccharide. The chemical basis of some serological cross-reactions of the Klebsiella K13 antigen is discussed.

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

[*]O[C@H]1[C@H](O)[C@@H](CO)O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](CO)O[C@H]([*])[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O[C@H]2O[C@H](C(=O)O)[C@@H](O[C@@H]3O[C@H](CO)[C@@H]4O[C@@](C)(C(=O)O)O[C@@H]4[C@H]3O)[C@H](O)[C@H]2O)[C@@H]1O

894.735 g/mol (C₃₃H₅₀R₂O₂₈, R = next and previous repeats, not counted in mol weight)