Fucose and fucosylated oligosaccharides have important applications in various industries owing to their prebiotic, anti-inflammatory, anticoagulant, and antiviral activities. Here, we aimed to obtain fucosylated oligosaccharides using the acidolysis method to depolymerize exopolysaccharides extracted from Clavibacter michiganensis M1. Based on structural analysis, the prepared glucofucobiose was found to consist of D-glucose and L-fucose, with a molecular weight of 326 Da and a structure of D-Glcp-β-(1→4)-L-Fucp. The prebiotic activity of glucofucobiose was compared with that of 2'-fucosyllactose (2'-FL), the most abundant oligosaccharide in human milk. According to the results, glucofucobiose could significantly promote the proliferation of six probiotic strains, and short-chain fatty acid production of five probiotic strains on glucofucobiose was substantially higher than that on 2'-FL at 48 h of fermentation. Overall, this study proposed a new technology for obtaining fucosylated oligosaccharides. The prepared glucofucobiose was found to exhibit potential prebiotic activity and should be further assessed.

structure, Bacterial exopolysaccharides, 2'-Fucosyllactose, fucosylated oligosaccharide, glucofucobiose, prebiotic activity

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4	bDGlcp	104.719	74.977	77.035	71.105	77.504	62.174
	bLFucp	97.760	72.434	73.777	81.575	72.258	17.128


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4	bDGlcp	4.669	3.655	3.924	4.091	3.627	3.904-4.071
	bLFucp	4.780	3.631	3.813	4.160	4.057	1.517


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4	bDGlcp	104.719/4.669	74.977/3.655	77.035/3.924	71.105/4.091	77.504/3.627	62.174/3.904-4.071
	bLFucp	97.760/4.780	72.434/3.631	73.777/3.813	81.575/4.160	72.258/4.057	17.128/1.517

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 and fucosylated oligosaccharides have important applications in various industries owing to their prebiotic, anti-inflammatory, anticoagulant, and antiviral activities. Here, we aimed to obtain fucosylated oligosaccharides using the acidolysis method to depolymerize exopolysaccharides extracted from Clavibacter michiganensis M1. Based on structural analysis, the prepared glucofucobiose was found to consist of D-glucose and L-fucose, with a molecular weight of 326 Da and a structure of D-Glcp-β-(1→4)-L-Fucp. The prebiotic activity of glucofucobiose was compared with that of 2'-fucosyllactose (2'-FL), the most abundant oligosaccharide in human milk. According to the results, glucofucobiose could significantly promote the proliferation of six probiotic strains, and short-chain fatty acid production of five probiotic strains on glucofucobiose was substantially higher than that on 2'-FL at 48 h of fermentation. Overall, this study proposed a new technology for obtaining fucosylated oligosaccharides. The prepared glucofucobiose was found to exhibit potential prebiotic activity and should be further assessed.

structure, Bacterial exopolysaccharides, 2'-Fucosyllactose, fucosylated oligosaccharide, glucofucobiose, prebiotic activity

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4	bDGlcp	104.719	74.977	77.035	71.105	77.504	62.174
	aLFucp	93.817	70.146	70.407	77.010	68.014	17.058


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4	bDGlcp	4.669	3.655	3.924	4.091	3.627	3.904-4.071
	aLFucp	5.407	3.952	4.074	3.566	4.472	1.482


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
4	bDGlcp	104.719/4.669	74.977/3.655	77.035/3.924	71.105/4.091	77.504/3.627	62.174/3.904-4.071
	aLFucp	93.817/5.407	70.146/3.952	70.407/4.074	77.010/3.566	68.014/4.472	17.058/1.482

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)