A cellulose-chitin hybrid polysaccharide having alternatingly β(1→4)-linked d-glucose (Glc) and N-acetyl-d-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazoline monomer of Glcβ(1→4)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitin hybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecular weight (M(n)) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer of GlcNAcβ(1→4)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzyme catalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselective manner. M(n) of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealed that these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnatural hybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils

structure, chemistry, human, polysaccharide, repeating unit, polysaccharides, X-ray diffraction, molecular, X-ray, crystalline, form, hybrids, sugar, enzymatic, enzyme, engineering, Japan, measurement, substrate, Bacillus, transition state, stereoselective, analogue, molecular weight, D-glucose, GLC, saccharide, hybrid, catalysis, cellulase, Biomolecular, polymerization, stereochemistry, lysozyme, neutrophil, Neutrophils, polycondensation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

365.335 g/mol (C₁₄H₂₃R₂NO₁₀, R = next and previous repeats, not counted in mol weight)

A cellulose-chitin hybrid polysaccharide having alternatingly β(1→4)-linked d-glucose (Glc) and N-acetyl-d-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazoline monomer of Glcβ(1→4)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitin hybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecular weight (M(n)) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer of GlcNAcβ(1→4)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzyme catalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselective manner. M(n) of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealed that these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnatural hybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils

structure, chemistry, human, polysaccharide, repeating unit, polysaccharides, X-ray diffraction, molecular, X-ray, crystalline, form, hybrids, sugar, enzymatic, enzyme, engineering, Japan, measurement, substrate, Bacillus, transition state, stereoselective, analogue, molecular weight, D-glucose, GLC, saccharide, hybrid, catalysis, cellulase, Biomolecular, polymerization, stereochemistry, lysozyme, neutrophil, Neutrophils, polycondensation

13C NMR data:
missing...
1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
4,2	Ac	-	2.04
4	bDGlcpN	4.55	3.68-3.73	3.64	3.64	3.68	3.64
	bDGlc?	5.23	3.48	3.73	3.54	3.48	3.64-3.91

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)N[C@H]1[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O

383.35 g/mol (C₁₄H₂₅NO₁₁)

A cellulose-chitin hybrid polysaccharide having alternatingly β(1→4)-linked d-glucose (Glc) and N-acetyl-d-glucosamine (GlcNAc) was synthesized via two modes of enzymatic polymerization. First, a sugar oxazoline monomer of Glcβ(1→4)GlcNAc (1) was designed as a transition-state analogue substrate (TSAS) monomer for chitinase catalysis. Monomer 1 was recognized by chitinase from Bacillus sp., giving rise to a cellulose-chitin hybrid polysaccharide (2) via ring-opening polyaddition with perfect regioselectivity and stereochemistry. Molecular weight (M(n)) of 2 reached 4030, which corresponds to 22 saccharide units. Second, a sugar fluoride monomer of GlcNAcβ(1→4)Glc (3) was synthesized for the catalysis of cellulase from Trichoderma viride. The enzyme catalyzed polycondensation of 3, providing a cellulose-chitin hybrid polysaccharide (4) in regio- and stereoselective manner. M(n) of 4 reached 2840, which corresponds to 16 saccharide units. X-ray diffraction measurements revealed that these hybrid polysaccharides did not form any characteristic crystalline structures. Furthermore, these unnatural hybrids of 2 and 4 were successfully digested by lysozyme from human neutrophils

structure, chemistry, human, polysaccharide, repeating unit, polysaccharides, X-ray diffraction, molecular, X-ray, crystalline, form, hybrids, sugar, enzymatic, enzyme, engineering, Japan, measurement, substrate, Bacillus, transition state, stereoselective, analogue, molecular weight, D-glucose, GLC, saccharide, hybrid, catalysis, cellulase, Biomolecular, polymerization, stereochemistry, lysozyme, neutrophil, Neutrophils, polycondensation

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

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

365.335 g/mol (C₁₄H₂₃R₂NO₁₀, R = next and previous repeats, not counted in mol weight)