Glycosylation with activated sugars using glycosyltransferases and transglycosidases

Seibel, Jürgen; Jördening, Hans‐Joachim; Buchholz, Klaus

doi:10.1080/10242420600986811

Cited by 94 publications

(58 citation statements)

References 218 publications

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“…To synthesize polysaccharides by such repeated glycosylations, the in vitro approach by enzymatic catalysis has been significantly investigated because enzymes have remarkable catalytic advantages compared with other types of catalysts in terms of the stereo-and regioselectivities [9][10][11][12][13]. The enzymatic glycosylation is a very powerful tool for the stereo-and regioselective construction of the glycosidic linkages under mild conditions, where a glycosyl donor and a glycosyl acceptor can be employed in their unprotected forms, leading to the direct formation of an unprotected glycoside in aqueous media [14,15]. Thus, repetition of the enzymatic glycosylations, i.e., enzymatic polymerization, forms polysaccharides with well-defined structure.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Applications of Amylose Supramolecules by Means of Phosphorylase-Catalyzed Enzymatic Polymerization

Kadokawa

2012

Polymers

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This paper reviews preparation and applications of amylose supramolecules by means of phosphorylase-catalyzed enzymatic polymerization. When the enzymatic polymerization of α-D-glucose 1-phosphate (G-1-P) as a monomer was carried out in the presence of poly(tetrahydrofuran) (PTHF) of a hydrophobic polyether as a guest polymer, the supramolecule, i.e., an amylose-PTHF inclusion complex, was formed in the process of polymerization. Because the representation of propagation in the polymerization is similar to the way that vines of plants grow twining around rods, this polymerization method for the preparation of amylose-polymer inclusion complexes was proposed to be named -vine-twining polymerization‖. Various hydrophobic polyethers, polyesters, poly(ester-ether), and polycarbonates were also employed as the guest polymer in the vine-twining polymerization to produce the corresponding inclusion complexes. To obtain the inclusion complex from a strongly hydrophobic guest polymer, the parallel enzymatic polymerization system was developed as an advanced extension of the vine-twining polymerization. In addition, it was found that amylose selectively includes one side of the guest polymer from a mixture of two resemblant guest polymers, as well as a specific range in molecular weights of the guest PTHF. Amylose also exhibited selective inclusion behavior toward stereoisomers of poly(lactide)s. Moreover, the preparation of hydrogels through the formation of inclusion complexes of amylose in vine-twining polymerization was achieved.

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Section: Introductionmentioning

confidence: 99%

Preparation and Applications of Amylose Supramolecules by Means of Phosphorylase-Catalyzed Enzymatic Polymerization

Kadokawa

2012

Polymers

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“…One of the efficient methods to provide such a pure amylose is the enzymatic polymerization approach catalyzed by phosphorylase (EC 2.4.1.1) (Kobayashi and Makino 2009;Ziegast and Pfannemüller 1987). Phosphorylase is an enzyme that catalyzes the reversible phosphorolysis of α-(1 → 4)-glucans such as amylose at a non-reducing end in the presence of inorganic phosphate to produce α-D-glucose 1-phosphate (G-1-P) and those with one smaller degree of polymerization (DP) (Kitaoka and Hayashi 2002;Nakai et al 2013;Seibel et al 2006). Because the phosphorylase-catalyzed reaction exhibits reversibility, the enzyme also catalyzes the reversible reaction of the phosphorolysis, that is, a glucosylation using G-1-P as a glycosyl donor, to form α-(1 → 4)-glucosidic linkage with liberating inorganic phosphate.…”

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confidence: 99%

Hierarchically Fabrication of Amylosic Supramolecular Nanocomposites by Means of Inclusion Complexation in Phosphorylase-Catalyzed Enzymatic Polymerization Field

Kadokawa¹

2015

Advanced Structured Materials

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This chapter reviews hierarchically fabrication of eco-friendly supramolecular nanocomposites by means of inclusion complexation by amylose in phosphorylase-catalyzed enzymatic polymerization field. Amylose is a well-known polysaccharide and forms inclusion nanocomplex with various hydrophobic small molecules. A pure amylose is produced by the enzymatic polymerization using α-D-glucose 1-phosphate as a monomer and maltooligosaccharide as a primer catalyzed by phosphorylase. The author has found that a propagating chain of amylose in the enzymatic polymerization twines around hydrophobic polymers present in the reaction system to form inclusion nanocomplexes. The author named this polymerization system as 'vine-twining polymerization' because it is similar as the way that vine of plant grows twining around a rod. Amylosic supramolecular nanocomposite materials such as hydrogel and film were hierarchically fabricated by means of the vine-twining polymerization approach in the presence of copolymers covalently grafting with hydrophobic guest polymers. The enzymatically produced amyloses induced complexation with guest polymers in intermolecular graft copolymers, which acted as cross-linking points to form a supramolecular nanocomposite hydrogel. By using a film-formable main-chain in the graft copolymer, a supramolecular nanocomposite film was also obtained through hydrogelation. A supramolecular polymeric nanocomposite was successfully fabricated by the vine-twining polymerization using a primer-guest conjugate. The product in the vine-twining polymerization system formed a polymeric continuum of an inclusion nanocomplex, where the enzymatically produced amylose chain elongated from the conjugate included the guest segment in the other conjugate.

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“…Enzymes involved in the formation of glycosidic bonds are categorized into three main classes; hydrolytic enzymes (glycosyl hydrolases), phosphorolytic enzymes (phosphorylases), and glycosyl trasferases (15)(16)(17)(18).…”

mentioning

confidence: 99%

“…Phosphorylases catalyze phosphorolytic cleavage of glycosidic bonds at a non-reducing end in saccharide chains in the presence of inorganic phosphate to give the 1-phosphate of a monosaccharide (hexose 1-phosphate) and the saccharide chains with one smaller degree of polymerization (DP) (17,18). Because the bond energy of the produced phosphate is comparable with that of the glycosidic bond, the phosphorylase-catalyzed reactions exhibit reversible nature.…”

mentioning

confidence: 99%

Synthesis of Non-natural Oligosaccharides by ^|^alpha;-Glucan Phosphorylase-Catalyzed Enzymatic Glycosylations Using Analogue Substrates of ^|^alpha;-D-Glucose 1-Phosphate

Kadokawa

2013

TIGG

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Non-natural oligosaccharides can be expected to exhibit new functions and applications in glycoscience. Enzymatic glycosylation is a powerful tool for the preparation of oligosaccharides with well-defined structure. For example, α-(1 4)-glucosidic linkage can be constructed by α-glucan phosphorylase-catalyzed enzymatic glucosylation using α-D-glucose 1-phosphate (Glc-1-P) as a glycosyl donor. Because this enzyme expresses some loose specificity for recognition of substrate structures, the development of the α-glucan phosphorylase-catalyzed glycosylation using analogue substrates of Glc-1-P is the efficient approach to obtain new non-natural oligosaccharides. In this review, on the basis of above viewpoints, the facile synthesis of non-natural oligosaccharides by the α-glucan phosphorylase-catalyzed enzymatic glycosylations using such analogue substrates, i.e., hexose 1-phosphates as glycosyl donors is described. It has been found that α-D-

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Glycosylation with activated sugars using glycosyltransferases and transglycosidases

Cited by 94 publications

References 218 publications

Preparation and Applications of Amylose Supramolecules by Means of Phosphorylase-Catalyzed Enzymatic Polymerization

Preparation and Applications of Amylose Supramolecules by Means of Phosphorylase-Catalyzed Enzymatic Polymerization

Hierarchically Fabrication of Amylosic Supramolecular Nanocomposites by Means of Inclusion Complexation in Phosphorylase-Catalyzed Enzymatic Polymerization Field

Synthesis of Non-natural Oligosaccharides by ^|^alpha;-Glucan Phosphorylase-Catalyzed Enzymatic Glycosylations Using Analogue Substrates of ^|^alpha;-D-Glucose 1-Phosphate

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