Mechanism of chemical O-glycosylation: from early studies to recent discoveries

Mydock, Laurel K.; Demchenko, Alexei V.

doi:10.1039/b916088d

Cited by 246 publications

(152 citation statements)

References 122 publications

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“…Most methodologies developed for the assembly of complex oligosaccharide structures are aimed at investigating new, improved promoters to catalyze the glycosylation reaction [5] or more efficient coupling strategies such as: one-pot multistep glycosylation reactions, [6] polymer-supported, [7] fluorous tag [8] or ionic liquid-supported [9] oligosaccharide syntheses. However, little effort has been devoted to the development of efficient approaches that can be applied to the preparation of orthogonally protected monosaccharide building blocks.…”

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confidence: 99%

Copper(II) Triflate: A Versatile Catalyst for the One‐Pot Preparation of Orthogonally Protected Glycosides

et al. 2011

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The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the onepot preparation of orthogonal protected thio-and O-glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one-pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes.

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confidence: 99%

Copper(II) Triflate: A Versatile Catalyst for the One‐Pot Preparation of Orthogonally Protected Glycosides

et al. 2011

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“…The only method used for production of the pure amylose with the desired average molecular weight is a phosphorylase-catalyzed enzymatic polymerization [4]. Polysaccharides are theoretically produced by the repeated glycosylations of a glycosyl donor with a glycosyl acceptor to form a glycosidic linkage [5][6][7][8]. 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].…”

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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“…Since the new glycosidic linkage creates a new chirality center, particular care has to be taken with regards to the stereoselectivity. Although mechanistic studies of the glycosylation reaction are still scarce, certain conventions have already been established (20). Typical uncontrolled glycosylation leads to anomeric mixtures (mixtures of 1,2-cis/trans diastereomers).…”

Section: B the Development Of New Methods For Chemical Glycosylationmentioning

confidence: 99%

From Stereocontrolled Glycosylation to Expeditious Oligosaccharide Synthesis

Yasomanee

Demchenko

2013

TIGG

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Mechanism of chemical O-glycosylation: from early studies to recent discoveries

Abstract: The main focus of this perspective lies in the discussion of the recent mechanistic theories and supporting experimental evidences that have been put forth in an attempt to advance our understanding of the factors affecting chemical glycosylation.

Cited by 246 publications

References 122 publications

Copper(II) Triflate: A Versatile Catalyst for the One‐Pot Preparation of Orthogonally Protected Glycosides

Copper(II) Triflate: A Versatile Catalyst for the One‐Pot Preparation of Orthogonally Protected Glycosides

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

From Stereocontrolled Glycosylation to Expeditious Oligosaccharide Synthesis

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