Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase

Yamanoi, Takahiro; Yoshida, Naomichi; Oda, Yoshiki; Akaike, Eri; Tsutsumida, Maki; Kobayashi, Natsumi; Osumi, Kenji; Yamamoto, Kenji; Fujita, Kiyotaka; Takahashi, Keiko; Hattori, Kiyohiko

doi:10.1016/j.bmcl.2004.12.040

Cited by 37 publications

(15 citation statements)

References 22 publications

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“…47 Hattori and co-workers developed a chemoenzymatic approach for the preparation of monosubstituted CD derivatives that incorporated the sialoglycopeptide (SGP) branched oligosaccharide as a multivalent biorecognizable ligand (Scheme 3). 52 They first attached a unit of 4-hydroxyphenyl b-D-glucopyranoside (arbutin) at a single primary position onto bCD and then employed the endo-b-N-acetylglucosaminidase of Mucor hiemalis (Endo-M) and SGP from hen egg yolk to obtain the transglycosylation product. The presence of the arbutin moiety in the bCD acceptor warranted a high yield (65-67%) in the last step and, Scheme 1 Synthesis of monosubstituted divalent bCD conjugates according to Lancelon-Pin and Driguez.…”

Section: Cd-glycodendrimer Hybridsmentioning

confidence: 99%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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Section: Cd-glycodendrimer Hybridsmentioning

confidence: 99%

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

2013

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“…An interesting application of this enzymatic transglycosylation for synthesizing novel glycosylated cyclodextrin was recently reported 31. But enzymatic glycosylation of a broad range of natural products using this chemoenzymatic approach has not been investigated.…”

Section: Resultsmentioning

confidence: 99%

Introducing N-glycans into natural products through a chemoenzymatic approach

Huang¹,

Ochiai²,

Zhang³

et al. 2008

Carbohydrate Research

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The present study describes an efficient chemoenzymatic method for introducing a core N-glycan of glycoprotein origin into various lipophilic natural products. It was found that the endo-β-Nacetylglucosaminidase from Arthrobactor protophormiae (Endo-A) had broad substrate specificity and can accommodate a wide range of glucose (Glc)-or N-acetylglucosamine (GlcNAc)-containing natural products as acceptors for transglycosylation, when an N-glycan oxazoline was used as a donor substrate. Using lithocholic acid as a model compound, we have shown that introduction of an Nglycan could be achieved by a two-step approach: chemical glycosylation to introduce a monosaccharide (Glc or GlcNAc) as a handle, and then Endo-A catalyzed transglycosylation to accomplish the site-specific N-glycan attachment. For those natural products that already carry terminal Glc or GlcNAc residues, direct enzymatic transglycosylation using sugar oxazoline as the donor substrate was achievable to introduce an N-glycan. It was also demonstrated that simultaneous double glycosylation could be fulfilled when the natural product contains two Glc residues. This chemoenzymatic method is concise, site-specific, and highly convergent. Because N-glycans of glycoprotein origin can serve as ligands for diverse lectins and cell-surface receptors, introduction of a defined N-glycan into biologically significant natural products may bestow novel properties onto these natural products for drug discovery and development.

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“…These include monosaccharides (Gao et al, 2005b;Lu, Fraser-Reid, & Gowda, 2005;Dubber et al, 2006a;Dubber, Sperling, & Lindhorst, 2006), cyclodextrins (Carpenter & Nepogodiev, 2005;Furuike et al, 2005;Gómez-García et al, 2005;Hattori et al, 2006;Yamanoi et al, 2005), calix [4]arenes (48) (ten Cate et al, 2005;Hocquelet et al, 2006), carbosilanes , phthalocyanines (49) (Alvarez-Mico et al, 2006), poly(amidoamine) (PAMAM) (Ibey et al, 2005;Kubler-Kielb & Pozsgay, 2005;Mangold et al, 2005;Wolfenden & Cloninger, 2005;Wolfenden & Cloninger, 2006;Zhu & Marchant, 2006), peptides (Hada et al, 2005;Jin et al, 2006;Kantchev, Chang, & Chang, 2006;Sato, Hada, & Takeda, 2006), pentaerythritol (2/33) (Xue et al, 2005;Al-Mughaid & Grindley, 2006), porphyrins (50) (Laville et al, 2006;Sol et al, 2006), trihydroxybenzoic acid (51) (Fernandez-Megia et al, 2006;Joosten et al, 2006), and trimesic acid (4/61) .…”

Section: A Synthesis Of Multivalent Carbohydrates Dendrimers and Gmentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

Harvey

2010

Mass Spectrometry Reviews

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This review is the fourth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2006. The review covers fundamental studies, fragmentation of carbohydrate ions, method developments, and applications of the technique to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, glycated proteins, glycolipids from bacteria, glycosides, and various other natural products. There is a short section on the use of MALDI-TOF mass spectrometry for the study of enzymes involved in glycan processing, a section on industrial processes, particularly the development of biopharmaceuticals and a section on the use of MALDI-MS to monitor products of chemical synthesis of carbohydrates. Large carbohydrate-protein complexes and glycodendrimers are highlighted in this final section.

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Synthesis of mono-glucose-branched cyclodextrins with a high inclusion ability for doxorubicin and their efficient glycosylation using Mucor hiemalis endo-β-N-acetylglucosaminidase

Cited by 37 publications

References 22 publications

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Cyclodextrin-based multivalent glycodisplays: covalent and supramolecular conjugates to assess carbohydrate–protein interactions

Introducing N-glycans into natural products through a chemoenzymatic approach

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006

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