Chemoenzymatic synthesis of dendritic sialyl Lewisx

Palcic, Monica M.; Li, Hong; Zanini, Diana; Bhella, Resham S.; Roy, René

doi:10.1016/s0008-6215(97)00263-2

Cited by 62 publications

(30 citation statements)

References 41 publications

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“…Biocatalytic approaches in which isolated enzymes, especially Leloir glycosyltransferases, are used are powerful and complementary alternatives to chemical synthesis of carbohydrates and glycoconjugates (18,19,27). So far, a large number of mammalian glycosyltransferases have been cloned and employed in oligosaccharide synthesis; these enzymes include bovine ␤-1,4-galactosyltransferase (7,24,28) and ␣-1,3-galactosyltransferase (7, 10) and human ␣-2,3-sialyltransferase (31), ␣-1,3-fucosyltransferase (2), and blood group A/B glycosyltransferases (32). However, the utility of these enzymes in large-scale synthesis of glycoconjugates is partially limited by the high cost of eukaryotic cell culture and by the low level of protein expression.…”

Section: Discussionmentioning

confidence: 99%

Donor Substrate Regeneration for Efficient Synthesis of Globotetraose and Isoglobotetraose

Shao

Zhang

Kowal

et al. 2002

Appl Environ Microbiol

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Here we describe the efficient synthesis of two oligosaccharide moieties of human glycosphingolipids, globotetraose (GalNAc␤133Gal␣134Gal␤134Glc) and isoglobotetraose (GalNAc␤133Gal␣133Gal␤13 4Glc), with in situ enzymatic regeneration of UDP-N-acetylgalactosamine (UDP-GalNAc). We demonstrate that the recombinant ␤-1,3-N-acetylgalactosaminyltransferase from Haemophilus influenzae strain Rd can transfer N-acetylgalactosamine to a wide range of acceptor substrates with a terminal galactose residue. The donor substrate UDP-GalNAc can be regenerated by a six-enzyme reaction cycle consisting of phosphoglucosamine mutase, UDP-N-acetylglucosamine pyrophosphorylase, phosphate acetyltransferase, pyruvate kinase, and inorganic pyrophosphatase from Escherichia coli, as well as UDP-N-acetylglucosamine C4 epimerase from Plesiomonas shigelloides. All these enzymes were overexpressed in E. coli with six-histidine tags and were purified by one-step nickel-nitrilotriacetic acid affinity chromatography. Multiple-enzyme synthesis of globotetraose or isoglobotetraose with the purified enzymes was achieved with relatively high yields.

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Section: Discussionmentioning

confidence: 99%

Donor Substrate Regeneration for Efficient Synthesis of Globotetraose and Isoglobotetraose

Shao

Zhang

Kowal

et al. 2002

Appl Environ Microbiol

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“…Very recently, we showed that a recombinant ppGalNAc-T1 allows the large-scale preparation of Tn-mucin glycoproteins [132]. Different groups have also combined series of glycosyltransferases in order to obtain complex oligosaccharidic structures [133][134][135][136].…”

Section: -In Vitro Enzymatic Methodsmentioning

confidence: 99%

Carbohydrate Antigens: Synthesis Aspects and Immunological Applications in Cancer

Freire¹,

Bay²,

Vichier-Guerre³

et al. 2006

MRMC

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“…[66] As an example, octameric sialyl Lewis X antigen, coupled on a dendritic poly(L-lysine) scaffold, was realized by the combination of solidphase peptide chemistry and chemoenzymatic glycosylation reactions. [67] In this context, the use of (solid-phase) combinatorial chemistry [59][60][61]68] was an indispensable tool to establish various glycopeptide dendrimer libraries exploring and strengthening, for example, of the binding affinity toward lectins. [69] The large interest in the realization of different dendritic scaffolds with various (oligo-)saccharide shells is motivated by the need to establish a better understanding of the structure/ activity relationship in glycodendrimers regarding the binding capacity of the biological binding unit/space in/ on proteins, viruses, bacteria, and cell surfaces.…”

Section: Thiol-ene 13-dipolar Cycloaddition and Others (Scheme 5)mentioning

confidence: 99%

Glycopolymers of Various Architectures—More than Mimicking Nature

Voit

Appelhans

2010

Macro Chemistry & Physics

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Carbohydrates have a highly important role in biological functions. The increasing understanding of their biological interactions has also triggered a strongly increased interest in the preparation of synthetic glycopolymers of various architectures and well‐defined structure which can mimic biological functions in a less complex environment. In the last few years synthetic approaches in polymer science have been refined and newly developed in order to achieve complex carbohydrate architectures and to make use of them in various areas like glycomics, biotechnology, biosensors, and medicine. Besides the use of especially controlled radical polymerization techniques, highly efficient polymer analogous reactions that can be carried out in aqueous media have been developed and applied to linear and dendritic macromolecules. Self assembly aspects and their effectiveness in biological functions have been assessed.

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Chemoenzymatic synthesis of dendritic sialyl Lewisx

Cited by 62 publications

References 41 publications

Donor Substrate Regeneration for Efficient Synthesis of Globotetraose and Isoglobotetraose

Donor Substrate Regeneration for Efficient Synthesis of Globotetraose and Isoglobotetraose

Carbohydrate Antigens: Synthesis Aspects and Immunological Applications in Cancer

Glycopolymers of Various Architectures—More than Mimicking Nature

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