Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

Zou, Wei; Brisson, Jean‐Robert; Larocque, Suzon; Gardner, Rebecca; Jennings, Harold J.

doi:10.1016/s0008-6215(99)00018-x

Cited by 6 publications

(3 citation statements)

References 20 publications

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“…These results showed that the pentasaccharide produced by the MR15 strain from Gb3 has the structure of Gb5. This identification was confirmed by the overall 1 H and 13 C NMR data that agreed closely with values previously published for 3-aminopropyl galactosylgloboside [23].…”

Section: Characterizationsupporting

confidence: 90%

Synthesis of globopentaose using a novel β1,3‐galactosyltransferase activity of the Haemophilus influenzae β1,3‐N‐acetylgalactosaminyltransferase LgtD

Randriantsoa¹,

Drouillard²,

Breton³

et al. 2007

FEBS Letters

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We have previously described a bacterial system for the conversion of globotriaose (Gb3) into globotetraose (Gb4) by a metabolically engineered Escherichia coli strain expressing the Haemophilus influenzae lgtD gene encoding b1,3-N-acetylgalactosaminyltransferase [Antoine, T., Bosso, C., Heyraud, A. Samain, E. (2005) Large scale in vivo synthesis of globotriose and globotetraose by high cell density culture of metabolically engineered Escherichia coli. Biochimie 87,[197][198][199][200][201][202][203]. Here, we found that LgtD has an additional b1,3-galactosyltransferase activity which allows our bacterial system to be extended to the synthesis of the carbohydrate portion of globopentaosylceramide (Galb-3GalNAcb-3Gala-4Galb-4Glc) which reacts with the monoclonal antibody defining the stage-specific embryonic antigen-3. In vitro assays confirmed that LgtD had both b1,3-GalT and b1,3-GalNAcT activities and showed that differences in the affinity for Gb3 and Gb4 explain the specific and exclusive formation of globopentaose.

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Section: Characterizationsupporting

confidence: 90%

Synthesis of globopentaose using a novel β1,3‐galactosyltransferase activity of the Haemophilus influenzae β1,3‐N‐acetylgalactosaminyltransferase LgtD

Randriantsoa¹,

Drouillard²,

Breton³

et al. 2007

FEBS Letters

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“…The chemical synthesis of globotetraose (25,43) and some of its derivatives (3,20,26) has been described previously. In these reactions, the saccharide building blocks must be selectively protected and then coupled and finally deprotected to obtain the desired stereochemistry and regiochemistry in the products.…”

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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“…Incomplete turnover in these reactions was unexpected because of the highly reactive nature of thioglycoside 3. 25 Indeed, a test glycosylation between 3 and monobenzyl ethylene glycol instead of thioether 4 with NIS/TfOH led to complete conversion (see ESI †). Thus, it is proposed that in these glycosylation reactions (Table 1, entries 3 and 4) the electrophilic iodonium species is in part sequestered by the alkyl benzylthioether moiety in 4, resulting in incomplete turnover.…”

Section: Development Of a Chemoselective Thioglycoside Activation Str...mentioning

confidence: 99%

Synthesis of conjugation-ready zwitterionic oligosaccharides by chemoselective thioglycoside activation

et al. 2014

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Synthesis and NMR assignments of galactosylgloboside and its β-d-GalNAc-(1→4)-α-d-Gal-linked positional isomer in a conjugatable form

Cited by 6 publications

References 20 publications

Synthesis of globopentaose using a novel β1,3‐galactosyltransferase activity of the Haemophilus influenzae β1,3‐N‐acetylgalactosaminyltransferase LgtD

Synthesis of globopentaose using a novel β1,3‐galactosyltransferase activity of the Haemophilus influenzae β1,3‐N‐acetylgalactosaminyltransferase LgtD

Donor Substrate Regeneration for Efficient Synthesis of Globotetraose and Isoglobotetraose

Synthesis of conjugation-ready zwitterionic oligosaccharides by chemoselective thioglycoside activation

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