First Synthesis of the α‐<scp>L</scp>‐Serine Linked Consensus Disaccharide of <i>Neisseria gonorrhoeae</i> and <i>Neisseria meningitidis</i>

Jana, Santanu; Emmadi, Madhu; Kulkarni, Suvarn S.

doi:10.1002/ijch.201400152

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“…The orthogonally protected rare sugar and glycosamine building blocks have been used in the assembly of various conjugation-ready bacterial oligosaccharides, including a trisaccharide fragment of Neisseria meningitides glycopeptide, a pseudotrisaccharide of Bacillus cereus, and phosphorylated trisaccharide of Providencia alcalifaciens O22, as well as archaeal N -linked hexasaccharide (Figure ). − ,, The azide containing rare sugars were shown to be especially useful for selective metabolic glycan labeling in pathogenic bacteria . By extending their methodology, Kulkarni and co-workers transformed l -rhamnose and l -fucose into various bacterial, rare deoxy amino l -sugars .…”

Section: One-pot Protection Of Carbohydratesmentioning

confidence: 99%

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

et al. 2018

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Carbohydrates, which are ubiquitously distributed throughout the three domains of life, play significant roles in a variety of vital biological processes. Access to unique and homogeneous carbohydrate materials is important to understand their physical properties, biological functions, and disease-related features. It is difficult to isolate carbohydrates in acceptable purity and amounts from natural sources. Therefore, complex saccharides with well-defined structures are often most conviently accessed through chemical syntheses. Two major hurdles, regioselective protection and stereoselective glycosylation, are faced by carbohydrate chemists in synthesizing these highly complicated molecules. Over the past few years, there has been a radical change in tackling these problems and speeding up the synthesis of oligosaccharides. This is largely due to the development of one-pot protection, one-pot glycosylation, and one-pot protection-glycosylation protocols and streamlined approaches to orthogonally protected building blocks, including those from rare sugars, that can be used in glycan coupling. In addition, new automated strategies for oligosaccharide syntheses have been reported not only for program-controlled assembly on solid support but also by the stepwise glycosylation in solution phase. As a result, various sugar molecules with highly complex, large structures could be successfully synthesized. To summarize these recent advances, this review describes the methodologies for one-pot protection and their one-pot glycosylation into the complex glycans and the chronological developments associated with automated syntheses of oligosaccharides.

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Section: One-pot Protection Of Carbohydratesmentioning

confidence: 99%

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

et al. 2018

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First Synthesis of the α‐L‐Serine Linked Consensus Disaccharide of Neisseria gonorrhoeae and Neisseria meningitidis

Abstract: The first total synthesis of the α‐L‐serine linked consensus disaccharide of Neisseria gonorrhoeae and Neisseria meningitidis was carried out in six linear steps, with 20.6 % overall yield.

Cited by 1 publication

References 33 publications

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates

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