Total Synthesis of a Glycoglycerolipid from <i>Meiothermus taiwanensis</i> through a One‐Pot Glycosylation Reaction and Exploration of its Immunological Properties

Ghosh, Biswajit; Lai, Yen-Hsun; Shih, Yu-Yin; Pradhan, Tapan Kumar; Lin, Chun‐Chi; Mong, Kwok-Kong Tony

doi:10.1002/asia.201300933

Cited by 10 publications

(4 citation statements)

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“…An example in this review is the total synthesis of glycoglycerolipid isolate 101. 76 The target glycoglycerolipid contains two ester functions that can be hydrolysed under basic conditions. Such conditions are required in global deprotection if the protected glycoglycerolipid, i.e.…”

Section: Outlook and Conclusionmentioning

confidence: 99%

Modulating glycosylation with exogenous nucleophiles: an overview

et al. 2014

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Section: Outlook and Conclusionmentioning

confidence: 99%

Modulating glycosylation with exogenous nucleophiles: an overview

et al. 2014

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“…For example, Wu and co-workers achieved the one-pot synthesis of a tetrasaccharide glycosyl glycerol by using activation of a glycosyl phosphite over selenoglycoside . More recently, Mong’s group reported a one-pot synthesis of the same tetrasaccharide using a low concentration glycosylation of thiotolylglycosides …”

Section: Glycosylationmentioning

confidence: 99%

“…366 More recently, Mong's group reported a one-pot synthesis of the same tetrasaccharide using a low concentration glycosylation of thiotolylglycosides. 367 Wong and co-workers also synthesized the SSEA-4 hexasaccharide 207 in a one-pot manner using selective activation of glycosyl phosphates. 323 As shown in Scheme 40, the dibutyl sialyl phosphate 204 was coupled with the thioglycoside donor−acceptor 205 with TMSOTf as the activator to generate the corresponding α-sialyl thioglycoside, which upon sequential coupling with the acceptor 206 in the presence of NIS in the same pot afforded the SESA-4 207 in 78% yield.…”

Section: Chemical Reviewsmentioning

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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“…Isopropylidene deprotection of 79 was then carried out using acetic acid and water In summary, the total synthesis of αGlc-DAGs 73a-d was achieved in seven steps and in 44-47% overall yields. Several other α-glycosylation methodologies have been reported for the synthesis of αGlc-DAGs, 102,[193][194][195][196][197] though of compounds 73a-d, only αGlc-DAG 73d has previously been synthesised, as noted by van Boom and co-workers in 9 steps and 27% overall yield. 198 Here,…”

Section: Synthesis Of αGlc-dags 73a-dmentioning

confidence: 99%

The Synthesis and Biological Evaluation of Ligands for C-Type Lectin Receptors

Khan¹

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<p>Macrophage inducible C-type lectin (Mincle), expressed on antigen presenting cells (APCs), is an important player in innate immunity due to its capacity to recognise pathogen-associated molecular patterns (PAMPs) and damage-associated molecular patterns (DAMPs), which are involved in pathogen recognition and in tissue homeostasis, respectively. Several ligands can bind Mincle and activate APCs to generate an inflammatory immune response, with prominent examples including the mycobacterial glycolipid, trehalose dimycolate (TDM), and the synthetic analogue thereof, trehalose dibehenate (TDB). Trehalose glycolipids exhibit anti-tumour properties and an ability to switch the phenotype of macrophages from one that is tumour promoting to one that is tumour suppressive. Insomuch, Mincle ligands have potential as adjuvants for both prophylactic and therapeutic (e.g. cancer) vaccines. Maradolipids, which were originally extracted from the nematode Caenorhabditis elegans, are glycolipids containing trehalose with symmetrical or asymmetrical iso-branched and straight chain fatty acids. The incorporation of the iso-branch makes them distinct from linear trehalose diesters (TDEs) and might provide the compounds with enhanced immunomodulatory properties. </p>

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Total Synthesis of a Glycoglycerolipid from Meiothermus taiwanensis through a One‐Pot Glycosylation Reaction and Exploration of its Immunological Properties

Cited by 10 publications

References 45 publications

Modulating glycosylation with exogenous nucleophiles: an overview

Modulating glycosylation with exogenous nucleophiles: an overview

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

The Synthesis and Biological Evaluation of Ligands for C-Type Lectin Receptors

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