ArticleThe Journal of organic chemistry2008
Synthetic studies toward Mycobacterium tuberculosis sulfolipid-I.
Article in The Journal of organic chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers, 1 of them a synthesis that pooled it.
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Who cites it
13 citing papers in PubMed, 1 synthesis or guideline pooled it, 61 citations in OpenAlex.
- Performance of purified antigens for serodiagnosis of pulmonary tuberculosis: a meta-analysis.Clinical and vaccine immunology : CVI · 2009Pooled it
- Synthesis of Sucrose-Mimicking Disaccharide by Intramolecular Aglycone Delivery.Molecules (Basel, Switzerland) · 2024Article
- Structural basis for the development of potential inhibitors targeting FadD23 from Mycobacterium tuberculosis.Acta crystallographica. Section F, Structural biology communications · 2023Article
- Underestimated Manipulative Roles ofFrontiers in immunology · 2019Review
- CD1b Tetramers Identify T Cells that Recognize Natural and Synthetic Diacylated Sulfoglycolipids from Mycobacterium tuberculosis.Cell chemical biology · 2018Article
- Tailoring Trehalose for Biomedical and Biotechnological Applications.Pure and applied chemistry. Chimie pure et appliquee · 2017Article
- Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues.Journal of visualized experiments : JoVE · 2017Article
- Intramolecular glycosylation.Beilstein journal of organic chemistry · 2017Review
- Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.Chemical reviews · 2016Review
- Development of αGlcN(1↔1)αMan-based lipid A mimetics as a novel class of potent Toll-like receptor 4 agonists.Journal of medicinal chemistry · 2014Article
- Sulfolipid-1 biosynthesis restricts Mycobacterium tuberculosis growth in human macrophages.ACS chemical biology · 2012Article
- Elucidation and chemical modulation of sulfolipid-1 biosynthesis in Mycobacterium tuberculosis.The Journal of biological chemistry · 2012Article
- Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research.Nature chemistry · 2009Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
2 authors at 2 institutions in 1 country.
Funding
Abstract
Sulfolipid-I (SL-I) is an abundant metabolite found in the cell wall of Mycobacterium tuberculosis that is comprised of a trehalose 2-sulfate core modified with four fatty acyl substituents. The correlation of its abundance with the virulence of clinical isolates suggests a role for SL-I in pathogenesis, although its biological functions remain unknown. Here we describe the synthesis of a SL-I analogue bearing unnatural lipid substituents. A key feature of the synthesis was application of an intramolecular aglycon delivery reaction to join two differentially protected glucose monomers, one prepared with a novel alpha-selective glycosylation. The route developed for the model compound can be readily extended to the synthesis of native SL-I as well as additional analogues for use in the investigation of SL-I's functions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.