ArticleNature communications2015
Total synthesis of tetraacylated phosphatidylinositol hexamannoside and evaluation of its immunomodulatory activity.
Article in Nature communications, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
10 citing papers in PubMed, 31 citations in OpenAlex.
- Expedient Synthesis of Superarmed Glycosyl Donors via Oxidative Thioglycosidation of Glycals.Synthesis · 2024Article
- The advances in adjuvant therapy for tuberculosis with immunoregulatory compounds.Frontiers in microbiology · 2024Review
- Asymmetric Synthesis of Contact Sex Pheromone ofMolecules (Basel, Switzerland) · 2022Article
- Structural basis for safe and efficient energy conversion in a respiratory supercomplex.Nature communications · 2022Article
- Chemical Synthesis of Cell Wall Constituents ofChemical reviews · 2021Review
- The Research Progress in Immunotherapy of Tuberculosis.Frontiers in cellular and infection microbiology · 2021Review
- Diastereoselective desymmetric 1,2-cis-glycosylation of meso-diols via chirality transfer from a glycosyl donor.Nature communications · 2020Article
- Recent Advances in the Synthesis of Glycoconjugates for Vaccine Development.Molecules (Basel, Switzerland) · 2018Review
- Twenty Years of Mycobacterial Glycans: Furanosides and Beyond.Accounts of chemical research · 2016Article
- A versatile glycosylation strategyChemical science · 2016Article
Corrections and comments
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Authors and funding
6 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Tuberculosis, aggravated by drug-resistant strains and HIV co-infection of the causative agent Mycobacterium tuberculosis, is a global problem that affects millions of people. With essential immunoregulatory roles, phosphatidylinositol mannosides are among the cell-envelope components critical to the pathogenesis and survival of M. tuberculosis inside its host. Here we report the first synthesis of the highly complex tetraacylated phosphatidylinositol hexamannoside (Ac2PIM6), having stearic and tuberculostearic acids as lipid components. Our effort makes use of stereoelectronic and steric effects to control the regioselective and stereoselective outcomes and minimize the synthetic steps, particularly in the key desymmetrization and functionalization of myo-inositol. A short synthesis of tuberculostearic acid in six steps from the Roche ester is also described. Mice exposed to the synthesized Ac2PIM6 exhibit increased production of interleukin-4 and interferon-γ, and the corresponding adjuvant effect is shown by the induction of ovalbumin- and tetanus toxoid-specific antibodies.
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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.