Total Synthesis of <i>Mycobacterium tuberculosis</i> Dideoxymycobactin‐838 and Stereoisomers: Diverse CD1a‐Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition

Cheng, Janice M. H.; Liu, Ligong; Pellicci, Daniel G.; Reddiex, Scott J. J.; Cotton, Rachel N.; Cheng, Tan-Yun; Young, David C.; Rhijn, Ildiko Van; Moody, D. Branch; Rossjohn, Jamie; Fairlie, David P.; Godfrey, Dale I.; Williams, Spencer J.

doi:10.1002/chem.201605287

Cited by 14 publications

(8 citation statements)

References 31 publications

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“…An example is lipoarabinomannan, a major structural component of cell membrane of mycobacteria as well as an important virulence factor for Mtb (38). Responses against antigens of this class have been described for NKT cells (39)(40)(41)(42)(43).…”

Section: Natural Killer T Cellsmentioning

confidence: 99%

Innate and Adaptive Lymphocytes in Non-Tuberculous Mycobacteria Lung Disease: A Review

et al. 2022

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Non-tuberculous mycobacteria (NTM) are ubiquitous environmental microorganisms capable of a wide range of infections that primarily involve the lymphatic system and the lower respiratory tract. In recent years, cases of lung infection sustained by NTM have been steadily increasing, due mainly to the ageing of the population with underlying lung disease, the enlargement of the cohort of patients undergoing immunosuppressive medications and the improvement in microbiologic diagnostic techniques. However, only a small proportion of individuals at risk ultimately develop the disease due to reasons that are not fully understood. A better understanding of the pathophysiology of NTM pulmonary disease is the key to the development of better diagnostic tools and therapeutic targets for anti-mycobacterial therapy. In this review, we cover the various types of interactions between NTM and lymphoid effectors of innate and adaptive immunity. We also give a brief look into the mechanism of immune exhaustion, a phenomenon of immune dysfunction originally reported for chronic viral infections and cancer, but recently also observed in the setting of mycobacterial diseases. We try to set the scene to postulate that a better knowledge of immune exhaustion can play a crucial role in establishing prognostic/predictive factors and enabling a broader investigation of immune-modulatory drugs in the experimental treatment of NTM pulmonary disease.

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Section: Natural Killer T Cellsmentioning

confidence: 99%

Innate and Adaptive Lymphocytes in Non-Tuberculous Mycobacteria Lung Disease: A Review

et al. 2022

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“…A second total synthesis of DDM was reported in 2017 by the Williams group . Their synthesis was designed to optimize the synthesis by Young et al in terms of overall yield and potentially, undetected, epimerization during esterification or peptide coupling.…”

Section: Mycobactinsmentioning

confidence: 99%

Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis

2021

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The pathogen Mycobacterium tuberculosis (Mtb), causing tuberculosis disease, features an extraordinary thick cell envelope, rich in Mtb-specific lipids, glycolipids, and glycans. These cell wall components are often directly involved in host−pathogen interaction and recognition, intracellular survival, and virulence. For decades, these mycobacterial natural products have been of great interest for immunology and synthetic chemistry alike, due to their complex molecular structure and the biological functions arising from it. The synthesis of many of these constituents has been achieved and aided the elucidation of their function by utilizing the synthetic material to study Mtb immunology. This review summarizes the synthetic efforts of a quarter century of total synthesis and highlights how the synthesis layed the foundation for immunological studies as well as drove the field of organic synthesis and catalysis to efficiently access these complex natural products.

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“…CD1a-restricted T-cells can recognize Mtb-derived lipopeptide dideoxymycobactin (DDM). 128,129 CD1b-restricted T-cell responses have been defined mostly in the context of mycolic acid (MA), 130 glucose monomycolate (GMM), 121 sulfoglycolipids (SGLs, Mtb-specific), 131 and glycerol monomycolate (GroMM) 132…”

Section: Function Of Group 1 Cd1-restricted T-cells and Potential As Vaccine Targetsmentioning

confidence: 99%

The role of donor‐unrestricted T‐cells, innate lymphoid cells, and NK cells in anti‐mycobacterial immunity

Ruibal

Voogd

Joosten

et al. 2021

Immunological Reviews

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Total Synthesis of Mycobacterium tuberculosis Dideoxymycobactin‐838 and Stereoisomers: Diverse CD1a‐Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition

Cited by 14 publications

References 31 publications

Innate and Adaptive Lymphocytes in Non-Tuberculous Mycobacteria Lung Disease: A Review

Innate and Adaptive Lymphocytes in Non-Tuberculous Mycobacteria Lung Disease: A Review

Chemical Synthesis of Cell Wall Constituents of Mycobacterium tuberculosis

The role of donor‐unrestricted T‐cells, innate lymphoid cells, and NK cells in anti‐mycobacterial immunity

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