Synthesis of a Lipomannan Component of the Cell‐Wall Complex of<i>Mycobacterium tuberculosis</i>Is Based on Paulsen's Concept of Donor/Acceptor “Match”

Jayaprakash, K. N.; Lu, Jun; Fraser‐Reid, Bert

doi:10.1002/anie.200500505

Cited by 71 publications

(30 citation statements)

References 45 publications

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“…Owing to the significance of ManLAM, the synthesis of ManLAM and arabinan fragments has been attempted over the last two decades. 19 – 27 , 44 A recent investigation by Guo's group verified the synthetic and immunological potential of protein conjugated ManLAM fragments. 28 However, far too little attention has been paid to synthesizing the large oligomers in ManLAM.…”

Section: Introductionmentioning

confidence: 97%

Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

2017

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Section: Introductionmentioning

confidence: 97%

Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

2017

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“…Among these are the impressive synthesis of a pseudo-dodecasaccharide related to the PI core (3, Figure 4) by Fraser-Reid and coworkers (27). This synthesis follows earlier work in this area by the van Boom group, which was the first to synthesize phosphoinositide fragments of LAM (28,29).…”

Section: Introductionmentioning

confidence: 92%

Studies toward the Development of Anti-Tuberculosis Vaccines Based on Mycobacterial Lipoarabinomannan

Kim

Zheng

et al. 2008

ACS Symposium Series

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“…Syntheses of fragments 57 and 58 were also described. The "strong proinflammatory and apoptosis-inducing activity" [92] of lipomannan prompted the synthesis of the lipomannan dodecasaccharide 59 containing a bis-stearoylated phosphatidyl-glycero moiety in addition to a third stearoyl group attached to a mannose residue [93]. While 59 lacks a linker for conjugation to protein carriers, it may shed light on the biological role of this domain, including its recognition by lipomannan-specific antibodies.…”

Section: Mycobacterium Tuberculosismentioning

confidence: 99%

Recent Developments in Synthetic Oligosaccharide-Based Bacterial Vaccines

Pozsgay¹

2008

CTMC

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Synthetic advances made possible chemical assembly of complex oligosaccharide fragments of polysaccharide domains on the surface of human pathogenic bacteria. These oligosaccharides may be recognized by antibodies raised against high molecular weight, native, polysaccharides. In addition to their antigenicity, synthetic oligosaccharides can also function as haptens in their protein conjugates that can elicit not only oligo- but also polysaccharide-specific IgG antibodies in animal models and in humans. A major milestone in the development of new generation vaccines was the demonstration that protein conjugates of synthetic fragments of the capsular polysaccharide of Haemophilus influenzae type b are as efficacious in preventing childhood meningitis and other diseases as is the corresponding licensed commercial vaccine containing the bacterial polysaccharide. The lessons learnt in this and other endeavors described herein are manifold. For example, they teach us about the significance of the oligosaccharide epitope size, the number of their copies per protein in the conjugate, the possible effect of the spacer on anti-saccharide immune response, and the proper choice of the carrier protein combined with the selection of the animal model. The H. influenzae b story also teaches us that that the synthetic approach can be commercially viable.

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Synthesis of a Lipomannan Component of the Cell‐Wall Complex ofMycobacterium tuberculosisIs Based on Paulsen's Concept of Donor/Acceptor “Match”

Cited by 71 publications

References 45 publications

Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

Expedient synthesis of the heneicosasaccharyl mannose capped arabinomannan of the Mycobacterium tuberculosis cellular envelope by glycosyl carbonate donors

Studies toward the Development of Anti-Tuberculosis Vaccines Based on Mycobacterial Lipoarabinomannan

Recent Developments in Synthetic Oligosaccharide-Based Bacterial Vaccines

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