ABSTRACT
Retraction of 'Chemical synthesis and antigenic activity of a phosphatidylinositol mannoside epitope from Mycobacterium tuberculosis' by Shi-Yuan Zhao et al., Chem. Commun., 2020, 56, 14067-14070, DOI: 10.1039/D0CC05573E.
ABSTRACT
Phosphatidylinositol mannosides (PIMs) have been investigated as lipidic antigens for a new subunit tuberculosis vaccine. A non-natural diacylated phosphatidylinositol mannoside (Ac2PIM2) was designed and synthesized by mimicking the natural PIM6 processing procedure in dentritic cells. This synthetic Ac2PIM2 was achieved from α-methyl d-glucopyranoside 1 in 17 steps in 2.5% overall yield. A key feature of the strategy was extending the use of the chiral myo-inositol building block A to the O-2 and O-6 positions of the inositol unit to allow for introducing the mannose building blocks B1 and B2, and to the O-1 position for the phosphoglycerol building block C. Building block A, being a flexible core unit, may facilitate future access to other higher-order PIM analogues. A preliminary antigenic study showed that the synthetic PIM epitope (Ac2PIM2) was significantly more active than natural Ac2PIM2, which indicated that the synthetic Ac2PIM2 can be strongly immunoactive and may be developed as a potential vaccine.
Subject(s)
Antigens/immunology , Epitopes/immunology , Mycobacterium tuberculosis/immunology , Phosphatidylinositols/immunology , Antigen-Antibody Reactions , Antigens/chemistry , Carbohydrate Conformation , Epitopes/chemistry , Mycobacterium tuberculosis/chemistry , Phosphatidylinositols/chemical synthesis , Phosphatidylinositols/chemistryABSTRACT
PGL-1 epitope 1 bearing a p-aminoethylphenol group was efficiently synthesized by using linear synthetic routes. A method for efficient synthesis of oligosaccharides containing rhamnose rings was developed. The chemistry is flexible and could be used for the synthesis of other PGLs antigens. A biotinylated PGL-1 antigen 23 was synthesized and could be used as a probe for early detection of leprosy.
