Protonated Phenanthroline Catalyzed Stereoselective Glycosylation: Synthesis and Evaluation of Saponin Adjuvant Lablaboside F and Variants Leading to Simplified Vaccine Adjuvants.

ABSTRACT: Vaccine adjuvants are substances that are coadministered with antigens to enhance the immune response. Lablaboside F, a triterpene oleanolic acid β-linked to two trisaccharide chains on its eastern and western sides, emerged as a promising adjuvant candidate due to exhibiting robust adjuvanticity and low toxicity . We developed a β-stereoselective glycosylation method using a [PhenH]⁺[BF₄]^- catalyst to glycosylate oleanolic acid with C2-branched oligosaccharides, synthesizing lablaboside F and structural derivatives (S1-S8) as a result of constructing the target oligosaccharide. This approach simplifies the synthetic process when varying sugars are used and provides a platform for structure-activity relationship studies. Lablaboside F and S1-S8

SUBMITTER: Ghorai J 

PROVIDER: S-EPMC12728621 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature