1283579-00-9Relevant academic research and scientific papers
Rapid and efficient synthesis of α(1-2)mannobiosides
Reina, José J.,Di Maio, Antonio,Ramos-Soriano, Javier,Figueiredo, Rute C.,Rojo, Javier
, p. 2873 - 2882 (2016)
α(1,2)mannobiosides with different substituents at the reducing end have been synthesized by a common strategy using benzoyls as the permanent protecting groups and an acetyl as the orthogonal protecting group at position C2 of the glycosyl acceptor. The
Straightforward synthesis of Man9, the relevant epitope of the high-mannose oligosaccharide
Ramos-Soriano, Javier,De La Fuente, M. Carmen,De La Cruz, Noelia,Figueiredo, Rute C.,Rojo, Javier,Reina, José J.
, p. 8877 - 8882 (2017)
The high-mannose oligosaccharide (or its corresponding Man9 epitope) is the most abundant structure present in pathogen envelope glycoproteins. These glycans play a key role in the pathogenesis of several pathogens and also in the communication with the immune system. Understanding the mechanism of action of these glycans requires the access to pure and chemically well-defined structures in reasonable amounts. The synthesis of these complex branched oligosaccharides is not trivial and few syntheses are reported in the literature with several synthetic and purification steps and low overall yields. In this work, we described a very efficient synthetic alternative to access this relevant Man9 epitope in a very straightforward manner.
Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan
Cao, Benjamin,White, Jonathan M.,Williams, Spencer J.
, p. 369 - 377 (2011/06/19)
Mycobacterium tuberculosis, the causitive agent of tuberculosis (TB), possesses a complex cell wall containing mannose-rich glycophospholids termed phosphatidylinositol mannosides (PIMs), lipomannan (LM), and lipoarabinomannan (LAM). These glycophospholipids play important roles in cell wall function and host-pathogen interactions. Synthetic PIM/LM/LAM substructures are useful biochemical tools to delineate and dissect the fine details of mannose glycophospholipid biosynthesis and their interactions with host cells. We report the efficient synthesis of a series of azidooctyl di- and trimannosides possessing the following glycan structures: α-Man-1,6-α-Man, α-Man-1,6-α-Man-1,6-α-Man, α-Man-1,2-α-Man-1,6- α-Man and 2,6-di-(α-Man)-α-Man. The synthesis includes the use of non-benzyl protecting groups compatible with the azido group and preparation of the branched trisaccharide structure 2,6-di-(α-Man)-α-Man through a double glycosylation of a 3,4-butanediacetal-protected manno-side. The azidooctyl groups of these synthetic mannans were elaborated to fluorescent glycoconjugates and squaric ester derivatives useful for further conjugation studies.
