Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• group. Chemical structures of (A) a representative PIM, AcPIM5 and (B) a mannan fragment of LM from mycobacteria. Boxes denote the relationship of PIMs and LM to trisaccharide fragments synthesized in this study. Target di- and trisaccharide glycoconjugate fragments of PIMs and LM. ORTEP plot of single

A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH

• Thisbe K. Lindhorst,
• Kathrin Bruegge,
• Andreas Fuchs and
• Oliver Sperling

Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90

• the known CRD at the tip of FimH and the suggested second binding site, which is a more extended region on the protein (Figure 1). Docking using FlexX [22][23][24] recommended a spacer of 10 to 15 amino acids to ligate the two different carbohydrate ligand portions of a bivalent glycoconjugate. This

Synthesis of 6-PEtN-α-D-GalpNAc-(1–>6)-β-D-Galp-(1–>4)-β-D-GlcpNAc-(1–>3)-β-D-Galp-(1–>4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof

• Andreas Sundgren,
• Martina Lahmann and
• Stefan Oscarson

Beilstein J. Org. Chem. 2010, 6, 704–708, doi:10.3762/bjoc.6.80

• carbohydrate surface antigens in glycoconjugate vaccines can be considered and investigated. One such suggested structure from Haemophilus influenzae LPS is the phosphorylated pentasaccharide 6-PEtN-α-D-GalpNAc-(1→6)-β-D-Galp-(1→4)-β-D-GlcpNAc-(1→3)-β-D-Galp-(1→4)-β-D-Glcp. Results: Starting from a spacer

• proven to be highly effective [2]. These vaccines are glycoconjugate vaccines, based on capsular poly- or oligosaccharide structures, either native or synthetic [3][4], linked to a carrier protein. The lipopolysaccharide (LPS) of H. influenzae shows a huge structural variety and hence non-capsulated

• , i.e. the bacteria express common human carbohydrate structures on their surface that the host recognises as self-structures and do not produce antibodies against. Construction of a glycoconjugate vaccine against NTHi is thus quite complex. Carbohydrate structures that are both exposed on the surface

Synthesis of glycosylated β³-homo-threonine conjugates for mucin-like glycopeptide antigen analogues

• Florian Karch and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47

• amino acid tandem repeat sequence of MUC1 using sequential solid-phase glycopeptide synthesis, a first example of a mixed α/β-hybrid glycopeptide building block was obtained. The latter is of interest for the development of novel glycoconjugate mimics and model structures for anti-cancer vaccines with