2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

• Hemali D. Premathilake and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2012, 8, 597–605, doi:10.3762/bjoc.8.66

• a more flexible approach for oligosaccharide synthesis. Concomitantly with our studies, Hung et al. came up with essentially the same idea and reported the synthesis of AP mannosides and their activation for O-mannosylation in the presence of ICl/AgOTf [27]. The following considerations driving our

Dependency of the regio- and stereoselectivity of intramolecular, ring-closing glycosylations upon the ring size

• Patrick Claude,
• Christian Lehmann and
• Thomas Ziegler

Beilstein J. Org. Chem. 2011, 7, 1609–1619, doi:10.3762/bjoc.7.189

• glycosylations. Schematic representation of the “prearranged-glycoside concept” for intramolecular, ring-closing glycosylation. Structures of compounds 1–5. Intramolecular glycosylation of peptide-tethered mannosides according to Fairbanks [38][39][40]. Isolated β(1→3)-glycosidic linkage favored by triad

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

• 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

• provided diacetate 19 in 60% yield. Compound 19 was converted into the trichloroacetimidate 16 following the approach of Kong and coworkers [38] or to the thioglycoside 17 by treatment with p-thiocresol and BF3·Et2O in toluene. Assembly of mannosides 1–4 Synthesis of the protected disaccharide 20 was

En route to photoaffinity labeling of the bacterial lectin FimH

• Thisbe K. Lindhorst,
• Michaela Märten,
• Andreas Fuchs and
• Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

• FimH that can complex α-D-mannosides. However, as the precise nature of the ligand–receptor interactions in mannose-specific adhesion is not yet fully understood, it is of interest to identify carbohydrate recognition domains on the fimbrial lectin also in solution. Photoaffinity labeling serves as an

• appropriate methodology in this endeavour and hence biotin-labeled photoactive mannosides were designed and synthesized for photoaffinity labeling of FimH. So far, the photo-crosslinking properties of the new photoactive mannosides could be detailed with the peptide angiotensin II and labeling of FimH was

• X-ray studies a carbohydrate recognition domain (CRD), which can complex one α-D-mannosyl residue, has been clearly identified [6][7][8]. However, other binding experiments performed with a multitude of synthetic as well as natural mannosides and oligomannosides are not in complete agreement with