Convergent synthesis of a tetrasaccharide repeating unit of the O-specific polysaccharide from the cell wall lipopolysaccharide of Azospirillum brasilense strain Sp7

• Pintu Kumar Mandal,
• Debashis Dhara and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2014, 10, 293–299, doi:10.3762/bjoc.10.26

• and L-fucose [22]. Biological plant growth-promoting agents are becoming attractive as a means for the enhancement of the crop production while minimizing the hazards associated with the use of chemical fertilizers [23][24]. For a detailed understanding of the association of the LPS present in the

Multigramme synthesis and asymmetric dihydroxylation of a 4-fluorobut-2E-enoate

• James A. B. Laurenson,
• John A. Parkinson,
• Jonathan M. Percy,
• Giuseppe Rinaudo and
• Ricard Roig

Beilstein J. Org. Chem. 2013, 9, 2660–2668, doi:10.3762/bjoc.9.301

• -fucose (13, shown) and 6-deoxy-6-fluoro-D-galactose (Scheme 2) [13]. The main challenges we faced included the synthesis of 9 and its bromide precursor 8 in acceptable yield and purity, and the unexpectedly low regioselectivity of AD reactions of the fluorinated dienoate. Methyl sorbate (7) underwent AD

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• -gulose, L-galactose, L-fucose, allitol, D-talitol, and L-sorbitol. New systems and robust catalysts resulting from advancements in genomics and bioengineering are also discussed. Keywords: biosynthesis; enzyme; hexose; microorganism; rare sugars; Introduction Rare sugars are referred to as

• , and 5 [91]. L-Fucose (6-deoxy-L-galactose) L-Fucose is a rare sugar belonging to the deoxy sugar family, which is a naturally occurring sugar widely found in biomass, especially in plant, but in minor amounts. It is also found on the mammalian cell surface and a fundamental core moiety of various

• carbohydrate antigens [92][93]. Microbiological synthesis of L-fucose is based on the fermentation by microorganisms, which generate L-fucose-containing exopolysaccharides (EPS). Then, L-fucose can be released by enzymatic hydrolysis and recovered from the hydrolysate [94]. Interestingly, metabolically

Automated synthesis of sialylated oligosaccharides

• Davide Esposito,
• Mattan Hurevich,
• Bastien Castagner,
• Cheng-Chung Wang and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2012, 8, 1601–1609, doi:10.3762/bjoc.8.183

• hydroxy nucleophile on the central glucosamine. Our first attempt to glycosylate using fucose thioglycoside building block 25 afforded the product in low yield and as a mixture of anomers as confirmed by LC–MS analysis. The use of N-phenyl trifluoroacetimidate building block 24 proved more efficient

• . Nevertheless, when fucosylation with building block 24 was performed in dichloromethane, a mixture of anomers of compounds 26 was detected by NMR analysis. Only running the reaction in ether, which is a strong α-directing solvent [28], ensured stereoselective introduction of the fucose residue. Under these

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• β-subunit of human follicle-stimulating hormone (hFSH) glycoprotein was prepared, containing two complex type N-glycans, modified with core fucose and terminal sialic acid glycan residues [57]. The FSH β-subunit was prepared by sequential native chemical ligation. Initially, a larger C-terminal

• distance (Figure 2) [140][141][142]. In another study, a combinatorial library of fucosyl-peptide dendrimers was synthesized and screened for binding to the fucose-specific lectin (LecB) from Pseudomonas aeruginosa, a pathogen causing severe infections in patients leading to chronic inflammation in the

• L-fucose IC50 = 11 μM) [106]. The glycopeptide dendrimer was able to completely inhibit P. aeruginosa biofilm formation at a concentration of 50 μM and established biofilms from wild-type strain and clinical isolates could be completely dispersed. In a later study, analogues of FD2 49 were prepared

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

• siRNA inhibition of the fucosyltransferase FUT1 and GDP-4-keto-6-deoxymannose-epimerase/reductase (FX-protein) [19]. The FX-protein is required for de novo synthesis of GDP-fucose from GDP-mannose [46], whereas FUT 1 catalyzes the α2 fucosylation of blood group H type 1 and Lewisy oligosaccharides. The

• tubule formation. In our earlier study we reported that bis-glycosylated 3,4-bis(hydroxymethyl)furan derived saccharide mimetics containing fucose and galactose or two galactoses showed good structural agreements with the terminal oligosaccharides of Lewisy by in silico MD simulation, and at the same

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• , consistent with the molecular formula С75H118O39. GLC analysis of the acetylated (S)-2-octyl glycosides derived after full acid hydrolysis of compound 1 revealed the presence of D-galactose (D-Gal), L-arabinose (L-Ara), 6-deoxy-D-glucose (D-Qui), D-xylose (D-Xyl), L-rhamnose (L-Rha), D-fucose (D-Fuc), and D