Bioorthogonal metabolic glycoengineering of human larynx carcinoma (HEp-2) cells targeting sialic acid

• Arne Homann,
• Riaz-ul Qamar,
• Sevnur Serim,
• Petra Dersch and
• Jürgen Seibel

Beilstein J. Org. Chem. 2010, 6, No. 24, doi:10.3762/bjoc.6.24

• , functionalized carbohydrates both in vitro and in vivo [2][3]. Acetylated monosaccharides, for example 2-azidoacetylamino-2-deoxy-1,3,4,6-tetraacetyl-β-D-glucopyranoside (Ac4GlcNAz, 16), are believed to permeate the cell membrane by diffusion processes [4]. Recently, it was reported that neuraminic acid

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

• José L. Jiménez Blanco,
• Fernando Ortega-Caballero,
• Carmen Ortiz Mellet and
• José M. García Fernández

Beilstein J. Org. Chem. 2010, 6, No. 20, doi:10.3762/bjoc.6.20

• resistant to nucleases [91][92] and the positive charge may give rise to cell membrane permeability through electrostatic attraction with the negatively charged groups of the proteoglycans at the cell surface. Using this strategy, Bruice and co-workers synthesised ribonucleic guanidine (RNG) and

Sordarin, an antifungal agent with a unique mode of action

• Huan Liang

Beilstein J. Org. Chem. 2008, 4, No. 31, doi:10.3762/bjoc.4.31

• fungi by stabilizing the ribosome/EF2 complex. This mode of action is in contrast to typical antifungals, which target the cell membrane. This unusual bioactivity makes sordarin a promising candidate for the development of new fungicidal agents, and provided the motivation for extensive research. Three

• integrity of the cell membrane through binding of ergosterol or inhibition of its biosynthesis [2][7], sordarin acts on elongation factor 2 (EF2). This enzyme catalyzes the translocation of the ribosome along mRNA during elongation of the emerging polypeptide chain [8]. Sordarin inhibits this translocation

Trifluoromethyl ethers – synthesis and properties of an unusual substituent

• Frédéric R. Leroux,
• Baptiste Manteau,
• Jean-Pierre Vors and
• Sergiy Pazenok

Beilstein J. Org. Chem. 2008, 4, No. 13, doi:10.3762/bjoc.4.13

• at the oxygen-adjacent position [71]. Conclusion In the life science field, single fluorine atoms, trifluoromethyl or trifluoromethoxy groups are used to tailor pKa values, to facilitate cell membrane penetration and to increase the metabolic stability of compounds. These features of fluorine

Stereoselective synthesis of (2S,3S,4Z)-4-fluoro- 1,3-dihydroxy- 2-(octadecanoylamino)octadec- 4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

• Gergana S. Nikolova and
• Günter Haufe

Beilstein J. Org. Chem. 2008, 4, No. 12, doi:10.3762/bjoc.4.12

• -position. While the primary OH group is functionalized with a carbohydrate, a phosphate, sulfate, etc. the 3-OH group is free for various interactions with other constituents of the cell membrane such as cholesterol or proteins [1][26]. The nature of these interactions among other factors depends on the

• configuration (2S,3S) of the products is controlled by the chiral auxiliary. In recent years several studies on cell membrane lipid models suggested that ceramide could act indirectly as a messenger by modulation of membrane properties. The membrane lipids (mostly sphingomyelin) together with cholesterol are

Colchitaxel, a coupled compound made from microtubule inhibitors colchicine and paclitaxel

• Karunananda Bombuwala,
• Thomas Kinstle,
• Vladimir Popik,
• Sonal O. Uppal,
• James B. Olesen,
• Jose Viña and
• Carol A. Heckman

Beilstein J. Org. Chem. 2006, 2, No. 13, doi:10.1186/1860-5397-2-13

• reactions are summarized in Scheme 2. Estimation of Partition Coefficients In order to estimate the extent to which colchitaxel may be able to permeate the cell membrane, logP values computed for the new compound were compared with those of the starting compounds. Its logP values were somewhat higher but