Peptides presenting the binding site of human CD4 for the HIV-1 envelope glycoprotein gp120

• Julia Meier,
• Kristin Kassler,
• Heinrich Sticht and
• Jutta Eichler

Beilstein J. Org. Chem. 2012, 8, 1858–1866, doi:10.3762/bjoc.8.214

• underlying the protein function. Furthermore, such mimetic molecules are promising candidates for the inhibition of protein–protein interactions. Synthetic peptides can be produced as direct reproductions of protein fragments and by diverse chemical modification, including the integration of non

• transcriptase and integrase). During recent years, a range of structurally different CD4 mimetic molecules have been presented. These include small molecules [15][16][17][18] as well as stably folded miniproteins, which were mutated to present a putative binding site for gp120 [19][20][21]. We have recently

• presents the CDR2-like loop of CD4, is able to enhance binding of gp120 to the CD4i antibody mAb X5 [24] (Figure 4), providing further indication of a functional mimicry of CD4 by the mimetic peptides. Comformational stability of gp120-peptide complexes To investigate the conformational stability and

Design of a novel tryptophan-rich membrane-active antimicrobial peptide from the membrane-proximal region of the HIV glycoprotein, gp41

• Evan F. Haney,
• Leonard T. Nguyen,
• David J. Schibli and
• Hans J. Vogel

Beilstein J. Org. Chem. 2012, 8, 1172–1184, doi:10.3762/bjoc.8.130

• resonance (NMR) spectroscopy to determine the high-resolution structure in a membrane mimetic environment. The structure of gp41w was previously determined in the presence of DPC micelles [12]. However, when the three derivatives were tested with SDS and DPC micelles, the resulting NMR spectra were poorly

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

• -galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF), which is a bifunctional saccharide mimetic consisting of a bis-hydroxymethylated furan core, a galactose residue and a sulfate group. It represents a mimetic of the GAG-subunit and may interact with the cell-surface or the ECM. We report the

• incubation times. Inhibition of melanoma cell adhesion by a sulfated saccharide mimetic In order to investigate the potential of the synthesized saccharide mimetics to interfere with the binding of the human melanoma line WM-115 to ECM proteins, we used a standard adhesion assay. Cells were radioactively

• detectable carbohydrate–protein interaction, because the combined synthetic peptidic integrin ligands completely blocked cell adhesion to fibronectin, but on the other hand, cell adhesion could be inhibited with the sulfated saccharide mimetic GSF, probably by interfering with protein–protein interactions

Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors

• Davide Bini,
• Francesca Cardona,
• Matilde Forcella,
• Camilla Parmeggiani,
• Paolo Parenti,
• Francesco Nicotra and
• Laura Cipolla

Beilstein J. Org. Chem. 2012, 8, 514–521, doi:10.3762/bjoc.8.58

• inhibitors. It is worth noting that they have the nojirimycin ring in common with the trehalose mimetic compound 6 (Figure 1). Furthermore, it was also reported that pyrrolidine derivatives (i.e., DAB-1, 9, Figure 2) [19] may act as trehalase inhibitors, in particular as competitive inhibitors with affinity

(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

• interaction with a receptor [20]. As a consequence, a wide variety of methods to restrict the conformational freedom has been developed. One approach to get round this problem is the isosteric replacement of the amide bond in the peptide with a suitable mimetic to induce a specific secondary structure. Recent

Synthesis of novel photochromic pyrans via palladium- mediated reactions

• Christoph Böttcher,
• Gehad Zeyat,
• Saleh A. Ahmed,
• Elisabeth Irran,
• Thorben Cordes,
• Cord Elsner,
• Wolfgang Zinth and
• Karola Rueck-Braun

Beilstein J. Org. Chem. 2009, 5, No. 25, doi:10.3762/bjoc.5.25

• substitution pattern permits detailed nitrile and fluorine spectroscopic probing of the photochromism in solution and on surfaces over a broad temperature range. Furthermore, the closed form of the benzopyran-based ω-amino acid 6 (Scheme 2) might be an ideal photoswitchable β-turn mimetic. Optical stimulation

Synthesis and glycosidase inhibitory activity of new hexa- substituted C8-glycomimetics

• Olivia Andriuzzi,
• Christine Gravier-Pelletier,
• Gildas Bertho,
• Thierry Prangé and
• Yves Le Merrer

Beilstein J. Org. Chem. 2005, 1, No. 12, doi:10.1186/1860-5397-1-12

• led to the C8-voglibose mimetic 19 after purification by ion-exchange chromatography. The same sequence of reactions was uneventfully applied to the azido-alcohol 12 to afford the aminocyclitols 16 and 20. The new C8-carbasugars 5 and 6 and C8-aminocyclitols 15, 16, 19 and 20 have been assayed for