- Modulating helicity through amphiphilicity - Tuning supramolecular interactions for the controlled assembly of perylenes
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Here we show that it is possible to modulate the supramolecular assembly of designed H-bonding amphiphilic perylene-based materials through simple solvent interactions. These modulated supramolecular interactions have been translated to and observed in macroscopic properties, and provide new pathways to the preparation of switchable interfaces based on designed supramolecular interactions.
- Huang, Yongwei,Hu, Jianchen,Kuang, Wenfeng,Wei, Zhixiang,Faul, Charl F. J.
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supporting information; experimental part
p. 5554 - 5556
(2011/06/23)
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- Squaric Acid Monoamide Mannosides as Ligands for the Bacterial Lectin FimH: Covalent Inhibition or Not?
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Bacteria use long proteinaceous appendages, called fimbriae or pili, to adhere to the surfaces of their host cells. Widely distributed among the Enterobacteriacae are type 1 fimbriae that mediate mannose-specific bacterial adhesion through the lectin FimH, located at the fimbrial tips. It is possible to design synthetic mannosides such that they show high affinity for FimH and can thus inhibit mannose-specific bacterial adhesion in a competitive manner. It has been found that mannosidic squaric acid monoamides serve especially well as inhibitors of type 1 fimbriae-mediated bacterial adhesion, but it has remained unclear whether this effect is due to specific inhibition of the bacterial lectin FimH or to unspecific bioconjugation between the lectin's carbohydrate binding site and a squaric acid monoamide. A bioconjugation reaction would result in a covalently crosslinked squaric acid diamide. Here it is shown that covalent inhibition of FimH by mannosidic squaric acid derivatives is very unlikely and that compounds of this type serve rather as excellent specific candidates for low-molecular-weight inhibitors of bacterial adhesion. This has been verified by testing the properties of glycosidic squaric acid monoamides in diamide formation, by two different adhesion assays with a series of selected control compounds, and by molecular docking studies that further support the results obtained in the bioassays. Candidates for specific antiadhesives: Squaric acid (SA) monoamides have the ability to crosslink unspecifically to amines. It has been shown that mannosidic SA monoamides serve as specific inhibitors of the bacterial lectin FimH and that no covalent bioconjugation within the lectin's carbohydrate binding site (CRD) occurs.
- Grabosch, Carsten,Hartmann, Mirja,Schmidt-Lassen, Joern,Lindhorst, Thisbe K.
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experimental part
p. 1066 - 1074
(2012/02/04)
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- Sugar-modified cytostatics
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The invention relates to cytostatics which, by modification with sugar, are tumor-specific. Suitable spacers ensure serum stability and at the same time an intracellular action.
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- New organogelators bearing both sugar and cholesterol units: An approach toward molecular design of universal gelators
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The gelators of organic solvents are classified into two categories on the basis of their basic intermolecular forces: hydrogen-bonded or nonhydrogen-bonded. To utilize these two interactions cooperatively for organogel formation we newly synthesized seven gelators (1-7) and two reference compounds (8 and 9) which have both a cholesterol moiety and a saccharide moiety within one molecule. The solubility of 1-7 changed drastically from totally insoluble one to very soluble one depending on the saccharide absolute configuration. In general, the gelator became very insoluble when it includes many equatorial OH groups, whereas it became very soluble when it includes many axial OH groups. Gelators 2 and 5 bearing two equatorial OH groups and one axial OH group acted as good gelators and in several cases the sol-gel phase-transition temperatures (measured in a sealed tube) were higher than the boiling points. The SEM observations of the xerogels established that the stable gels contain the entangled fibrous network. These results indicate that a very stable organogel can be designed by a cooperative coagulative effect of a cholesterol-cholesterol interaction and a saccharide-saccharide interaction.
- Amaike,Kobayashi,Shinkai
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p. 2553 - 2558
(2007/10/03)
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- Improvement of intestinal absorption of peptide drugs by glycosylation: Transport of tetrapeptide by the sodium ion-dependent D-glucose transporter
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A tetrapeptide (Gly-Gly-Tyr-Arg, GGYR), which is not transported by di- or tripeptide transporters, was glycosylated with p-(succinylamido)phenyl α- or β-D-glucopyranoside (α,β-SAPG) to investigate whether these glycosylated molecules are transported by t
- Nomoto, Masahiro,Yamada, Kazuhito,Haga, Makoto,Hayashi, Masahiro
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p. 326 - 332
(2007/10/03)
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- CHEMO-ENZYMATIC SYNTHESIS OF A GLYCOPOLYMER CARRYING CLUSTERED-N-ACETYL-Β-LACTOSAMINE MOIETIES
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A polyacrylamide derivative having a β-linked N-acetyllactosamine moiety, a major component of oligosaccharide chains of glycoproteins, on each repeating unit was synthesized via a chemo-enzymatic process. p-Nitrophenyl N-acetyl-β-lactosaminide was prepar
- Kobayashi, Kazukiyo,Kakishita, Naohito,Okada, Masahiko,Akaike, Toshihiro,Usui, Taichi
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p. 753 - 766
(2007/10/02)
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