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  • 1
    Electronic Resource
    Electronic Resource
    VI. Applications of S-layers (1997)
    Oxford, UK : Blackwell Publishing Ltd
    FEMS microbiology reviews 20 (1997), S. 0 
    Details
    ISSN: 1574-6976
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Biology
    Notes: The wealth of information existing on the general principle of S-layers has revealed a broad application potential. The most relevant features exploited in applied S-layer research are: (i) pores passing through S-layers show identical size and morphology and are in the range of ultrafiltration membranes; (ii) functional groups on the surface and in the pores are aligned in well-defined positions and orientations and accessible for binding functional molecules in very precise fashion; (iii) isolated S-layer subunits from many organisms are capable of recrystallizing as closed monolayers onto solid supports at the air-water interface, on lipid monolayers or onto the surface of liposomes. Particularly their repetitive physicochemical properties down to the subnanometer scale make S-layers unique structures for functionalization of surfaces and interfaces down to the ultimate resolution limit. The following review focuses on selected applications in biotechnology, diagnostics, vaccine development, biomimetic membranes, supramolecular engineering and nanotechnology. Despite progress in the characterization of S-layers and the exploitation of S-layers for the applications described in this chapter, it is clear that the field lags behind others (e.g. enzyme engineering) in applying recent advances in protein engineering. Genetic modification and targeted chemical modification would allow several possibilities including the manipulation of pore permeation properties, the introduction of switches to open and close the pores, and the covalent attachment to surfaces or other macromolecules through defined sites on the S-layer protein. The application of protein engineering to S-layers will require the development of straightforward expression systems, the development of simple assays for assembly and function that are suitable for the rapid screening of numerous mutants and the acquisition of structural information at atomic resolution. Attention should be given to these areas in the coming years.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1574-6976.1997.tb00306.x
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  • 2
    Electronic Resource
    Electronic Resource
    A Novel Approach to β-(1→4)-Linked Thiodisaccharides Starting from Disulfide Sugars (1999)
    Springer
    Monatshefte für Chemie 130 (1999), S. 1137-1145 
    Details
    ISSN: 1434-4475
    Keywords: Keywords. Disulfide sugars; Thiodisaccharides; Thioglycosides; Helferich glycosylation.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung.  Die Glykosidierung der Monosaccharide 4, 8 und 10, welche eine intramolekulare Disulfidbrücke besitzen, liefert unter Anwendung von Helferich-Bedingungen und einem Überschuß entsprechender Acetobromohexose 5 oder 11 als Donor regio- und stereospezifisch die 6-Thiocyanato-β-(1→4)-thiodisaccharide 6, 9 und 12 in guten Ausbeuten. Zusätzlich wurde, wenn auch in geringer Ausbeute, die Bildung der Trisaccharide 7 und 13 beobachtet. Dieser neue Syntheseweg zur Darstellung von thioglykosidischen Verknüpfungen öffnet einen Zugang zu einer Vielzahl an bioaktiven Disaccharid-Analoga.
    Notes: Summary.  Glycosylation of monosaccharides 4, 8, and 10 containing an intramolecular disulfide bridge by applying Helferich-conditions and an excess of acetobromohexose 5 or 11 as donor substrate yielded 6-thiocyanato-β-(1→4)-thiodisaccharides 6, 9, and 12 regio- and stereospecifically in moderate to good yields. In addition, the formation of trisaccharides 7 and 13 could be observed, albeit in low yield. This novel route for thioglycoside formation may open access to a variety of bioactive disaccharide analogues.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00010292
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  • 3
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, LIII Synthese von 3-Desoxy-D-manno-2-octulosonsäure-(KDO-)-haltigen Trisacchariden (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1288-1297 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LIII. - Synthesis of Trisaccharides Containing 3-Deoxy-D-manno-2-octulosonic Acid (KDO)The disaccharide 9 consisting of two glucosamine units reacts with the pyranosyl bromide of 3-deoxy-D-manno-2-octulosonic acid (KDO) 11 to give the KDO-containing trisaccharides 12 and 14 of which the α-glycosidically linked isomer 12 is the most preponderant product. In a series of deblocking steps the free trisaccharide α-KDO-(2→3)-β-D-GlcNAc-(1→6)-D-GlcNAc 18 could be obtained from 12. The assignment to the α-glycosidic linkage of the KDO unit in 12 has been established by converting 19 into the lactone 20.
    Notes: Durch Umsetzung des aus zwei Glucosamin-Einheiten bestehenden Disaccharides 9 mit dem Pyranosylbromid der 3-Desoxy-D-manno-2-octulosonsäure (KDO) 11 sind die KDO-haltigen Trisaccharide 12 und 14 zu erhalten, von denen das α-glycosidisch verknüpfte Produkt 12 sehr stark überwiegt. Durch eine Entblockierungssequenz ist aus 12 das freie Trisaccharid α-KDO-(2→3)-β-D-GlcNAc-(1→6)-D-GlcNAc 18 zu gewinne. Die Zuordnung zur α-glycosidischen Verknüpfung des KDO-Teiles in 12 erfolgte durch Überführung von 19 in das Lacton 20.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840704
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  • 4
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, LXXIX. Synthese der Sequenz α-KDO-(2 → 4)-α-KDO-(2 → 6)-D-GlcN der inneren Core-Struktur von Lipopolysacchariden (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 273-281 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LXXIX1). - Synthesis of the Sequence α-KDO-(2→4)-α-KDO-(2→6)-D-GlcN of the “Inner Core” Structure of LipopolysaccharidesThe glycosyl halide of 3-deoxy-D-manno-2-octulosonic acid (KDO) (5) reacts with the D-glucosamine derivative 4 to give the α-(2→6) glycosidically linked disaccharide 6. After deacetylation from 6 to 7 and conversion into the isopropylidene sugar 16, the disaccharide can be used for a subsequent glcoside synthesis. The coupling of 5 with 16 affords regioselectively the α-(2→4) linked trisaccharide 18. In a series of deblocking steps, α-KDO-(2→4)-α-KDO-(2→6)-D-GlcN (24) can be obtained, which is an important sequence of the “inner core” structure of the lipopolysaccharides.
    Notes: Das Glycosylhalogenid der 3-Desoxy-D-manno-2-octulosonsäure (KDO) (5) läßt sich mit dem D-Glucosamin-Derivat 4 zum α-(2→6)-glycosidisch verknüpften Disaccharid 6 umsetzen. Nach Entacetylierung von 6 zu 7 und Überführung in die Isopropylidenverbindung 16 kann das Disaccharid erneut für eine Glycosidsynthese eingesetzt werden. Die Umsetzung von 5 mit 16 ergibt regioselektiv das α-(2→4)-glycosidisch verknüpfte Trisaccharid 18. Durch eine Folge von Entblockierungsschritten ist hieraus α-KDO-(2→4)-α-KDO-(2→6)-D-GlcN (24) zu erhalten, das eine wichtige Sequenz der inneren Core-Struktur von Lipopolysacchariden darstellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870322
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  • 5
    Electronic Resource
    Electronic Resource
    Bausteine von Oligosacchariden, LII. Synthese von Disacchariden aus 3-Desoxy-D-manno-2-octulosonsäure (KDO) und D-Glucosamin (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1270-1287 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Building Units of Oligosaccharides, LII. - Synthesis of Disaccharides Containing 3-Deoxy-D-manno-2-octulosonic Acid (KDO) and D-GlucosamineThe pyranosyl bromide 2 of 3-deoxy-D-manno-2-octulosonic acid (KDO) can be coupled favourably with benzyl 2-benzyloxycarbonylamino-2-deoxy-4,6-O-ethyliden-α-D-glucopyranoside (7) which yields the (2→3)-glycosidically linked disaccharide containing KDO and D-glucosamine. Using mercury salts as catalysts it depends on the kind of solvent whether only the α-D-glycosidically bound product 10a or a mixture of the anomers will be obtained. After separation of the anomers and deblocking, the two disaccharides α-KDO-(1→3)-D-GlcNAc 21 and β-KDO-(2→3)-D-GlcNAc 26 have been prepared. The assignment of the anomeric configuration could be accomplished by NOE experiments and by conversion into the lactone 31.
    Notes: Das Pyranosylbromid 2 der 3-Desoxy-D-manno-2-octulosonsäure (KDO) läßt sich am günstigsten mit dem Benzyl-2-benzyloxycarbonylamino-2-desoxy-4,6-O-ethyliden-α-D-glucopyranosid (7) zu (2→3)-glycosidisch verknüpften Disacchariden aus KDO und D-Glucosamin umsetzen. Je nach Art des Lösungsmittels wird nur das α-D-glycosidisch verknüpfte Produkt 10a oder ein Gemisch der Anomeren erhalten. Quecksilbersalze dienen als Katalysatoren. Nach Trennung der Anomeren und Entblockierung wurden die beiden Disaccharide α-KDO-(2→3)-D-GlcNAc 21 und α-KDO-(2→3)-D-GlcNAc 26 dargestellt. Die Zuordnung der Anomerenkonfiguration erfolgte durch NOE-Experimente und durch Überführung in das Lacton 31.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840703
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