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  • 1
    Electronic Resource
    Electronic Resource
    GGDEF and EAL domains inversely regulate cyclic di-GMP levels and transition from sessility to motility (2004)
    Oxford, UK : Blackwell Science Ltd
    Molecular microbiology 53 (2004), S. 0 
    Details
    ISSN: 1365-2958
    Source: Blackwell Publishing Journal Backfiles 1879-2005
    Topics: Biology , Medicine
    Notes: Cyclic nucleotides represent second messenger molecules in all kingdoms of life. In bacteria, mass sequencing of genomes detected the highly abundant protein domains GGDEF and EAL. We show here that the GGDEF and EAL domains are involved in the turnover of cyclic-di-GMP (c-di-GMP) in vivo whereby the GGDEF domain stimulates c-di-GMP production and the EAL domain c-di-GMP degradation. Thus, most probably, GGDEF domains function as c-di-GMP cyclase and EAL domains as phosphdiesterase. We further show that, in the pathogenic organism Salmonella enterica serovar Typhimurium, the nosocomial pathogen Pseudomonas aeruginosa and the commensal species Escherichia coli, GGDEF and EAL domains mediate similar phenotypic changes related to the transition between sessility and motility. Thus, the data suggest that c-di-GMP is a novel global second messenger in bacteria the metabolism of which is controlled by GGDEF and EAL domain proteins.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1111/j.1365-2958.2004.04206.x
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  • 2
    Electronic Resource
    Electronic Resource
    In vitro α1-3 or α1-4 fucosylation of type I and II oligosaccharides with secreted forms of recombinant human fucosyltransferases III and VI (1998)
    Springer
    Glycoconjugate journal 15 (1998), S. 873-883 
    Details
    ISSN: 1573-4986
    Keywords: Fucosyltransferase ; Lewis oligosaccharides ; mass spectrometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Transgalactosylation of chitobiose and chitotriose employing β-galactosidase from bovine testes yielded mixtures with β1-3 linked galactose (type I) and β1-4 linked galactose (type II) in a final ratio of 1:1 for the tri- and 1:1.4 for the tetrasaccharide. After 24 h incubations of the two purified oligosaccharide mixtures with large amounts (20-fold increase compared with standard conditions) of human α1, 3/4-fucosyltransferase III (FucT III), the type I tri-/tetrasaccharides were completely converted to the Lewisa structure, whereas approximately 10% fucosylation of the type II isomers to the Lewisx oligosaccharides was observed in long-term incubations. Employing large amounts of human α1, 3-fucosyltransferase VI (FucT VI), the type I trisaccharide substrate was exclusively fucosylated at the proximal O-4 substituted N-acetylglucosamine (GlcNAc) (20%) whereas almost all of the type II isomers was converted to the corresponding Lewisx product. 45% of the type I tetrasaccharide was fucosylated at the second GlcNAc solely by FucT VI. The type II isomer was almost completely α1-3 fucosylated to yield the Lewisx derivative with traces of a structure that contained an additional fucose at the reducing GlcNAc. The results obtained in the present study employing high amounts of enzyme confirmed our previous results that FucT III acts preponderantly as a α1-4 fucosyltransferase onto GlcNAc in vitro. Human FucT VI attaches fucose exclusively in an α1-3 linkage to 4-substituted GlcNAc in vitro and does not modify any 3-substituted GlcNAc to yield Lewisa oligosaccharides. With 8-methoxycarbonyloctyl glycoside acceptors used under standard conditions, FucT III acts exclusively on the type I and FucT VI only on the type II derivative. With lacto-N-tetraose, lacto-N-fucopentraose I, or LS-tetrasaccharide as substrates, FucT III modified the 3-substituted GlcNAc and the reducing glucose; FucT VI recognized only lacto-N-neotetraose as a substrate.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1006907031940
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  • 3
    Electronic Resource
    Electronic Resource
    Über die Reaktion von Phosphorigsäure-triäthylester mit β-Chlor-äthanolen (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 3963-3968 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Phosphorigsäure-triäthylester (1) bildet mit 1-Chlor-2-hydroxy-3-alkoxy-propanen 2 bei 120-150° in merklichem Ausmaß die entsprechenden β-Hydroxy-phosphonsäureester 3. Oberhalb 150° treten bevorzugt die Folgeprodukte einer Umesterung 1→4 auf. Neben höhermolekularen Verbindungen, die aus intermolekularen Reaktionen hervorgehen, entstehen u.a. cyclische Phosphonsäureester, so z.B. 1.3.2-Dioxaphospholane 8 und β-Phostone 11.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681011136
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  • 4
    Electronic Resource
    Electronic Resource
    Zur Reaktion von Aminonucleosiden mit Thiophosphorylierungsreagenzien (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 2152-2172 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Aminonucleosides with Thiophosphorylating ReagentsThe reactions of 3′-amino-3′-deoxyadenosine (1) and of some derivatives with thiophosphoryl chloride and with thionophosphoric acid chloridebis(p-nitrophenylester), respectively, is described together with the syntheses of the 3′-amido analogues 5 and 9 and the 3′,5′-diamido analogue 27 of adenosine 2′,3′- and 3′,5′-cyclothionophosphate, respectively, 5, 9 and 27 are formed as mixtures of diastereomers which are separated by chromatography. The reactions of the cAMP analogues and those of 3 and 23 with diazomethane is investigated. The structures of the new compounds are derived mainly from their 13C and 31P NMR spectra. The P—N bonds in 5 and 27 are less susceptible to acidolysis than they are in the corresponding compounds having P=O groups.
    Notes: Die Reaktion von 3′-Amino-3′-desoxyadenosin (1) und einiger Derivate mit Thiophosphorylchlorid bzw. mit Thionphosphorsäurechlorid-bis(p-nitrophenylester) sowie die Synthese der 3′-Amidoanalogen 5 und 9 und des 3′,5′-Diamidoanalogen 27 von Adenosin-2′,3′- bzw. -3′,5′- cyclothionphosphat werden beschrieben. 5, 9 und 27 fallen als Diastereomerengemische an, die chromatographisch getrennt werden. Die Umsetzung der cAMP-Analogen sowie die von 3 und 23 mit Diazomethan wird untersucht. Die Konstitution der neuen Verbindungen wird vor allem aus ihren 13C- und 31P-NMR-Spektren abgeleitet. Die P—N-Bindung in 5 und 27 ist acidolysebeständiger als in den entsprechenden Verbindungen mit P = O-Gruppierung.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110612
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  • 5
    Electronic Resource
    Electronic Resource
    Synthese der Cycloamide der xylo-3′-Amino-3′-desoxyadenosin-5′-phosphorsäure und -5′-thionophosphorsäure, zweier neuer cAMP-Analoga (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 3947-3949 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the Cycloamides of xylo-3′-Amino-3′-deoxyadenosine -5′-phosphoric Acid and -5′-thionophosphoric Acid, two New cAMP Analoguesxylo-3′-Amino-3′-deoxyadenosine (1) reacts with phosphoryl chloride or with thiophosphoryl chloride to yield the adenosine-3′,5′-cyclophosphates 3a or 3b, respectively, in high yields.
    Notes: No. Abstracts.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771101227
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  • 6
    Electronic Resource
    Electronic Resource
    Aminonucleoside, VIII. 3′-Amino-3′-desoxyadenosin,3,5′-Diamino-3′,5′-didesoxyadenosin und N-substituierte Derivate (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 2815-2828 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Aminonucleosides, VIII. 3′-Amino-3′-deoxyadenosine, 3′,5′-Diamino-3′,5′-dideoxyadenosine and Their N-Substituted DerivativesNew 3′-N-alkyl, 3′-N-cycloalkyl and 3′-N-alkylaryl derivatives are described of 3′-amino-3′-deoxyadenosine (1) and of 3′,5′-diamino-3′,5′-dideoxyadenosine (9). Ten N-monosubstituted derivatives 3a - j and four N,N-disubstituted derivatives 4a - d were obtained by reacting 1 with aldehydes or ketones and NaBH4 in acetate buffer. Reaction of 3′-benzyl-amino-3′-deoxyadenosine with formaldehyde gave oxazolidine 4g. 3′-N,N-Dimethylamino-3′-deoxyadenosine 4a was selectively quaternised in trimethyl phosphate to yield the 3′-N,N,N-trimethylammonium salt 13. The structures of the new compounds were derived mainly from their 13C and 1H NMR and mass spectra.
    Notes: Es werden neue 3′-N-Alkyl-,3′-5′N-Cycloalkyl- und 3′-N-Alkylarylderivate des 3′-Amino-3′-desoxyadenosins (1) bzw. des 3′,5′-Diamino-3′,5′-didesoxyadenosins (9) beschrieben. Zehn monosubstituierte Derivate 3a-j und vier disubstituierte Derivate 4a-d wurden erhalten durch Reaktion von 1 mit Aldehyden bzw. Ketonen und Natriumborhydrid in Acetatpuffer. Durch Reaktion des 3′-Benzylamino-3′-desoxyadenosins mit Formaldehyd erhielt man das Oxazolidinderivat 4g. Das 3′-N,N-Dimethylamino-3′-desoxyadenosin 4a ließ sich in Trimethylphosphat selektiv zum quartären 3′-N,N,N-Trimethylammoniumsalz 13 umsetzen. Die Konstitution der neuen Verbindungen wird vor allem aus ihren 1H-, 13C-NMR- und Massenspektren abgeleitet.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120808
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  • 7
    Electronic Resource
    Electronic Resource
    Aminonucleoside, XI. Bis(trimethylammonio)-Derivate von Adenosin (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 575-584 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Aminonucleosides, XI. - Bis(trimethy ammonio) Derivatives of AdenosineA five-step reaction starting from the aminonucleosides 1a or 1b yields the bis(trimethylammonio) derivatives 3′-trimethylammonio-6-[3-(trimethylammonio)propylamino]-3′-deoxyadenosine (8a) and 5′-trimethylammonio-6-[2-(trimethylammonio)ethylamino]-5′-deoxyadenosine (8b), respectively. The new compounds are biologically active and have muscle relaxing properties.
    Notes: Ausgehend von den Aminonucleosiden 1a und 1b wird in einer Fünf-Stufen-Reaktion die Synthese der Bis(trimethylammonio)-Derivate 3′-Trimethylammonio-6-[-3-(trimethylammonio)propylamino]-3′-desoxyadenosin (8a) und 5′-Trimethylammonio-6-[2-(trimethylammonio)ethylamino]-5′-desoxy-adenosin (8b) beschrieben. Die neuen Verbindungen sind biologisch aktiv und besitzen muskel-relaxierende Eigenschaften.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830407
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  • 8
    Electronic Resource
    Electronic Resource
    (2R,4R,6R,8R)-2,4,6,8-Tetramethyldecan- und -undecansäure aus dem Bürzeldrüsenwachs der Hausgans, Anser a. f. domesticus: Isolierung, Synthese einiger Derivate sowie der rac-2,4,6,8-Tetramethyldecansäure (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 433-439 
    Details
    ISSN: 0170-2041
    Keywords: Fatty acids ; Anser a.f. domesticus ; Waxes ; Preen-gland ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (2R,4R,6R,8R)-2,4,6,8-Tetramethyldecanoic- and -undecanoic Acid of the Preen-gland Wax from the Domestic Goose, Anser a.f. domesticus: Isolation, Synthesis of Derivatives and of the rac-2,4,6,8-Tetramethyldecanoic AcidLarge quantities of (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanoic- and -undecanoic acid methyl ester (3 and 4) were obtained after transesterification and Spaltrohr® distillation of the preen-gland wax of the domestic goose. Hydrolysis with NaOH/dioxan afforded the acids 5 and 6. Reduction of 3 with LiAlH4 gave (2R,4R,6R,8R)-2,4,6,8-tetramethyldecanol (7). Esterification of 5 and 6 with octadecanol yielded the pure wax esters 1 and 2, while 5 with glycerol gave the triglyceride 9 and 5 with 7 afforded 8. Alcohol 7 and octadecyl bromide, in the presence of NaH/DMF, afforded the ether 10. The racemic acid 22, corresponding to 5, was obtained synthetically by starting with a modified Wittig reaction of 2-(diethoxyphosphoryl)propionic acid ethyl ester on 2-methylbutyraldehyde. Transesterification of the ethyl ester 21 with octadecanol gave the racemic wax ester 23, corresponding to 1. The optical activity and 13C data of the compounds are reported.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199219920179
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  • 9
    Electronic Resource
    Electronic Resource
    Basenhydrierte Phosphonsäure-Derivate von Pyrimidinnucleosiden, Nebenprodukte bei der Desoxygenierung von 2′-O-Phenoxythiocarbonyl-Vorstufen (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1205-1210 
    Details
    ISSN: 0170-2041
    Keywords: Nucleotides, phosphonate analogs of ; Cytidine phosphonate, base hydrogenation of ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Base-Hydrogenated Phosphonic Acid Derivatives of Pyrimidine Nucleosides, Side Products in the Deoxygenation of 2′-O-Phenoxythiocarbonyl PrecursorsPersilylation of N4-anisoyl-1-(5-O-benzoyl-3-deoxy-3-diethoxyphosphorylmethyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl)cytosine (1) with iodotrimethylsilane followed by a Barton-McCombie reaction with Bu3SnH/azobis(isobutyronitrile) and hydrolysis with Et3NH+ buffer furnishes, in a side reaction, the N4-anisoyl-O5′-benzoyl-3′-deoxy-3′-phosphonomethyl-3,4,5,6-tetrahydro-cytosine lactones 4a and 4b, which are epimers at C-4 and can be separated by chromatography. Two-step hydrolysis of 4a and/or 4b yields an epimeric mixture of 1-(3-deoxy-3-phosphonomethyl-β-D-ribofuranosyl)-3,4,5,6-tetrahydro-uracil (6a/6b). A possible mechanism of the formation of 4a/4b from 1 via persilylated 2,2′-anhydro-N4-anisoyl-(5-O-benzoyl-3-deoxy-3-diethoxyphosphoryl-β-D-arabinofuranosyl)cytosine (9) as well as the reactivity of 9 and the behaviour of methyl 5-O-benzoyl-3-deoxy-3-diethoxyphosphoryl-2-O-phenoxythiocarbonyl-β-D-erythro-pentofuranoside (17) under the same reaction conditions are discussed. The structures of all new compounds are confirmed by their 1H-, 13C-, 31P-NMR and FAB mass spectra.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301195
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  • 10
    Electronic Resource
    Electronic Resource
    Aminonucleoside, X. Über die Synthese von 3′-Amino-3′-desoxyguanosin, 3′-Amino-3′-desoxyguanosin-5′-monophosphat und seinem 3′,5′-Cyclophosphat (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 666-674 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Aminonucleosides, X1). - Synthesis of 3′-Amino-3′-deoxyguanosine, 3′-Amino-3′-deoxyguanosine 5′-Monophosphate, and its 3′,5′-CyclophosphateTrifluoroacetylation and acetylation of 3′-amino-3′-deoxyadenosine (1) followed by acetolysis gives 1,2,5-tri-O-acetyl-3-trifluoroacetamido-β-D-ribofuranose (4b) which reacts with N2-acetylguanine in acetonitrile in the presence of hexamethyldisilazane, trimethylchlorosilane, and potassium perfluorobutanesulfonate to give 3′-amino-3′-deoxyguanosine (6) in an overall yield of 60%. Compound 6 contains 25% β-anomer and 75% β-anomer. - By introduction of the tert-butyl-oxycarbonyl protective group into 6b followed by phosphorylation according to Yoshikawa and hydrolysis in order to remove the 3′-N-Boc protective group 3′-amino-3′-deoxyguanosine 5′-monophosphate (8) could be obtained in good yield. Cyclization of 8 with water-soluble carbodiimide (EDC) at pH 7.7 and 40°C gives the cyclophosphate 9 in 90% yield. The structures of the new compounds are derived mainly from their 1H-, 13C-, and 31P-NMR spectra.
    Notes: 3′-Amino-3′-desoxyadenosin (1) wird nach Trifluoracetylierung sowie Acetylierung und Acetolyse zu 1,2,5-Tri-O-acetyl-3-trifluoracetamido-β-D-ribofuranose (4b) gespalten. 4b reagiert mit N2-Acetylguanin in Acetonitril bei Gegenwart von Hexamethyldisilazan, Trimethylchlorsilan und Kalium-perfluorbutansulfonat in ca. 60proz. Ausbeute zu 3′-Amino-3′-desoxyguanosin (6) aus ca. 25% α- und 75% β-Anomerem. - Nach Einführung der tert-Butyloxycarbonyl-Schutzgruppe in 6b, anschließender Phosphorylierung nach Yoshikawa, Hydrolyse und Abspaltung der 3′-N-Boc-Schutzgruppe erhält man in guten Ausbeuten das 3′-Amino-3′-desoxyguanosin-5′-monophosphat (8). Cyclisierung von 8 mit wasserlöslichem Carbodiimid (EDC) bei pH 7.7 und 40°C führt zu 90% des Cyclophosphats 9. Die Strukturen der neu synthetisierten Verbindungen werden durch 1H-, 13C- und 31P-NMR-Spektren abgesichert.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820406
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