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  • Organic Chemistry  (35)
  • Cyclodextrins  (2)
  • 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane  (1)
  • 1
    ISSN: 1573-1561
    Keywords: Enantiomer discrimination ; male patrolling ; odor marking ; Hymenoptera ; Apoidea ; Andrena wilkella ; bee ; EAG ; spiroacetal ; absolute configuration ; 2,8-dimethyl-1,7-dioxaspiro[5.5]undecane
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Diastereomers of the spiroacetal, 2,8-dimethyl-1,7-dioxaspiro [5.5]undecane, represent main components of the cephalic secretion from males of the solitary bee,Andrena wilkella. The major compound proved to be of high enantiomeric purity, showing (2S,6R,8S) configuration. Only the naturally occurring enantiomer attracted patrolling males in the field; its antipode was behaviorally inactive and in a racemic mixture did not inhibit response. The (E,Z) diastereomers were also found to be almost inactive. EAG studies gave the same result as the behavioral tests. The biological function of the spiroacetal is discussed in view of the evolution of the mating behavior inA. wilkella.
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  • 2
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolites of Microorganisms, 171.  -  Ethericin A; Isolation, Characterization and Structure of a Novel Antibiotically Active Diphenyl EtherThe previously unknown antibiotic ethericin A has been isolated from cultures of Aspergillus funiculosus. It inhibits the growth of bacteria and some fungi. Ethericin A has been identified by mass spectrometry, NMR, chemical degradation and synthesis as 5,5'-dimethyl-3,3' -oxydipyrocatechol (3).
    Notes: Das bisher unbekannte, aus Aspergillus funiculosus isolierte Ethericin A hemmt das Wachstum von Bakterien und einigen Pilzen. Durch Massen- und Kernresonanzspektrometrie, chemischen Abbau sowie Synthese ist die Verbindung als 5,5'-Dimethyl-3,3'-oxydibrenzcatechin (3) identifiziert worden.
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  • 3
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1976 (1976), S. 2011-2020 
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Structure of the Peptide Antibiotic StenothricinThe structure of the peptide antibiotic Stenothricin was investigated by combined application of chromatography, degradation, derivatization, and mass spectrometry. Most probably Stenothricin is β-ketoacyl-D-Cys(O3H)-L-Val-D-Ser-L-Lys-Sar-D-αThr-L-Ser-L-diaminopropionic acid. The β-ketoacyl residues consist of several isomers having chain lengths of 14 to 17 carbon atoms.
    Notes: Die Struktur des Peptidantibiotikums Stenothricin wurde durch Chromatographie, Abbau und Derivatbildungsmethoden sowie Massenspektrometrie untersucht. Danach ist Stenothricin mit großer Wahrscheinlichkeit β-Ketoacyl-D-Cys(03H)-L-Val-D-ser-L-Lys-sar-D-αThr-L-Ser-L-Diaminopropionsäure, wobei die β-Ketoacyl-Reste aus mehreren Isomeren mit Kettenlängen zwischen 14 und 17 C-Atomen bestehen.
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  • 4
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Amino Acids and Peptides, I. - The reaction of N-Methylvaline and N-Methylisoleucine with Trifluoroacetic AnhydrideN-Methylvaline, N-methylisoleucine and their alkyl esters react with trifluoroacetic anhydride to form stable, highly volatile 4-alkylidene-3-methyl-2-trifluoro-1,3-oxazolidin-5-ones in high yields. The structures of these compounds were established by proton magnetic resonance, mass spectrometry, und gas chromatography.
    Notes: Die Reaktion von N-Methylvalin, N-Methylisoleucin und deren Alkylester mit Trifluoracetanhydrid führt unter milden Bedingungen in guten Ausbeuten zu 4-Alkyliden-3-methyl-2-trifluormethyl-1,3-oxazolidin-5-onen. Die Struktur dieser leicht flüchtigen, stabilen Verbindungen wurde mittels protonmagnetischer Resonanz, Massenspektrometrie und Gaschromatographie bestimmt.
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  • 5
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Investigations on the Configuration and Conformation of the Nucleoside Residues of the NikkomycinsThe configuration of 5′-amino-5′-deoxy-β-D-allofuranuronosyl derivatives of uracil and 4-formyl-4-imidazolin-2-one could be assigned to the C-terminal nucleoside residues 1 and 2, respectively, of the nikkomycins, according to 1H NMR spectroscopy, circular dichroism, and X-ray analysis. The latter method also showed that 1 and 2 have C-2′-endo-C-1′-exo conformation (21T) with gauche (g+) position of hte CO⊖2-group, trans (t) position of the NH⊕3-group, and anti position of the base. The conformation in solution was determined by 1H NMR spectra and from the 13C-1-H-vicinal couplings and shows only minor deviations from the conformation of the crystal.
    Notes: Den in den Nikkomycinen C-terminal gebundenen Nucleosiden 1 und 2 konnte durch 1H-NMR-Spektroskopie, Circulardichroismus und Kristallstrukturanalyse die Konfiguration von 5′-Amino-5′-desoxy-β-D-allofuranuronosyl-Derivaten des Uracils bzw. 4-Formyl 4 imidazolin-2-ons zugeordnet werden. Die Kristallstrukturanalyse zeigte darüber hinaus, daß 1 und 2 in der C-2′-endo-C-1′-exo-Konformation (21T) vorliegen, wobei die CO⊖2-Gruppe die gauche-Lage (g+), die NH⊕3-Gruppe die trans-Lage (t) und die Base anti-Stellung einnehmen. Die Konformation in Lösung wurde aus 1H-NMR-Spektren und durch Bestimmung der 13C-1H-Vicinalkopplungen ermittelt und weicht nur geringfügig von der Konformation im Kristall ab.
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  • 6
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Sequenz und Konformation von Suzukacillin ADie Sequenz des spannungsabhängige Membranporen bildenden Polypeptidantibiotikums Suzukacillin A wurde bestimmt durch eine Kombination von trifluoracetolytischer Spaltung, präparativer Isolierung von Fragmenten und Analyse durch Gaschromatographie - Massenspektrometrie sowie Felddesorptions- und Fast-Atom-Bombardment-Massenspektrometrie. Suzukacillin A ist ein mikroheterogenes Eikosapeptidantibiotikum (Ac-Aib-L-Ala-Aib-Ala-Aib-Ala(Aib)-Gln-Aib-Aib(Leu)-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib(D-Iva)-Gln-Gln-Phl) mit einer Sequenz, einer α-helicalen Konformation (nach13C-NMR- und Circulardichroismus-Messungen) und membranmodifizierenden Eigenschaften, die dem Alamethicin ähnlich sind.
    Notes: The sequence of the potential-dependent membrane pore-forming polypeptide antibiotic suzukacillin A was determined by a combination of trifluoroacetolytic cleavage, preparative isolation of fragments, and analysis by gas chromatography - mass spectrometry, field-desorption and fast-atom bombardment mass spectrometry. Suzukacillin A is a microheterogeneous eicosapeptide antibiotic (Ac-Aib-L-Ala-Aib-Ala-Aib-Ala(Aib)-Gln-Aib-Aib(Leu)-Aib-Gly-Leu-Aib-Pro-Val-Aib-Aib(D-Iva)-Gln-Gln-Phl) with a sequence, an α-helical conformation (according to 13C NMR and circular dichroism), and membrane-modifying properties related to alamethicin.
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  • 7
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Die C-terminalen Heptapeptide von Suzukacillin A und Alamethicin F30  -  Sequenz, Konformation und SyntheseWährend der Sequenzierung des membranmodifizierenden Eikosapeptidantibiotikums Suzukacillin A wurden zwei C-terminale Heptapeptide durch selektive Trifluoracetolyse erhalten: L-Pro-L-Val-Aib-D-Iva-L-Gln-L-Phl und L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl. Der chromatographische und spektroskopische Vergleich (FAB-MS, FD-MS, 13C-NMR, CD, UV) dieser isolierten natürlichen Fragmente mit dem synthetischen Segment L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl (2) und dem synthetischen C-terminalen Segment von Alamethicin F30 L-Pro-L-Val-Aib-Aib-L-Glu-L-Gln-L-Phl (1) beweist die Sequenz 14-20 von Suzukacillin A.
    Notes: During the sequencing of the membrane-modifying eicosapeptide antibiotic suzukacillin A two C-terminal heptapeptides were obtained via selective trifluoroacetolysis: L-Pro-L-Val-Aib-D-Iva-L-Gln-L-Gln-L-Phl and -Pro-L-Val-Aib-Aib-L-Gln-L-Phl. The chromatographic and spectroscopic comparison (FAB MS, FD MS, 13C NMR, CD, UV) of these isolated natural fragments with the synthetic segment L-Pro-L-Val-Aib-Aib-L-Gln-L-Gln-L-Phl (2) and the synthetic C-terminal segment of alamethicin F30 L-Pro-L-Val-Aib-Aib-L-Glu-L-Gln-L-Phl (1) proved the sequence 14-20 of suzukacillin A.
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  • 8
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Three Novel Amino Acids from the Nikkomycin Complex - Structure Elucidation and SynthesisFrom the culture medium of Streptomyces tendae Tue 901 some new metabolites were characterized: 2-amino-4-hydroxy-3-methyl-4-(2-pyridyl)butanoic acid (1) [nikkomycin E], its isomer 2-amino-4-hydroxy-3-methyl-4-(3-pyridyl)butanoic acid (2) [as N-terminal constituent of the nikkomycins Px (5) and Rz (6)], and 2-amino-4-hydroxy-4-(2-pyridyl)butanoic acid (3) [as N-terminal amino acid of the nikkomycins Kx (7) and Kz (8)]. The structure elucidation was achieved by NMR, mass spectrometry and by comparison with synthetic reference compounds.
    Notes: Aus dem Kulturfiltrat von Streptomyces tendae Tue 901 wurden weitere neue Metabolite charakterisiert: 2-Amino-4-hydroxy-3-methyl-4-(2-pyridyl)buttersäure (1) [Nikkomycin E], die dazu isomere 2-Amino-4-hydroxy-3-methyl-4-(3-pyridyl)buttersäure (2) [als N-terminaler Baustein der Nikkomycine Px (5) und Rz (6)] und 2-Amino-4-hydroxy-4-(2-pyridyl)buttersäure (3) [als N-terminale Aminosäure der Nikkomycine Kx (7) und Kz (8)]. Die Strukturaufklärung erfolgte durch Kernresonanz, Massenspektrometrie und durch Vergleich mit entsprechenden Syntheseprodukten.
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  • 9
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Pure Stereoisomers of the N-terminal Amino Acid of Nikkomycin BPure stereoisomers of 2-amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbutanoic acid (8c), the N-terminal amino acid of nikkomycin B (10a, b), were synthesized by 1,3-dipolar cycloaddition of (ethoxycarbonyl)methanenitrile oxide (2) to the olefines 1, separation of the diastereomeric 4,5-dihydro-3-isoxazolecarboxamides 6, and diastereoselective reductive cleavage and hydrolysis of 6. X-ray structure analysis revealed the absolute configuration (2R,3R,4R) for one pure synthetic stereoisomer of 8c. Gas chromatography on a chiral stationary phase and 1H NMR enabled us to assign the (2S,3S,4S) configuration to the natural amino acid.
    Notes: Reine Stereoisomere von 2-Amino-4-hydroxy-4-(p-hydroxyphenyl)-3-methylbuttersäure (8c), der N-terminalen Aminosäure von Nikkomycin B (10a, b), wurden nach 1,3-dipolarer Cycloaddition von (Ethoxycarbonyl)methannitriloxid (2) an die Olefine 1 und Trennung der diastereomeren 4,5-Dihydro-3-isoxazolcarboxamide 6 durch diastereoselektive reduktive Spaltung und Verseifung von 6 hergestellt. Mit Hilfe eines reinen, synthetischen Stereoisomers von 8c, dessen absolute Konfiguration (2R,3R,4R) durch Kristallstrukturanalyse bestimmt werden konnte, sowie mit Hilfe von Gaschromatographie an chiraler Phase und 1H-NMR gelang es, der natürlichen Aminosäure die Konfiguration (2S,3S,4S) zuzuordnen.
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  • 10
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Strukturaufklärung der Peptidantibiotika Herbicolin A und BDie Struktur der amphiphilen Peptidantibiotika Herbicolin A und B konnte mit physikalischen Methoden sowie durch chemischen Abbau und Partialsynthesen identifiziert werden. Herbicolin B ist ein Lipodepsipeptid der Sequenz DH-Abu-L-Thr-D-aThr-D-Leu-Gly-D-Gln-Gly-N-Me-L-aThr-L-Arg (DH-Abu = 2,3-Dehydro-α-aminobuttersäure), dessen C-terminaler Argininrest mit der Hydroxygruppe von L-Thr lactonisiert und dessen N-Terminus durch (R)-3-Hydroxytetradecansäure acyliert ist. In der Hauptkomponente Herbicolin A ist im Unterschied zu Herbicolin B zusätzlich ein Molekül D-Glucose 1-α-glycosidisch mit der 3-Hydroxytetradecansäure verknüpft. Somit ist Herbicolin A das erste bekannte Glycolipodepsinonapeptid-Antibiotikum.
    Notes: The structures of the amphiphilic peptide antibiotics herbicolin A and B were determined by application of physical methods, chemical degradation, and partial syntheses. Herbicolin B is a lipodepsinonapeptide with the sequence DH-Abu-L-Thr-D-aThr-D-Leu-Gly-D-Gln-Gly-N-Me-L-aThr-L-Arg (DH-Abu = 2,3-dehydro-α-aminobutyric acid). The C-terminal Arg residue forms a lactone ring with the hydroxy group of L-Thr, while the N-terminus is acylated by an (R)-3-hydroxytetradecanoic acid residue. The main component herbicolin A differs from herbicolin B in an additional D-glucose moiety linked in an 1-α-glycosidic bond to the 3-hydroxytetradecanoic acid residue. Thus herbicolin A constitutes the first glycolipodepsinonapeptide antibiotic known so far.
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