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  • 21
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen, 195. Konstitution von Ophiocordin, einem Antibiotikum mit antifungischen Eigenschaften (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2221-2226 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolites of Microorganisms, 195. The Structure of Ophiocordin, an Antibiotic with Antifungal ActivityThe structure of the antibiotic Ophiocordin (9), which exhibits antifungal activity, was elucidated by chemical degradation, mass spectrometry, and NMR. Ophiocordin contains a novel 3-amino-hexahydro-4-hydroxyazepin system (5), which is esterified with 4-hydroxybenzoic acid and connected to 3,3′,5′-trihydroxy-2,4′-carbonylbis[benzoic acid] (7) via an amide bond between the 1-carboxy group and the amino group of the azepin system.
    Notes: Die Konstitution des antifungisch wirksamen Antibiotikums Ophiocordin (9) konnte durch chemischen Abbau, Massenspektrometrie und Kernresonanz aufgeklärt werden. Ophiocordin enthält ein neuartiges 3-Aminohexahydro-4-hydroxyazepin-System (5), an das 4-Hydroxybenzoesäure esterartig und 3,3′,5′-Trihydroxy-2,4′-carbonylbis[benzoesäure] (7) über die Carboxylgruppe in 1-Stellung säureamidartig gebunden ist.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130617
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  • 22
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen. 253. Mitteilung252, Mitteilung. Hormaomycin, ein neues Peptid-lacton mit morphogener Aktivität auf Streptomyceten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 426-437 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hormaomycin, a Novel Peptide Lactone with Morphogenetic Activity on StreptomycesA culture identified as Streptomyces griseoflavus (strain W-384) has been found to produce a novel peptide-lactone antibiotic designated hormaomycin (6). The empirical molecular formula of the compound is established to be C55H69ClN10O14. The constituent amino acids of the antibiotic are suggested to be allothreonine (1; 1), isoleucine (2; 1), 3-methyl-phenylalanine (3; 2), and, for the first time identified from a natural source, 4-[(Z)-prop-1-enyl]-proline (4; 1) and 3-(2-nitrocyclopropyl)-alanine (5; 2). The amino acids were delivered by acidic hydrolysis and assigned by high-resolution- GC/MS analysis (after transformation to derivatives) in combination with extended 2D-NMR experiments of the antibiotic itself. From the latter, it became plausible that the N-terminus of the peptide chain is acylated by a Cl-containing derivative of 1H-pyrrol-2-carboxylic acid. Hormaomycin is active against some Gram-positive bacteria. In addition, the antibiotic exhibits potent aerial mycelium-inducing activity and effects the production of antibiotics.
    Notes: No abstract.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720303
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  • 23
    Electronic Resource
    Electronic Resource
    Unusual and Novel C11H16 Hydrocarbons from the Southern Australian Brown Alga Dictyopteris acrostichoides (Phaeophyceae) (1992)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 75 (1992), S. 734-744 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Unusual and novel C11H16 olefins with (E)- or (E,E)-configuration instead of the previously known (Z)- or (E,Z)-configuration at the double bond(s) within the longer side chain are the main products of the Australian phaeophyte Dictyopteris acrostichoides. This configuration anomaly refers to all four series of alicyclic C11H16 hydrocarbons, namely the disubstituted cyclopentenes and cyclopropanes, as well as the monosubstituted cycloheptadienes and cyclopentenes. Chiral compounds within the above series have the same absolute configuration. The two (cyclopent-3-enyl)hexa-1, 3-dienes 11 and 13 are found for the first time. The absolute configuration and optical purity of the hydrocarbons are determined by gas chromatography on modified cyclodextrins as chiral stationary phases. The synthesis of chiral references via lipase-catalyzed resolutions is described.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19920750309
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  • 24
    Electronic Resource
    Electronic Resource
    Synthesis and Absolute Configuration of the C12-Terpenoid Dehydrogeosmin from the Flower Scents of Rebutia marsoneri and Dolichothele sphaerica (Cactaceae); a new approach to bis-angularly substituted trans-decalins (1993)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 76 (1993), S. 1949-1955 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Optically pure(+)-(4S, 4aS, 8aS)-1,2,3,4,4a,5,8,8a-octahydro-4,8a-dimethylnaphthalen-4a-ol((+)-1; dehydrogeosmin) is released from flower heads of the two cactaceae Rebutia marsoneri and Dolichothele spharica. The absolute configuration of (+)-1 is identical with that of the known microbial metabolial geosmin (-)-2. The key reactions of the synthesis of 1 are the kinetically controlled transesterification of the primary alcohol 4 using a lipase from Candida cyclindracea and the stereo-and regiospecific angular alkylation of a cis-decalin skeleton by a Lewis-acid-assisted ring opening of the quaternary epoxy-alcohol 3 with MeMgBr/Cul. The sequence provides a new entry into the class of bis-angularly substituted trans-decalins.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19930760513
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  • 25
    Electronic Resource
    Electronic Resource
    Reaktionen von Aminosäuren und Peptiden, II. Darstellung von 2-Aminooxazolderivaten aus Peptidamiden mit Hexafluoracetanhydrid (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 973-985 
    Details
    ISSN: 0170-2041
    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, II. - Preparation of 2-Aminooxazole Derivatives from Peptide Amides with Hexafluoroacetic AnhydrideC-Terminal amino acid amide residues of peptide amides react with hexafluoroacetic anhydride to form stable 5-(trifluoroacetylamino)oxazole derivatives. Several representatives of this class of compounds have been synthesized and their structures determined by 1H-NMR and mass spectrometry and by their chemical reactions. The heterocyclization reaction can be used for the formation of volatile derivatives in the analysis of peptide amides on a microgram scale and for the identification of the C-terminal amino acid residue in peptide amides.
    Notes: C-Terminale Aminosäureamidreste von Peptidamiden reagieren mit Hexafluoracetanhydrid in guten Ausbeuten zu stabilen 5-(Trifluoracetylamino)oxazolderivaten. Verschiedene Vertreter dieser Verbindungen wurden dargestellt und ihre Struktur durch 1H-NMR-, Massenspektrometrie und chemische Reaktionen charakterisiert. Die Heterocyclisierungsreaktion kann im Mikrogramm-Maßstab zur Herstellung flüchtiger Derivate bei der Analytik von Peptidamiden und zur Identifizierung der C-terminalen Aminosäure von Peptidamiden benutzt werden.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919790708
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  • 26
    Electronic Resource
    Electronic Resource
    Synthese der N-terminalen Aminosäure der Nikkomycine I, J, X und Z (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 1615-1622 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of the N-Terminal Amino Acid of the Nikkomycins I, J, X, and ZA mixture of four stereoisomers of 2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbutanoic acid (14), the N-terminal amino acid of the nikkomycin antibiotics could be synthesized in a twelve-step procedure. By comparison of 1H NMR spectra, mass spectra and of the gas chromato-graphic behaviour of various derivatives the constitution and relative configuration of the natural compound has been confirmed.
    Notes: Ein Gemisch aus vier Stereoisomeren von 2-Amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbuttersäure (14) der N-terminalen Aminosäure der Nikkomycin-Antibiotika konnte in einer zwölfstufigen Synthese dargestellt werden. Durch Vergleich der 1H-NMR-Spektren, Massenspektren und des gaschromatographischen Verhaltens verschiedener Derivate von Synthese- und Naturprodukt wird die Richtigkeit der angenommenen Konstitution und relativen Konfiguration bestätigt.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820904
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  • 27
    Electronic Resource
    Electronic Resource
    Sequence and Conformation of Suzukacillin A (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1041-1062 
    Details
    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.
    Additional Material: 13 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850518
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  • 28
    Electronic Resource
    Electronic Resource
    Synthese reiner Stereoisomerer der N-terminalen Aminosäure von Nikkomycin B (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 2165-2177 
    Details
    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.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519851107
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  • 29
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen, 182. Aufklärung der Struktur des Nucleosidantibiotikums Nikkomycin X (1979)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1979 (1979), S. 1494-1502 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Metabolites of Microorganisms, 182.  -  Structure Elucidation of the Nucleoside Antibiotic Nikkomycin XIn addition to the previously described nikkomycin Z, the structure of which could be confirmed, a new chitin synthase inhibiting component, nikkomycin X, could be isolated from the culture filtrate of Streptomyces tendae. Nikkomycin X is a structural isomer of nikkomycin Z and contains a 4-formyl-4-imidazolin-2-one unit instead of uracil. The structure was established by spectroscopic methods, chemical degradation and partial synthesis. Biological activity and antibiotic spectra of the two nikkomycins are similar.
    Notes: Neben dem bereits früher beschriebenen Nikkomycin Z, dessen Struktur bestätigt werden konnte, wurde aus dem Kulturfiltrat von Streptomyces tendae eine weitere die Chitinsynthase hemmende Komponente, Nikkomycin X, isoliert, die mit Nikkomycin Z strukturisomer ist, aber anstelle von Uracil 4-Formyl-4-imidazolin-2-on enthält. Die Struktur wurde mit spektroskopischen Methoden, durch chemischen Abbau und durch Teilsynthesen bewiesen. Die biologischen Aktivitäten und die Wirkungsspektren der beiden Nikkomycine sind ähnlich.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197919791007
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  • 30
    Electronic Resource
    Electronic Resource
    Konfiguration von 2-Amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbuttersäure, der N-terminalen Aminosäure der Nikkomycine (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1728-1735 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Configuration of 2-Amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbutyric Acid, the N-Terminal Amino Acid of the NikkomycinsThe N-ethylthio(thiocarbonyl)derivative 2 of the N-terminal amino acid 1 of the nikkomycin antibiotics shows a positive Cotton effect in its circular dichroism spectrum and therefore 1 is assigned to the L-series. The relative configuration of the C atoms 3 and 4 was ascertained by 1H-NMR investigations and crystal structure analysis. Accordingly, 1 is assigned the configuration 2S,3S,4S.
    Notes: Das N-Ethylthio(thiocarbonyl)derivat 2 der N-terminalen Aminosäure 1 der Nikkomycin-Antibiotika weist Circulardichroismus mit positivem Cottoneffekt auf und 1 ist daher der L-Reihe zu-zuordnen. Die relative Konfiguration an den C-Atomen 3 und 4 wurde durch 1H-NMR- und Kristallstrukturuntersuchungen bestimmt. Danach hat 1 die Konfiguration 2S,3S,4S.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019801112
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