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  • 11
    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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  • 12
    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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  • 13
    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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  • 14
    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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  • 15
    Electronic Resource
    Electronic Resource
    Reaktionen von Aminosäuren und Peptiden, IV. Synthese von Furanderivaten aus N-Methylaminosäuren (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1606-1609 
    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, IV. - Synthesis of Furan Derivatives from N-Methyl Amino AcidsIn the reaction of N-methyl homophenylalanine and N-methyl norleucine with hexafluoroacetic anhydride the expected 1,3-oxazolidin-5-one derivatives are formed only as by-products. As main products 3-[methyl(trifluoroacetyl)amino]-2,5-bis(trifluoromethyl)furan derivatives could be isolated, the structures of which were identified by spectroscopic methods.
    Notes: Bei der Reaktion von N-Methylhomophenylalanin und N-Methylnorleucin mit Hexafluoracetanhydrid entstehen die erwarteten 1,3-Oxazolidin-5-on-Derivate nur als Nebenprodukte. Als Hauptprodukte konnten 3-[Methyl(trifluoracetyl)amino]-2,5-bis(trifluormethyl)furan-Derivate isoliert werden, deren Konstitutionen mit spektroskopischen Methoden ermittelt wurden.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810910
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  • 16
    Electronic Resource
    Electronic Resource
    Die Struktur von Stenothricin - Korrektur eines früheren Strukturvorschlags (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1672-1684 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Structure of Stenothricin - Revision of a Previous Structure AssignmentA deviation from the previously assumed molecular mass was proved by fast-atom bombardment mass-spectrometry for the peptide antibiotic stenothricin. Recent investigations of a partial hydrolyzate revealed the presence of α-ketobutyrylvaline formed by hydrolysis of an α,β-dehydroaminobutyric acid (DH-Abu) moiety. Fragments obtained by partial hydrolysis of stenothricin after catalytic hydrogenation show that the previously identified tripeptide D-aThr-L-Ser-L-Dpr is linked over DH-Abu to the tetrapeptide L-Val-D-Ser-L-Lys-Sar. The carboxy group of Sar is esterified with the hydroxy group of D-aThr. The N-terminus is formed by D-cysteic acid, which is N-acylated by β-ketoacyl residues and is connected to the cyclic octapeptide lactone via the amino group of D-a Thr.
    Notes: Die durch Fast-Atom-Bombardment-Massenspektrometrie gegenüber früheren Annahmen nachgewiesene Abweichung der Molmasse von Stenothricin erforderte eine erneute Untersuchung dieses Peptidantibiotikums. Gegenüber früheren Befunden konnte im Partialhydrolysat zusätzlich α-Ketobutyrylvalin identifiziert werden, das durch Verseifung von α,β-Dehydroaminobuttersäure (DH-Abu) entsteht. Nach katalytischer Hydrierung von Stenothricin durch Partialhydrolyse erhaltene Fragmente zeigen, daß das schon früher identifizierte Tripeptid D-aThr-L-Ser-L-Dprüber DH-Abu an das Tetrapeptid L-Val-D-Ser-L-Lys-Sar gebunden ist. Die Carboxygruppe von Sar ist außerdem mit der Hydroxygruppe von D-aThr verestert. Die durch β-Ketoacylreste N-acylierte D-Cysteinsäure bildet den N-Terminus und ist über die Aminogruppe von D-aThr mit dem Octapeptidlacton verknüpft.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419841007
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  • 17
    Electronic Resource
    Electronic Resource
    The C-Terminal Heptapeptides of Suzukacillin A and Alamethicin F30  -  Sequence, Conformation, and Synthesis (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 365-377 
    Details
    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.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850212
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  • 18
    Electronic Resource
    Electronic Resource
    Drei neue Aminosäuren aus dem Nikkomycin-Komplex  -  Strukturaufklärung und Synthese (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 407-421 
    Details
    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.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619860301
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  • 19
    Electronic Resource
    Electronic Resource
    Partialsynthese der Nikkomycine Bx und Kx sowie unnatürlicher Stereoisomerer und Strukturanaloga (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 803-807 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Partial Synthesis of Nikkomycins Bx, Kx and Unnatural Stereoisomers and Structural AnaloguesNikkomycin Bx (8a) was prepared by connecting synthetic (2S,3S,4S)-2-amino-4-hydroxy-4-(4-hydroxyphenyl)-3-methyl-butanoic acid (1a) to natural 1-(5′-amino-5-deoxy-β-D-allofuranuronosyl)-4-formyl-1H-imidazol-2(3H)-one (6a). In an analogous way the (2S,3R,4R)-stereoisomer 8b, the p-methoxy derivative 8c, nikkomycin Kx (8d), and its analogues 8e and 8f, as well as the nikkomycin Z analogues 8g and 8h were prepared. Of the synthetic products only the stereoisomers 8a and 8d, corresponding to the natural products, showed the expected fungicidal activity. The p-methoxyphenyl derivative 8c is only active against yeasts, while the nikkomycin analogues 8e-8h are inactive against fungi.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870832
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  • 20
    Electronic Resource
    Electronic Resource
    What is the Structure of Peptide Antibiotic Tü 1718 B? Previously Proposed Structure Disproved by Synthesis (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1281-1287 
    Details
    ISSN: 0170-2041
    Keywords: N-Valyl-dihydroxyhomoproline ; Streptomyces antibioticus ssp. Tü 1718 B ; Antibiotics ; Peptides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two stereoisomers (1a and 1b) of N-(L-valyl)-2′,5-dihydroxyhomoproline, the proposed structure of the dipeptide antibiotic Tü 1718 B, were synthesized by starting from natural (2S,4R)-hydroxyproline. The 1H- and 13C-NMR spectra of 1a and 1b clearly differ from the corresponding spectra of the natural product. From both synthetic stereoisomers characteristic mass spectra were obtained after esterification and trifluoroacetylation. Isomer 1a is present as a mixture of two stable conformers, as indicated by peak splitting in the1H-NMR spectra, which disappears at higher temperature, while 1b exits as a single conformer. Both synthetic stereoisomers are antibiotically inactive.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201212
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