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  • 1
    Electronic Resource
    Electronic Resource
    An unusual pattern of carbohydrate utilization in Corallococcus (Myxococcus) coralloides (Myxobacterales) (1985)
    Springer
    Archives of microbiology 142 (1985), S. 40-44 
    Details
    ISSN: 1432-072X
    Keywords: Myxobacteria ; Carbohydrate metabolism ; Trisaccharide utilization ; Starch utilization ; Pullulanase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The myxobacterium, Corallococcus (Myxococcus) coralloides strain Cc c127, could not utilize mono- and disaccharides, but maltotriose and the polysaccharides starch, amylose, amylopectin, and pullulan stimulated growth. Radioactive CO2 was set free from 14C-labeled starch. When starch was degraded, small amounts of maltose and glucose accumulated in the culture supernatant. Maltotriose, however, appeared only temporarily. Outside the cells, the trisaccharide could not be split into glucose and maltose. Pullulan was hydrolyzed exclusively into a trisaccharide which during growth was immediately consumed. Hexokinase, glucose-6-phosphate dehydrogenase, 6-phosphogluconate dehydrogenase and phosphoglucomutase could readily be demonstrated in cell extracts, but fructose-1,6-diphosphate aldolase was present with low activity only. The data suggest that intracellular glucose is metabolized mainly via the pentose phosphate pathway.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00409234
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  • 2
    Electronic Resource
    Electronic Resource
    Antibiotics from gliding bacteria, LXIV. Isolation and structure elucidation of sorangiolides A and B, novel macrocyclic lactone carboxylic acids from Sorangium cellulosum (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 867-872 
    Details
    ISSN: 0947-3440
    Keywords: Antibiotics ; Sorangium cellulosum ; Macrolides ; Mass spectrometry ; X-ray structure analysis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two novel metabolites, sorangiolide A (1) and B (2), were isolated from the mother liquors and side fractions of the sorangicin A pilot-scale production. Their structures were elucidated by 2D-NMR spectroscopy and mass spectrometry as 18-membered macrolactones with a C11-carboxylic acid side chain. Sorangiolide B (2) differs from A (1) by an additional hydroxyl group at C-6 in the side chain. The absolute configuration of sorangiolide A (1) was established by X-ray structure analysis. The sorangiolides show a weak antibiotic activity against Gram-positive bacteria.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199505125
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  • 3
    Electronic Resource
    Electronic Resource
    Antibiotics from Gliding Bacteria, LXXVIIIPart LXXVII: Ref.. Ripostatin A, B, and C: Isolation and Structure and Structure Elucidation of Novel Metabolites from Sorangium cellulosum (1996)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1996 (1996), S. 1657-1663 
    Details
    ISSN: 0947-3440
    Keywords: Antibiotics ; Polyketides ; Sorangium cellulosum ; RNA polymerase inhibitors ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three closely related new metabolites named ripostatins were isolated from the myxobacterium Sorangium cellulosum and their structures elucidated by spectroscopic methods. Two of them, ripostatin A (1a, b) and B (2a), are 14-membered macrolides with an acetic acid and a phenylalkyl side chain, whereas the third metabolite ripostatin C (3a) is an acyclic derivative of ripostatin A. By application of the method of Helmchen the absolute stereochemistry could be determined as (11R,13R) for ripostatin A, 11R,13S,15R for ripostatin B and 11S for ripostatin C. The polyketide origin of A was revealed by feeding experiments with 13C-labeled precursors demonstrating the incorporation of one molecule of phenylacetic acid derived from phenylalanine, one propionate unit, and ten acetate units.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199619961026
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  • 4
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, XVII. Myxopyronin A und B - zwei neue Antibiotika aus Myxococcus fulvus Stamm Mx f50 (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1656-1667 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from gliding Bacteria, XVII. - Myxopyronin A and B - Two Novel Antibiotics from Myxococcus fulvus Strain Mx f50From the gliding bacterium Myxococcus fulvus strain Mx f50 two antibiotics, named myxopyronin A and B, have been isolated and shown to possess the structures 9a and 9b. The two new compounds are 3-acyl-4-hydroxy-α-pyrones with an N-alkenylcarbamate function uncommon to natural products.
    Notes: Aus dem Kulturüberstand des Gleitenden Bakteriums Myxococcus fulvus Stamm Mx f50 (Myxobacterales) wurden zwei Myxopyronin A und B genannte Antibiotika isoliert und konstitutionell aufgeklärt. Es handelt sich um die Verbindungen 9a, b mit einer 3-Acyl-4-hydroxy-α-pyron-Struktur und einer für Naturstoffe ungewöhnlichen N-Alkenyl-Carbamat-Funktion.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319831003
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  • 5
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, XXIV. Corallopyronin A, B und C - drei neue Antibiotika aus Corallococcus coralloides Cc c127 (Myxobacterales) (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 822-836 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Gliding Bacteria, XXIV. - Corallopyronin A, B, and C - Three Novel Antibiotics from Corallococcus coralloides, Cc c127 (Myxobacterales)Three new antibiotics, corallopyronin A (1), B (2), and C (4) have been isolated from the culture broth of Corallococcus coralloides, strain Cc c127 (DSM 2550), by phase distribution and chromatography. The corallopyronins are closely related to myxopyronin A (5) and B (6), two homologous 3-acyl-4-hydroxy-α-pyrons with an α,β-unsaturated methyl carbamate function. Structurally the new antibiotics differ from the myxopyronins in an elongated 3-acyl side chain with two additional double bonds and one hydroxy function in corallopyronin A (1) and B (2) or an 3-acyl residue with a tetrahydrofuran ring in the component C (4).
    Notes: Aus dem Kulturmedium von Corallococcus coralloides, Stamm Cc c127 (DSM 2550), wurden drei neue Antibiotika, die Corallopyronine A (1), B (2) und C (4) durch Phasenverteilung und Chromatographie isoliert. Die Corallopyronine sind mit den Myxopyroninen A (5) und B (6), zwei homologen 3-Acyl-4-hydroxy-α-pyronen mit α,β-ungesättigter Methylcarbamatfunktion, nahe verwandt. Die neuen Antibiotika unterscheiden sich strukturell von den Myxopyroninen durch einen verlängerten 3-Acylrest mit zwei zusätzlichen Doppelbindungen und einer Hydroxyfunktion in Corallopyronin A (1) und B (2) oder durch einen 3-Acylrest mit einem Tetrahydrofuranring in der Komponente C (4).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850418
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  • 6
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, XXXV. Isolierung und Strukturaufklärung der Saframycine Mx 1 und Mx 2, neue antitumor-aktive Antibiotika aus Myxococcus xanthus (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 475-481 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Gliding Bacteria, XXXV1). - Isolation and Structure Elucidation of Saframycin Mx 1 and Mx 2, New Antitumor-Active Antibiotics from Myxococcus xanthusThe workup procedure, the isolation, and structure elucidation of new antitumor-active saframycins Mx 1 (1) and Mx 2 (2) are described. Their relative and absolute configurations are derived from NMR studies and by comparing the optical rotations with those of known safracins. Acidic hydrolysis of 1 and 2 yields L-alanine.
    Notes: Es werden die Aufarbeitung, die Isolierung und Strukturaufklärung neuer antitumor-aktiver Saframycine Mx 1 (1) und Mx 2 (2) vorgestellt, deren relative und absolute Konfiguration aus NMR-Untersuchungen und Vergleich der optischen Drehwerte mit denen bekannter Safracine ermittelt werden. Aus sauren Hydrolysaten von 1 und 2 wird L-Alanin erhalten.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880518
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  • 7
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, XXXVIII. Natürliche Strukturvarianten von Sorangicin A aus Sorangium cellulosum, So ce12 (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 213-222 
    Details
    ISSN: 0170-2041
    Keywords: Macrolide-polyether antibiotics ; Sorangicin B ; Sorangicin A variants ; Sorangium cellulosum ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Gliding Bacteria, XXXVIII1). - Naturally Occurring Structural Variants of Sorangicin A Produced by Sorangium cellulosum, So ce12In addition to Sorangicin A (1) from fermentation extracts of Sorangium cellulosum a deoxygenated modification sorangicin B (2), the sorangicins A1 (3), A2 (4), and A3 (5) with isomeric triene moieties, and as isomers, in which the tetrahydrofuran ring has been opened, the sorangicins C (9), C2 (6), C3 (8), C4 (7) were isolated and their structures elucidated. The 21-O-β-D-glucosides sorangioside A (11) and B (12) and the 21-O-β-D-6′-deoxyglucosides sorangioside C (13) and C4 (14) were also found.
    Notes: Neben Sorangicin A (1) wurden aus den Fermentationsextrakten von Sorangium cellulosum eine desoxygenierte Variante Sorangicin B (2), die Sorangicine A1 (3), A2 (4) und A3 (5) mit isomerisiertem Trienteil und als Isomere, bei denen der Tetrahydrofuranring geöffnet ist, die Sorangicine C (9), C2 (6), C3 (8) und C4 (7) isoliert und in ihrer Struktur aufgeklärt. Zusätzlich wurden die 21-O-β-D-Glucoside Sorangiosid A (11) und B (12) und die 21-O-β-D-6′-Desoxyglucoside Sorangiosid C (13) und C4 (14) gefunden.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890142
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  • 8
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, XXXIX. Biosynthese von Sorangicin A in Sorangium cellulosum, So ce12 (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 309-313 
    Details
    ISSN: 0170-2041
    Keywords: Sorangicin ; Biosynthesis ; [13C]Acetates ; [13C]Methionine ; [13C]Carbonate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Antibiotics from Gliding Bacteria, XXXIX1). - Biosynthesis of Sorangicin A in Sorangium cellulosum, So ce12The biogenesis of sorangicin A (1) was studied by feeding experiments with single and doubly labeled [13C]acetates as well as sodium [13C]hydrogencarbonate and [methyl-13C]methionine. Accordingly, 1 is assembled by linear condensation of twenty acetate units onto a malonate starter unit, which is completely preserved in 1. The carboxy group of the malonyl-CoA ester, identical with C-1 in 1, is labeled by [13C]carbonate or by carbon originating from [1-13C]acetate. The four methyl groups in 1 are derived from methionine.
    Notes: Die Biogenese von Sorangicin A (1) wurde durch Verfüttern von einfach und doppelt 13C-markierten Acetaten sowie von [13C]Natriumhydrogencarbonat und [Methyl-13C]Methionin untersucht. Demnach wird 1 durch lineare Kondensation von zwanzig Acetateinheiten an einen Malonatstarter aufgebaut, der vollständig in 1 enthalten ist. Die Carboxylgruppe des Malonyl-Co-A-esters, identisch mit C-1 in 1, wird durch [13C]Carbonat oder durch Kohlenstoff aus [1-13C]Acetat markiert. Die vier Methylgruppen in 1 stammen aus Methionin.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890155
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  • 9
    Electronic Resource
    Electronic Resource
    Antibiotics from gliding bacteria, XLII. Chemical modification of sorangicin A and structure  -  Activity relationship I: Carboxyl and hydroxyl group derivatives (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 975-988 
    Details
    ISSN: 0170-2041
    Keywords: Antibiotics ; Sorangicin A derivatives ; Structure - activity relationship ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of selectively protected sorangicin A derivatives and their application in the modification of the hydroxyl groups and the carboxyl group in sorangicin A (1) is described. Esters, amides, and sorangicins modified at the hydroxyl groups were prepared and their activities against Staphylococcus aureus, Escherichia coli, and their in vitro inhibition of RNA polymerase were examined. Although no sorangicin A derivatives with superior biological activity were observed, some derivatives completely retained their antibiotic activity or were slightly improved in their activity with certain strains.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001178
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  • 10
    Electronic Resource
    Electronic Resource
    Antibiotika aus Gleitenden Bakterien, L - Chemische Modifikation von Sorangicin A und Struktur-Wirkungs-Beziehung II: Derivate aus Reduktions-, Oxidations- und Umlagerungsreaktionen (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 293-304 
    Details
    ISSN: 0170-2041
    Keywords: Antibiotics ; Sorangicins ; Macrolide-polyether antibiotics ; Structure-activity relationship ; Enzymes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Antibiotics from Gliding Bacteria, L. - Chemical Modification of Sorangicin A and Structure-Activity Relationship II: Derivatives Obtained by Reduction, Oxidation and Rearrangement ReactionsThe synthesis of 38 derivatives of sorangicin A (1) with modifications of the three hydroxyl groups and the conjugated triene is described. By oxidation and reduction reactions 21-desoxy-21-oxo sorangicin (8), 21-epi-sorangicin (9) and 21-desoxysorangicins 14, 15 were obtained. With protection of the 21,22-diol the 24,25-didehydro-25-desoxysorangicin (18), 25-desoxy-25-oxosorangicins 21, 22 and 25-epi-sorangicins 23, 24 were prepared. Further, the 25-oxo derivatives 21, 22 were transformed into the oximes 25-28 and the 25-desoxy-25,25-difluoro sorangicin (31). Catalytic reduction of sorangicin A (1) gave the 37,43-dihydro derivative 35, thermolysis the cyclohexadienes 36, 37 and fluoride-induced isomerisation the 36,38,40-trienol ethers 38, 39. - Activities against Staphylococcus aureus, Escherichia coli, and in vitro inhibition of RNA polymerase of selected derivatives were examined. With most compounds a reduced biological activity was observed, some derivatives retained their activity (23-28, 31) and three were improved for certain strains (18, 21, 22) although they showed reduced enzyme inhibition activity.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930150
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