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G. REINHARDT, G. BRADLER, K. ECKARDT, D. TRESSELT, W. IHN
1980 Volume 33 Issue 8 Pages
787-790
Published: 1980
Released on J-STAGE: April 12, 2006
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The new antibio tic sarubicin A [red crystals, mp. 194-195°C, C
13H
14N
2O
6 (I)] was isolated from fermentations of a
Streptomyces strain. The compound is moderately active
in vitro against
Micrococcus luteus.
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PRODUCTION, ISOLATION, CHARACTERIZATION AND BIOLOGICAL PROPERTIES
YASUJI KIDD, TAKAHIRO HARADA, TUTOMU YOSHIDA, JUNKO UMEMOTO, YOSHINOBU ...
1980 Volume 33 Issue 8 Pages
791-795
Published: 1980
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A new antibiotic, B-1008 has been isolated from the cultured broth of
Pseudomonas fluorescens No. 101 B-13L. B-1008 is a water-soluble basic substance containing the spermidine moiety and possessing antibacterial activity against a wide range of bacterial species.
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KENICHI YAMAMOTO, TAKEO YOSHIOKA, YASUYUKI KATO, NORIO SHIBAMOTO, KAZU ...
1980 Volume 33 Issue 8 Pages
796-803
Published: 1980
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The structure and stereochemistry of a new β-lactam antibiotic PS-5were determined as shown in Fig. 3.
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CHIKAHIRO URAKAWA, KIN-ICHI NAKANO
1980 Volume 33 Issue 8 Pages
804-809
Published: 1980
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A facile alcoholysis of 7-methoxymitosanes and 5-methoxyindolequinone under basic conditions was discovered and a series of 7-alkoxymitosanes were synthesized from mitomycins A and B using this reaction. They showed strong antibacterial activity against various Grampositive and Gram-negative bacteria and were potent inhibitors of cultivating HeLa S-3 cells
in vitro. Among them, 7-n-propoxy-7-demethoxymitomycin A (2) showed the strongest antitumor activity against solid type Sarcoma-180 in mice.
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JERRY R. MARTIN, PAULETTE JOHNSON, JACK TADANIER, ALMA W. GOLDSTEIN
1980 Volume 33 Issue 8 Pages
810-818
Published: 1980
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The synthesis of 2-deoxyfortimicins A (
15) and B (
11) and 1-deamino-2-deoxy 2-
epi-amino-fortimicins A (
18) and B (
12) is described. Two routes have been developed for synthesis of the key intermediate 2-
O-methanesulfonylfortimicin B (
7). One route involves selective blocking of fortimicin B with
N-benzyloxycarbonyl groups followed by formation of a 4, 5-salicylaldehyde oxazolidine derivative. Subsequent mesylation followed by deblocking gave 7. A more efficient route to 7 involves concomitant salicylaldehyde SCHIFF base and 4, 5-oxazolidine formation followed by mesylation and hydrolysis. The formation of 1, 2(
R)-epiminofortimicin
B (
8) from 7 followed by RANEY nickel reduction gave 2-deoxyfortimicin B and 1-deamino-2-deoxy-2-
epi-aminofortimicin B, which were converted to the corresponding fortimicin A derivatives by selective
N-blocking.
N-acylation and subsequent deblocking. The antibacterial activities of the new fortimicin A derivatives are presented.
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PAUL F. WILEY, DAVID W. ELROD, JAMES M. SLAVICEK, VINCENT P. MARSHALL
1980 Volume 33 Issue 8 Pages
819-823
Published: 1980
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It has been shown that steffimycin (
1) and steffimycin B (
2) are reduced at the C-10 carbonyl by
Actinoplanes utahensis, UCR-5885 and
Chaetomium sp., UCR-4634, respectively. Using cell-free extracts of the latter organism, the optimum conversion time, pH, and enzyme concentration have been determined for the conversion of
2 to
4. The biochemical conversion of
2 has been found to be TPNH linked.
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TAMIO FUJIWARA, YASUO TAKAHASHI, KOICHI MATSUMOTO, EIJI KONDO
1980 Volume 33 Issue 8 Pages
824-829
Published: 1980
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Eight 2-deoxystreptamine-negative (DOS
-) mutants were isolated from various strains of
Bacillus circulans, normally producing butirosin, xylostasin and ribostamycin. These mutants were classified into two groups (converter and secretor) by the simple method of cosynthesis
using agar plate culture. One of the cosynthetic pairs, strain S-11 and strain 236, was selected for further study From the fermentation broth of strain S-11, an intermediate of DOS biosynthesis, S-11-P, was isolated. This compound was converted to butirosin (BTN) effectively by strain 236. The structure of S-11-P was considered to be (1 L or 1 D)-1, 3, 5/2, 4-5-amino-cyclohexanetetrol, and the pathway of DOS biosynthesis is discussed here.
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IKUO IGARASHI, TSUNETOSHI HONMA, TAKASHI FUJIWARA, EIJI KONDO
1980 Volume 33 Issue 8 Pages
830-835
Published: 1980
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The structure of a 2-deoxystreptamine (DOS) precursor named S-11-P, which was isolated by using a DOS negative mutant derived from a xylostasin-producing strain of
Bacillus circulans B15M, has been elucidated as (1 L)-1, 3, 5/2, 4-5-aminocyclohexanetetrol by comparison with an authentic specimen, which was synthesized from kanamycin A.
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TAMIO FUJIWARA, YASUO TAKAHASHI, KOICHI MATSUMOTO, EIJI KONDO
1980 Volume 33 Issue 8 Pages
836-841
Published: 1980
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A new aminoglycoside antibiotic, S-11-A, was isolated from the fermentation broth of the 2-deoxystreptamine negative (DOS
-) mutant of
Bacillus circulans S-11. The structure of S-11-A was elucidated as 1-deamino-1-hydroxyxylostasin, which contains an intermediate of DOS biosynthesis (S-11-P) and has resistance to some aminoglycoside-inactivating enzymes. This is the first finding of antibiotic production by a DOS
- mutant without any supplementation of DOS or a DOS analog, and could be described as a novel method of getting a new aminoglycoside antibiotic.
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BIOSYNTHESIS OF RIFAMYCINS P, Q AND VERDE, NOVEL METABOLITES FROM A MUTANT OF NOCARDIA MEDITERRANEA
R. CRICCHIO, P. ANTONINI, G. SARTORI
1980 Volume 33 Issue 8 Pages
842-846
Published: 1980
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The thiazorifamycins are derived from rifamycin S and cysteine; rifamycins P and Verde are formed by chemical reactions, while rifamycin Q synthesis involves obligatory enzymatic assistance. All antibiotics come from a common six-member precursor lacking C-1 of cysteine; the thiazin-2-one ring of rifamycin Verde retains both C-2 and C-3 of cysteine, while the thiazole ring of rifamycins P and Q retains only C-2, C-3 becoming exocyclic in the ring-contraction C-3 is present in rifamycin Q but not in P.
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III. ISOLATION AND IDENTIFICATION OF FURTHER 8-DEOXYANSAMYCINS OF THE RIFAMYCIN-TYPE
ORESTE GHISALBA, PETER TRAXLER, HERMANN FUHRER, WILHELM J. RICHTER
1980 Volume 33 Issue 8 Pages
847-856
Published: 1980
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A number of minor compounds were isolated from fermentations of the protorifamycin I producing strain
Nocardia mediterranei F 1/24
1, 2) and identified by means of chemical and spectroscopic methods. Two types of structures were identified:
Type 1: modified protorifamycins (derived from protorifamycin I)
Type 2: defective rifamycins (8-deoxyrifamycins).
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ISOLATION AND PROPERTIES OF AN ENZYME SYNTHESIZING ACETYL-L-LEUCINE
KAYOKO SUZUKAKE, HIDEMI HAYASHI, MAKOTO HORI, HAMAO UMEZAWA
1980 Volume 33 Issue 8 Pages
857-862
Published: 1980
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An enzyme which catalyzes acetylation of L-leucine with acetyl-CoA was partially purified from a cell extract of
Streptomyces roseus MA839-Al, a leupeptin producer. The molecular weight of this enzyme is about 27, 000 daltons. The enzyme has fairly broad specificity for acyl donors
(I) and acceptors
(II): as for I, propionyl-CoA was 1/10 as active as acetyl-CoA With L-leucine as the acceptor; as for
II, L-leucyl-D-leucine, L-leucyl-L-leucine, L-arginine, Lleucyl-L-leucyl-L-leucine, L-phenylalanine, L-methionine, L-leucine, glycyl-L-phenylalanine and
L-valine were acetylated in the decreasing order, as opposed to no or slight reactivity of D-phenylalanine, D-leucine, L-histidine, glycine, L-proline and L-glutamic acid. The MICHAELIS constants of acetyl-CoA and L-leucine were about 5×10
-6 M and 6×10
-5 M, respectively. The enzyme is stimulated by Fe
++.
p-Chloromercuribenzoic acid (PCMB), N-ethylmaleimide, Mg
++ and Mn
++ were inhibitory. A leupeptin-nonproducing mutant,
Streptomyces roseus MA839-Al LN-S, derived from the producer strain by acriflavine treatment, also produced this enzvme.
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KENT L. REDMAN, ULFERT HORNEMANN
1980 Volume 33 Issue 8 Pages
863-877
Published: 1980
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Pyruvate, phosphate dikinase (E.C. 2.7.9.1) has been demonstrated in mitomycin-producing
Streptomyces verticillatus. Low levels of activity are detectable in noninduced cultures; however, in alanine or pyruvate containing media the enzyme activity is induced 20 to 40 fold. Assays for the dikinase are subject to very large interferences if pyruvate kinase and adenylate kinase are present together. or if alanine dehydrogenase is present. Chromatography of dialyzed cell-free extracts of induced
S. verticillatus on Cibacron Blue 3G-A Sepharose 6B affords a clean separation of the dikinase from these interfering enzymes which are present in this organism. While the dikinase is eluted in the early fractions, pyruvate kinase and alanine deh drogenase are retained on the column. The dikinase is inhibited by free Cibacron 3G-A Blue and therefore its non-binding to the dye Sepharose column is presently unexplained. Dikinase activity has been detected in two of four strains of
Streptomyces tested and it was found to be absent in rifamycin-producing
Nocardia mediterranei. Lactate dehydrogenase (E.C. 1.1.1.27) activity could not be detected in
S. verticillatus, but alanine dehydrogenase (E.C. 1.4.1.1) has been purified 75 fold in a single step by elution with 0.25 mM NADH from Cibacron Blue 3G-A Sepharose 6B. Further studies have shown the presence of phosphoenolpyruvate carboxylase (E.C. 4.1.1.31) in extracts of
S. verticillatus. This acetyl coenzyme A activated enzyme readily binds to the dye columns and can be specifically eluted with acetyl-coenzyme A. It presumably interacts with the dye on the column by way of its allosteric site.
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M. J. BASKER, R. J. BOON, P. A. HUNTER
1980 Volume 33 Issue 8 Pages
878-884
Published: 1980
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Streptomyces olivaceus ATCC 31365 produces a family of novel β-lactam antibiotics collectively referred to as the olivanic acids. Seven such compounds, MM 4550, MM 13902, MM 17880, MM 22380, MM 22381, MM 22382 and MM 22383 have been identified which have the same carbapenem nucleus but with different side chains attached to the nucleus. The compounds with an (8
S) hydroxyethyl substituent and
cis-orientated β-lactam protons, MM 22380 and MM 22382, and their sulphate esters, MM 17880 and MM 13902, are potent antibiotics with MIC values against Gram-positive and Gram-negative bacteria in the range 0.1-3.1 μg, /ml. The corresponding (8
S) hydroxyethyl compounds with
trans-β-lactam protons, MM 22381 and MM 22383, also have broad-spectrum activity but are rather less potent than the
cis-compound. In addition to their antibiotic activity, the olivanic acids inhibit a number of β-lactamases and enhance the activity of β-lactams such as amoxycillin against β-lactamase-producing bacteria. Significant differences are observed both in antibacterial activities and in β-lactamase inhibition properties when the olivanic acids are compared with the related thienamycin antibiotics which have (8
R) rather than (8
S) stereochemistry and
trans-β-lactam protons.
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HIROFUTO MARUMO, KOZO KITAURA, MAKOTO MORIMOTO, HARUO TANAKA, SATOSHI ...
1980 Volume 33 Issue 8 Pages
885-890
Published: 1980
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The mode of action of nanaomycin A on Gram-positive bacteria such as
Staphylococcus aureus, Bacillus cereus and
Streptococcus faecalis was investigated. Nanaomycin A inhibited the biosyntheses of protein, DNA, RNA and cell-wall peptidoglycan to a similar extent. It increased the exogenous respiration of
S. aureus cells at the minimal inhibitory concentration. The cells preincubated with nanaomycin A showed stimulation of proton influx after addition of N, N'-dicyclo-hexylcarbodiimide, an inhibitor of Ca
++ Mg
++-ATPase. Nanaomycin A seems to interfere with the cytoplasmic membrane or to inhibit coupling of oxidative phosphorylation, followed by secondary inhibitory effect on protein, nucleic acids and cell-wall peptidoglycan biosyntheses.
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DAVID W. HECHT, JOSEPH T. PARISI
1980 Volume 33 Issue 8 Pages
891-894
Published: 1980
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A strain of
Staphylococcus epidermidis was transduced to tobramycin resistance and all transductants were also resistant to kanamycin and neomycin. Results of curing studies also indicated that these resistances were controlled by a single determinant on a plasmid. Agarose gel electrophoresis of the plasmid DNA from parent, cured, and transduced strains showed a single plasmid was responsible and its molecular weight was calculated to be 2.85 ×10
6. Attempts to determine other properties of the organism controlled by this plasmid were unsuccessful.
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FRANÇOIS LE GOFFIC, MARIE-LOUISE CAPMAU, ERÉDÉRIC ...
1980 Volume 33 Issue 8 Pages
895-899
Published: 1980
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(
3H) Tobramycin was used as a probe to determine the relationship between the structure of aminoglycoside antibiotics and their ability to remove this drug from its higher affinity binding site on the ribosome. The dissacharide moieties (neamine, tobramine, gentamine) appeared to have a common binding site, whereas the kanosamine, garosamine and ribose moieties determined the specificity of this binding. Amikacin and butikacin behaved in an anomalous manner in spite of their close structural relationship to tobramycin.
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L. A. DOLAK, T. M. CASTLE, A. DIETZ, A. L. LABORDE
1980 Volume 33 Issue 8 Pages
900-901
Published: 1980
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D. G. MARTIN, C. G. CHIDESTER, D. J. DUCHAMP, S. A. MIZSAK
1980 Volume 33 Issue 8 Pages
902-903
Published: 1980
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JERZY GOLIK, JAN ZIELINSKI, EDWARD BOROWSKI
1980 Volume 33 Issue 8 Pages
904-907
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KLAUS ECKARDT, HORST WETZSTEIN, HEINZ THRUM, WOLFGANG IHN
1980 Volume 33 Issue 8 Pages
908-910
Published: 1980
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SATOSHI OMURA, CHIAKI KITAO, NORIAKI SADAKANE
1980 Volume 33 Issue 8 Pages
911-912
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SATOSHI OMURA, NORIAKI SADAKANE, CHIAKI KITAO, HAJIME MATSUBARA, AKIRA ...
1980 Volume 33 Issue 8 Pages
913-914
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SATOSHI OMURA, HAJIME MATSUBARA, AKIRA NAKAGAWA, AKIO FURUSAKI, TAKESH ...
1980 Volume 33 Issue 8 Pages
915-917
Published: 1980
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