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I. BIOSYNTHETIC STUDIES WITH THE BLOCKED MUTANTS OF MICROMONOSPORA SAGAMIENSIS
HIROSHI KASE, YOSHIHIRO ODAKURA, KIYOSHI NAKAYAMA
1982 Volume 35 Issue 1 Pages
1-9
Published: 1982
Released on J-STAGE: April 12, 2006
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The mutants blocked in the gentamicin C
1 production were derived from a sagamicin producing strain of
Micromonospora sagamiensis. The intermediates produced by these mutants were isolated and properly identified. Comparing the biotransformation activities in the resting cells of the mutants with those of a DOS idiotroph, KY 11525, the blocked steps in sagamicin and gentamicin biosynthesis were proposed in each mutant. Mutant KY 11564 was found to produce gentamicin C
2a (C-6'-epimer of gentamicin C
2) together with gentamicin C
1a, and sagamicin. KY 11525 transformed gentamicin C
2a into C
2 and C
1, whereas KY 11564 lacked the activity. KY 11565 produced gentamicin X
2 and antibiotic G-418, and lacked 6'-amino substitution activities. KY 11566 appeared to be partially blocked in 6'-
N-methylation activities, and the major products were gentamicin C
2a and C
1a. From these results, sagamicin biosynthesis in
M. sagamiensis is discussed.
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I. TAXONOMIC STUDIES ON THE PRODUCING MICROORGANISMS
YOSHIMI KAWAMURA, YUKIO YASUDA, MIKAO MAYAMA, KENTARO TANAKA
1982 Volume 35 Issue 1 Pages
10-14
Published: 1982
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Two streptomycete isolates, PA-31088 and PA-39504, were found to produce new carbapenem antibiotics, asparenomycins A, B and C. Strain PA-31088 was identified as a new species of
Streptomyces and the name
Streptomyces tokunonensis sp. nov. proposed. Strain PA-39504 was identified as
Streptomyces argenteolus.
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II. ISOLATION AND CHEMICAL CHARACTERIZATION
JUN'ICHI SHOJI, HIROSHI HINOO, RYUZI SAKAZAKI, NAOKI TSUJI, KAZUO NAGA ...
1982 Volume 35 Issue 1 Pages
15-23
Published: 1982
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New carbapenem antibiotics named asparenomycins A, B and C were isolated from the fermentation broths of
Streptomyces tokunonensis sp. nov. and of
Streptomyces argenteolus. The fermentative production, isolation and physico-chemical properties of these antibiotics are described.
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III. STRUCTURES
NAOKI TSUJI, KAZUO NAGASHIMA, MASAAKI KOBAYASHI, JUN'ICHI SHOJI, TOSHI ...
1982 Volume 35 Issue 1 Pages
24-31
Published: 1982
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The structures of asparenomycins were elucidated as new carbapenem antibiotics having a hydroxyisopropylidene group on the β-lactam ring. The stereochemistry was unequivocally confirmed by X-ray analysis and chemical degradation.
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IV. ANTIBACTERIAL ACTIVITY
YASUO KIMURA, KIYOSHI MOTOKAWA, HIROSHI NAGATA, YASUO KAMEDA, SHINZO M ...
1982 Volume 35 Issue 1 Pages
32-38
Published: 1982
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Asparenomycins (ASM) A, B and C, new members of the carbapenem family of antibiotics, are broad spectrum antibiotics with activity against Gram-positive and Gram-negative bacteria. ASM A was bactericidal to both aerobic and, anaerobic bacteria although morphological alterations of ASM A exposed cells differed significantly between
Escherichia coli and
Bacteroides firagilis; with the former ovoidal forms were produced while with the latter elongated forms were seen. Synergistic activities were observed with a combination of ASM A and ampicillin (ABPC) against various ABPC-resistant bacteria presumably as a result of the inhibition by ASM A of β-lactamases. ASM A showed relatively weak therapeutic activity against
E. coli infected mice, because of instability in body fluids, a common property of the carbapenem family of antibiotics.
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KAZUHISA MURAKAMI, MASAYOSHI DOI, TADASHI YOSHIDA
1982 Volume 35 Issue 1 Pages
39-45
Published: 1982
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Asparenomycins (ASMs) A, B and C inhibited a wide range of β-lactamases including both cephalosporinases and penicillinases usually at concentrations less than 3 μM. On studying the mechanism of inhibition of β-lactamases produced by Gram-negative bacteria by ASM A it was concluded that ASM A inhibited the β-lactamases by acylating the enzymes. This conclusion was reached from the following observations. i) The inhibition was progressive with time. ii) The inhibitor formed stable complexes with the enzyme. iii) Before completing inhibition of one molecule of the enzyme, 1.8 molecules of the inhibitor were hydrolyzed.
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JERRY R. MARTIN, PAULETTE JOHNSON, JACK TADANIER, MOMIR CIROVIC, RUTH ...
1982 Volume 35 Issue 1 Pages
46-57
Published: 1982
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The preparation of 1, 2-anhydro-2', 6'-di-
N-benzyloxycarbonyl-1 -deaminofortimicin B-4, 5-carbamate (4) and its conversion to the two diastereomeric 2', 6'-di-N-benzyloxycarbonyl-1-deamino-2-deoxy-1, 2-epoxyfortimicin B-4, 5-carbamates
7 and
13 are described. The olefin
4 was used for preparation of 1-deamino-2-deoxyfortimicin A (
6d) while the β-epoxide
13 was used for the preparation of 1, 2-di-epi-fortimicin A (
17b) and 2-amino-1-deamino-2-deoxy-1-hydroxyfortimicin A (
19c). The in vitro antibacterial activities of
6d,
17b and
19c are reported.
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TAKAHIRO TORH, TSUTOMU TSUCHIYA, SUMIO UMEZAWA
1982 Volume 35 Issue 1 Pages
58-61
Published: 1982
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Synthesis and antibacterial activities of the title compounds are described.
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M. P. WILLIAMSON, D. GAUVREAU, D. H. WILLIAMS, M. J. WARING
1982 Volume 35 Issue 1 Pages
62-66
Published: 1982
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Nuclear magnetic resonance has been employed to characterize fourteen new antibiotics belonging to the quinoxaline group, produced by feeding aromatic acids to
Streptomyces echinatus. Twelve of the antibiotics are the expected substituted quinomycins and adopt conformations very similar to that of echinomycin. This is discussed in relation to their different DNA-binding characteristics. The other two antibiotics are triostins, supporting the proposal that triostins serve as biosynthetic precursors of the quinomycins.
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HIDEKI KAMBARA, SHINZABURO HISHIDA, HIROSHI NAGANAWA
1982 Volume 35 Issue 1 Pages
67-73
Published: 1982
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Nonvolatile and thermolabile antibiotics are investigated both by field desorption and by secondary ion mass spectrometry (SIMS). It has been successfully demonstrated that these two methods are complementary in obtaining informations about molecular weight and structure. Although FD is most widely used for the investigation of nonvolatile biologically active compounds, there are some compounds of which FD can not provide reliable information. SIMS is successfully applied to obtain structural information of these compounds. SIMS spectra frequently depend on the surface conditions of sample holder materials.
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ORESTE GHISALBA, RUTH ROOS, THOMAS SCHUPP, JAKOB NÜESCH
1982 Volume 35 Issue 1 Pages
74-80
Published: 1982
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The transformation of rifamycin S into rifamycins B and L was reinvestigated in order to establish more detailed pathways. Our results exclude rifamycin O as a common progenitor in the biosyntheses of rifamycins B and L. Rifamycins B and L are formed from rifamycin S (SV) by different pathways using different C3-precursors for the biosynthesis of their glycolic acid moieties. A thiamine-dependent enzyme (decarboxylase) seems to be involved in the transformation reaction.
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III. INCORPORATION OF DL-[3, 4-13C2]GLUTAMIC ACID
S. W. ELSON, R. S. OLIVER, B. W. BYCROFT, E. A. FARUK
1982 Volume 35 Issue 1 Pages
81-86
Published: 1982
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The role of glutamate in clavulanic acid biosynthesis was investigated by feeding DL-[3, 4-
13C
2]glutamate to a
Streptomyces clavuligerus fermentation. The DL-[3, 4-
13C
2]glutamate was synthesised by reacting [2-
13C]diethylmalonate with
O-tosyl-
N-benzoyl-[3-
13C]dehydroserine ethyl ester, which in turn was synthesised by condensing [
13C]ethylformate with
N-benzoylglycine ethyl ester.
13C NMR examination of the benzyl clavulanate derived from the fermentation revealed the predicted labelling of carbons 2 and 8 with accompanying
13C-
13C spin-spin coupling. Other enrichments and couplings were observed which could be explained by metabolism of the labelled glutamate
via the tricarboxylic acid cycle to give further clavulanic acid precursors. These results confirm that glutamate provides the oxazolidine carbon skeleton as predicted by previous experiments.
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KENICHI SHIMIZU, SHUJI OHKUBO, MAKOTO MORIMOTO, FUSAO TOMITA
1982 Volume 35 Issue 1 Pages
87-89
Published: 1982
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KUNIO ATSUMI, EIICHI AKITA, TARO NIIDA
1982 Volume 35 Issue 1 Pages
90-91
Published: 1982
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ANANTA K. DAS, DURLAV K. ROY, B. C. PAL, S. B. MAHATO
1982 Volume 35 Issue 1 Pages
92-93
Published: 1982
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SHIGETO KITAMURA, HIROSHI KASE, YOSHIHIRO ODAKURA, TAKAO IIDA, KUNIKAT ...
1982 Volume 35 Issue 1 Pages
94-97
Published: 1982
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CARLO BATTISTINI, GIOVANNI FRANCESCHI, FRANCO ZARINI, GIUSEPPE CASSINE ...
1982 Volume 35 Issue 1 Pages
98-101
Published: 1982
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KEN-ICHI HARADA, MAKOTO SUZUKI, NAOHITO TAKEDA, AKIRA TATEMATSU, HIDEK ...
1982 Volume 35 Issue 1 Pages
102-105
Published: 1982
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KIYOTO EDO, MIYOKO ITO, NAKAO ISHIDA, YOSHIO KOIDE, AKIRA ITO, MAKOTO ...
1982 Volume 35 Issue 1 Pages
106-110
Published: 1982
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BARNEY J. MAGERLEIN, STEPHEN A. MIZSAK
1982 Volume 35 Issue 1 Pages
111-112
Published: 1982
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AKIHIRO TANAKA, TSUTOMU TSUCHIYA, YUMIKO OKADA, SUMIO UMEZAWA, MASA HA ...
1982 Volume 35 Issue 1 Pages
113-116
Published: 1982
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YOSHIKAZU TAKAHASHI, MITSUHIRO KINOSHITA, TORU MASUDA, KUNIAKI TATSUTA ...
1982 Volume 35 Issue 1 Pages
117-118
Published: 1982
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YOSUKE SAWADA, NANCY L. REICHENBACH, CECIL C. CROSS, ROBERT J. SUHADOL ...
1982 Volume 35 Issue 1 Pages
119-121
Published: 1982
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