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I.TAXONOMY, FERMENTATION, ISOLATION AND CHARACTERIZATION
MICHIO YAMASHITA, YASUHISA TSURUMI, JUNJI HOSODA, TADAAKI KOMORI, MASA ...
1984 Volume 37 Issue 11 Pages
1279-1283
Published: 1984
Released on J-STAGE: April 19, 2006
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A novel antifungal antibiotic, chryscandin was found in the culture broth of a strain of fungi. The producing organism was subsequently identified as
Chrysosporium pannorum. The antibiotic obtained as colorless needle clystals(C
20H
23N
7O
6, MW 457)is active against
Candida albicans and Gram-positive bacteria, but it is ineffective against filamentous fungi and Gram-negative bacteria. Acute toxicity ls very low in mice.
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II. STRUCTURE DETERMINATION AND SYNTHESIS
MICHIO YAMASHITA, YOSHIO KAWAI, ITSUO UCHIDA, TADAAKI KOMORI, MASANOBU ...
1984 Volume 37 Issue 11 Pages
1284-1293
Published: 1984
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The structure of chryscandin, a novel antifungal antibiotic, produced by
Chrysosporium pannorumV No.4629 was deduced to be
1 from spectroscopic and chemical evidences. In order to confirm the structure and to determine the absolute configuration, the total synthesis of chryscandin was performed. D-Xylose was transformed into
10 in ten steps. After β-glycosidation of silylated benzoyl adenine with
10, the resulting
11 was converted into
4, which was identical with the product obtained from chryscandin by alkaline hydrolysis. From the key intermediate
13, chryscandin was synthesized
via peptide formation followed by removal of the protecting groups. Chryscandin(
1)is the first naturally occurring nucleoside antibiotic possessing a 3-aminoribofuranuronlc acid in the molecule.
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KAZUHIKO KINTAKA, HIDEO ONO, SHIGETOSHI TSUBOTANI, SETSUO HARADA, HISA ...
1984 Volume 37 Issue 11 Pages
1294-1300
Published: 1984
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Thiotropocin, a new sulfur-containing 7-membered-ring antibiotic, was isolated from aculture broth of
Pseudomonas sp. CB-104. The antiblotic occurs as orange or yellowish orange needles and has the molecular formula C
8H
4O
3S
2. It is active against Gram-positive and Gram-negative bacteria, some phytopathogens and mycoplasma.
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YUKIHIKO KAMEDA, NAOKI ASANO, MICHIYO YOSHIKAWA, MASAYOSHI TAKEUCHI, T ...
1984 Volume 37 Issue 11 Pages
1301-1307
Published: 1984
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Valiolamine, a new aminocyclitol has been isolated from the fermentation broth of
Streptomyces hygroscopicus subsp. limoneus and its structure has been determined to be (1(OH), 2, 4, 5/1, 3)-5-amino-1-
C-(hydroxymethyl)-1, 2, 3, 4-cyclohexalletetrol. Valiolamine has more potent α-glucosidase inhibitory activity against porcine intestinal sucrase, maltase and isomaltase than valienamine, validamine and hydroxyvalidamine which were reported as building blocks of validamycins and microbial oligosaccharideα-glucosidase inhibitors. In addition, valienamine, validamine and hydroxyvalidamine have been isolated from the fermentation broth.
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I.TAXONOMY, FERMENTATION AND BIOLOGICAL PROPERTIES
KAREN BUSH, PAUL R. HENRY, MARGARET SOUSER-WOEHLEKE, WILLIAM H. TREJO, ...
1984 Volume 37 Issue 11 Pages
1308-1312
Published: 1984
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Phenacein, 3, 6-dihydroxy-1-phenazinecarboxylic acid, was a specific angiotensin-converting enzyme (ACE) inhibitor isolated from a member of the
Streptomyces tanashiensis-zaomyceticus group. Phenacein acted as a pure competitive inhibitor with a
Ki of 0.58μM. ACE inhibition could be reversed by Zn
++, but not by Co
++, Ca
++, or Mg
++; therefore, phenacein may chelate the active site zinc of ACE. However, other zinc-containing enzymes were not inhibited at high phenacein concentrations. Phenacein exhibited weak activity against Gram-positive bacteria, but was not active against
Candida sp. or Gram-negative organisms.
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II. ISOLATION, STRUCTURE DETERMINATION AND SYNTHESIS
WEN-CHIH LIU, WILLIAM L. PARKER, STEVEN S. BRANDT, KARNAIL S. ATWAL, E ...
1984 Volume 37 Issue 11 Pages
1313-1319
Published: 1984
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Phenacein, an inhibitor of angiotensin-converting enzyme, has been isolated from the fermentation broth of a
Streptomyces species belonging to the
Streptomyces tanashiensiszaomyceticus group. The inhibitor was shown to be 3, 6-dihydroxy-1-phenazinecarboxylic acid by spectroscopic, degradative and synthetic methods.
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SHIGEHIRO TAKASE, MORITA IWAMI, TAKESHI ANDO, MASANORI OKAMOTO, KEIZO ...
1984 Volume 37 Issue 11 Pages
1320-1323
Published: 1984
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Amauromine is a new alkaloid with vasodilating activity obtained from the culture broth of
Amauroaucus sp. No.6237. Its molecular formula was determined to be C
32H
35N
46N
4O
2 on the basis of elementary analysis and high resolution mass spectroscopic measurement. It has low toxicity in mice.
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FERMENTATION, ISOLATION, STRUCTURE AND BIOLOGICAL ACTIVITY
SATOSHI OMURA, MASATSUNE MURATA, NOBUTAKA IMAMURA, YUZURU IWAI, HARUO ...
1984 Volume 37 Issue 11 Pages
1324-1332
Published: 1984
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A new amino acid-antimetabolite, oxetin, was isolated from a fermetation broth of a
Streptomycesp .s OM-2317, a soil isolate, The chemical structure was elucidated as(2
R, 3
S)-3-amino-2-oxetane carboxylic acid by analysis of the spectral data and by X-ray diffraction methods. The antibiotic is the first natural product possessing an oxetane ring. Certain microorganisms were inhibited by oxetin only when cultivated in minimal media. The inhibitory action was reversed by several amino acids such as L-isoleucine, L-methionine, L-valine and L-glutamine. It also exhibited herbicidal activity and inhibited glutamine synthetase from spinach leaves.
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HARUYASU KINASHI, KINUMI SOMENO, KENJI SAKAGUCHI
1984 Volume 37 Issue 11 Pages
1333-1343
Published: 1984
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Concanamycins A, B and C were isolated from the mycelium of
Streptomyces diastatochromogenes S-45 as effective inhibitors of the proliferation of mouse splenic lymphocytes stimulated by concanavalin A. They represent a new class of 18-membered macrolide antibiotics, and are biologically active in vitro against several fungi and yeasts, but not against bacteria. Concanamycin A, the main component, has been identified with antifungal antibiotics, folimycin and A-661-I.
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SYLVIA K. GONDA, KEVIN M. BYRNE, PATRICIA K. HERBER, YVES TONDEUR, DAN ...
1984 Volume 37 Issue 11 Pages
1344-1356
Published: 1984
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Largomycin FII, a protein antitumor antibiotic of molecular weight 29, 300 daltons, contains a chromophore that is separable under mild denaturing conditions. The chromophore complex was found to be considerably less stable than the holoprotein towards light and heat, suggesting a protective effeect of the protein on the chromophore. Separation of the chromophore into several components was achieved using high performance liquid chromatography, and the biological activity of the isolated components was determined. Data gathered from UV, IR, proton and carbon NMR, and fast atom bombardment mass spectrometry indicated that all the chromophore components belong to the pluramycin class of antitumor agents. Pluramycin A and deacetylpluramycin A were found to be the two major components.
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ABSOLUTE CONFIGURATION OF NAPHTHOMYCIN A DETERMINED BY X-RAY ANALYSIS AND CHEMICAL DEGRADATION
WALTER KELLER-SCHIERLEIN, MICHAEL MEYER, LUCIANO CELLAI, SILVIO CERRIN ...
1984 Volume 37 Issue 11 Pages
1357-1361
Published: 1984
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The relative and absolute configurations of naphthomycin A were elucidated by an X-ray structural analysis of a methylation product, 25-
O-methylnaphthomycin A iminomethyl ether. The absolute configuratlon was confirmed by degradation(O
3, NaBH
4)to(
S)-butane-1, 2, 4-triol.
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SATOSHI OMURA, ARIHIRO TAKI, KAZUKI MATSUDA, YOSHITAKE TANAKA
1984 Volume 37 Issue 11 Pages
1362-1369
Published: 1984
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Protylonolide is a lactonic precursor of tylosin aglycone, produced by a mutant of
Streptomyces. fradiae It originates from
n-butyrate, propionate and acetate units. Studies were carried out using a protylonolide-producing mutant on the correlation between protylonolide biosynthesis, regulation by NH
4+ and amino acid metabolism. Protylonolide production decreased in a defined medium containing high levels of NH
4+, but was restored by adding lower fatty acids expected to serve as precursors of protylonolide biosynthesis. Resting cell studies demonstrated that
14C-labeled valine threonine leucine isoleucine and alanine but not lysine, were efficiently incorporated into protylonolide, indicating that these amino acids are metabolized to lower fatty acids. The incorporation of amino acids into protylonolide was reduced when the mutant strain was previously grown under high NH
4+ conditions. We suggest that NH
4+ suppresses the relevant amino acid metabolism, thereby reducing protylonolide formation.
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YOSHITAKE TANAKA, ROKURO MASUMA, SATOSHI OMURA
1984 Volume 37 Issue 11 Pages
1370-1375
Published: 1984
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The addition of a small amount of NH
4+ to a complex medium increased nanaomycin production by
Streptomyces rosa subsp. notoensis OS-3966. The best NH
4+ domor for nanaomycin production was NH
4+-saturated natural zeolite, with which the maximum titer of nanaomycin E was 760μg/ml, about four fold higher than the control titer. In contrast, lowering NH
4+ levels by adding NH
4+-trapping agents such as untreated natural zeolite reduced antibiotic production.
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JOHN M. BEALE, Jr., ROBERT L. CHAPMAN, JOHN P. N. ROSAZZA
1984 Volume 37 Issue 11 Pages
1376-1381
Published: 1984
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The biosynthesis of terrecyclic acid A was investigated using
13C-1abeled acetates and mevalonate.
13C NMR spectral analysis of isolated labeled terrecyclic acid demonstrated that the structure is assembled via an isoprene pathway.
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H.-R. TSOU, R. R. FIALA, P. C. MOWERY, M. W. BULLOCK
1984 Volume 37 Issue 11 Pages
1382-1387
Published: 1984
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The biosynthesis of the spermidine and guanidino groups has been studied with carbon-14 and carbon-13 labeled intermediates. Arginine, citrulline and ornithine are incorporated in good efficiency. The guanidino group of arginine and the ureido group of citrulline both label the guanidino group on the hexose sugar. None of the ureido groups in the antibiotic was enriched. It is likely that citrulline is converted to arginine before use in the biosynthesis. Arginine, citrulline and ornithine are incorporated as the four carbon unit of spermidine. All of the labeled 5 carbon from ornithine or from citrulline appears adjacent to the secondary amine in the four carbon unit of spermidine. This would indicate that unbound putrescine is not an immediate precursor of spermidine.
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I. BIOSYNTHETIC SIGNIFICANCE OF THE OA-6129 GROUP OF CARBAPENEM COMPOUNDS AS THE DIRECT PRECURSORS FOR PS-5, EPITHIENAMYCINS A AND C AND MM 17880
YASUO FUKAGAWA, MITSUYASU OKABE, SHOJI AZUMA, IKUO KOJIMA, TOMOYUKI IS ...
1984 Volume 37 Issue 11 Pages
1388-1393
Published: 1984
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Based on the working hypothesis that the OA-6129 group of carbapenem compounds might be the direct precursors for PS-5, epithienamycins A and C and MM 17880,
Streptomyces fulvoviridis A93317M9, a producer of PS-5, PS-6, PS-7, PS-8, epithienamycins A, B, Cand D, MM 17880, MM 13902 and MM 4550, was subjected to NTG-mutation to provide ablocked mutant numbered 1501 which was found to produce OA-6129A, OA-6129B
1, OA-6129B
2 and OA-6129C instead of PS-5, epithienamycins A and C and MM 17880, respectively. In a cell-free system, the parent strain demonstrated an ability to collvert OA-6129A to NS-5, whereas the mutant did not. The L-and D-amino acid acylases were also shown to depantothenylate the OA-6129 group of carbapenems.
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II. ISOLATION AND FUNCTIONS OF A SPECIFIC ACYLASE INVOLVED IN THE DEPANTOTHENYLATION OF THE OA-6129 COMPOUNDS
KATSURO KUBO, TOMOYUKI ISHIKURA, YASUO FUKAGAWA
1984 Volume 37 Issue 11 Pages
1394-1402
Published: 1984
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A specific acylase designated A933 acylase was isolated and purified to 90% protein homogeneity from
Streptomyces fulvoviridis A933 17M9 which produces PS-5, epithienamycins A and C and MM 17880 together with minor carbapenem analogs, penicillin N and cephamycin C. This enzyme was found to catalyze the depantothenylation of OA-6129 carbapenems; the acyl exchange of OA-6129 carbapenems with acyl CoA's; the deacetylation of
N-acetyl-L-amino acids; and the acylation of NS-5 and 6-aminopenicillanate with acyl CoA's, whereas the deacetylation of PS-5 and
N-acetyl-D-amino acids; and the deacylation of benzylpenicillin and cephalosporin C were not observed. Similar enzyme activities were also detected in
Streptomyces cattleya, Streptomyces cremeus subsp.
auratilis and Streptomyces argenteolus which are all carbapenem producers.
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SHIGEHARU INOUYE, TSUTOMU TSURUOKA, HITOSHI GOI, KATSUYOSHI IWAMATSU, ...
1984 Volume 37 Issue 11 Pages
1403-1413
Published: 1984
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The effect of chemical modification of the D-amino acid function, which represents the C-7βsubstituent of cephamycin MT-141 on
in vitro antibacterial activity was examined. MT-141 was more active on Gram-negative organisms than Gram-positive ones. It showed strong bacteriolytic activity on Gram-negative organisms. Lysis of
Escherichia coli K-12 strain JE1O11 treated with a low concentration of this antibiotic was preceded by frequent formation of multiple bulges from the cells. Amidation or decarboxylation, removing the acidic function from the D-amino acid of MT-141, resulted in an increase in activity against Gram-positive bacteria, and a decrease against Gram-negative ones. Cells treated with the amide or the decarboxylate did not form multiple bulges but formed single bulges.
N-Acetylation of the D-amino acid moiety removing the basic function, caused a marked drop in activity against both Gram-positive and Gram-negative bacteria. The bacteriolytic activity on
E. coli. was reduced and cells treated with the
N-acetate became filamentous Conversion of the D-amino acid function of MT-141 to the L configuration caused a moderate drop in activity against both Gram-positive and Gram-negative organisms. Both bacteriolytic and bactericidal activities against
E. coli were reduced in the L-congener. Cefoxitin, cefmetazole and latamoxef used as reference antibiotics were less active than MT-141 in the bactericidal activity against
E. coli. and induced single bulge formation or filamentation of the cells around MIC levels. Cell-surface permeability, stability to β-lactamases, and binding affinity to PBPs of
E. coli. did not differ between MT-141 and its derivatives.
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MICHIKO SAKAMOTO, TOMOYUKI ISHIKURA, YASUO FUKAGAWA
1984 Volume 37 Issue 11 Pages
1414-1422
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The
in vitro synergism or PS-5 combined with various penicinins and cephalosporins in antimicrobial activity was examined in detail against β-lactam-resistant Gram-negative bacteria. PS-5 showed a highly significant synergism in antimicrobial action against
Escherichia coli RGN238 in combination with penicinins; and against
Proteus vulgaris GN76 and
Serratia marcescens T55 in combination with cephalosporins. It was moderately synergistic against
Citrobacter freundii GN346,
Enterobacter cloacae 45,
Proteus morganii 111 and
Enterobacter aerogenes E19, whereas no synergism was observed against
Pseudomonas aeruginosa E2 and
Klebsiella pneumoniae. 130
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SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF NEW CEPHALOSPORINS BEARING A 2-IMINO-3-HYDROXYTHIAZOLINE (2-AMINOTHIAZOLE N-OXIDE) IN THE C-7 ACYLAMINO SIDE CHAIN
ETTORE PERRONE, MARCO ALPEGIANI, FRANCO GIUDICI, FRANCO BUZZETTI, GIUL ...
1984 Volume 37 Issue 11 Pages
1423-1440
Published: 1984
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Introduction of a hydroxyl group into the thiazole ring nitrogen of cephalosporins belonging to the cefotiam and cefotaxime families gave rise to products, better described by the tautomeric
N-oxide form, which proved particularly active against Gram-negative bacteria. Cephems bearing a(
Z)-alkoxyimino functionality are of special interest for broadness of spectrum; among them, 7β-[(
Z)2-(2-amino-4-thiazolyl-
N-oxide)-2-methoxyiminoacetanlido]-3-(tetrazolo-[1, 5-b]pyridazin-6-yl)thiomethyl-3-cephem-4-carboxylic acid (5c-7, FCE 20635), in other ways similar to cefotaxime, showed useful levels of activity against cephalosporinase-producing strains resistant to the reference drug. Preliminary
in vivo studies demonstrated the therapeutic efficacy of the new compound in the treatment of experimental systemic, subcutaneous and urinary tract infections in mice.
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JOHN C. SHEEHAN, ELSIE CHACKO, THOMAS J. COMMONS, YOUNG S. LO, DAGMAR ...
1984 Volume 37 Issue 11 Pages
1441-1448
Published: 1984
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Antibiotic and penicillinase inhibitor activities of various penicillin and cephalosporin analogs are reported. The compounds include C-6 penicillin and C-7 cephalosporin carbon, oxygen and sulfur analogs obtained by replacing the NH of the amide side chains with CH
2, O and S, respectively. In almost all cases, analogs were considerably less active than the standard compounds (benzylpenicillin and cephalothin), However, some of the analogs act as penicillinae inhibitors.
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SHOJI SHIMA, HIROYOSHI MATSUOKA, TOSHIRO IWAMOTO, HEIICHI SAKAI
1984 Volume 37 Issue 11 Pages
1449-1455
Published: 1984
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The antimicrobial spectrum of ε-poly-L-lysine (n=25-30, ε-PL) was investigated by comparison with α-poly-L-lysine (n=50, α-PL). ε-PL showed antimicrobial activity against Gram-positive and-negative bacteria at concentrations of 1-8μg/ml. α-PL was less active than ε-PL A chain length of at least 10 L-lysine monomers was found to be optimum for antimicrobial activity. Chemical modification of the amino groups of ε-PL lowered its antibacterial activity. Studies on the mode of action of ε-PL suggest that adsorption of ε-PL to the bacterial cell surface plays an important role in its antibacterial activity.
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TOSHIAKI HAYASHI, OSAMI YAMAMOTO, HIROSHI SASAKI, HIROSHI OKAZAKI, AKI ...
1984 Volume 37 Issue 11 Pages
1456-1461
Published: 1984
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The antibiotic thiolactomycin inhibits the growth of
Escherichia coli K-12 and
Pseudomonas aeruginosa 507 (β-lactam supersensitive mutant). A micrograph of
E. coli cells, which were grown at a sublethal concentration of thiolactomycin (20μg/ml), revealed the morphological change with cell elongation. The effects of the antibiotic on syntheses of cellular constituents were studied by measuring the incorporation of labeled precursors into lipids and macromolecules. This antibiotic preferentially inhibited the incorporation. of [
14C] acetate into fatty acids and lipids. Addition of both palmitate and oleate, but not of either fatty acid alone, reversed the growth inhibition of
P. aeruginosa by thiolactomycin. These findings support the conclusion that the effects of thiolactomycin are due to a specific inhibition of fatty acid synthetase.
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RAYMOND C. YAO, DAVID F. MAHONEY
1984 Volume 37 Issue 11 Pages
1462-1468
Published: 1984
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A heterogeneous microplate enzyme immunoassay with a sensitivity of 10 pg/ml (1 pg/assay) toward gentamicin has been developed for the detection of aminoglycoside antibiotics in fermentation broths. Purified gentamicin antibody was coated onto the surface of the wells of microtiter plates and incubated with gentamicin-alkaline phosphatase conjugate. The amount of enzyme bound to the antibody was quantified by measuring the change in absorbance at 410 nm after the addition of the substrate,
p-nitrophenylphosphate. Competitive assays performed by incubating the antibody and enzyme conjugate with various aminoglycosides showed that the antibody probe cross-reacted with aminoglycosides tested, except neomycins B and C. No cross-reaction was detected with non-aminoglycoside antibiotics. Complex fermentation broths did not interfere with this assay. Cultures known to produce aminoglycosides were detected at levels well below the concentrations required for antimicrobial activity. This technique is useful in the identification, quantification and screening of fermentation metabolites.
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III. GLYCOSIDATION OF NATURAL AND CHEMICALLY SYNTHESIZED ANTHRACYCLINE AGLYCONES
TATSUO HOSHINO, YUTAKIA SETOGUCHI, AKIKO FUJIWARA
1984 Volume 37 Issue 11 Pages
1469-1472
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IV. STUDY ON THE GLYCOSIDATION OF ε-PYRROMYCINONE BY STREPTOMYCES GALILAEUS OBB-111-848
TATSUO HOSHINO, AKIKO FUJIWARA
1984 Volume 37 Issue 11 Pages
1473-1474
Published: 1984
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JOEL HENNER, ROBERT D. SITRIN
1984 Volume 37 Issue 11 Pages
1475-1478
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RYSZARD ANDRSUZKIEWICZ, HENRYK CHMARA, EDWARD BOROWSKI
1984 Volume 37 Issue 11 Pages
1479-1482
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AKIRA YOTSUJI, SHINZABUROU MINAMI, SEIKI OKAMOTO, TAKASHI YASUDA, AKIR ...
1984 Volume 37 Issue 11 Pages
1483-1485
Published: 1984
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JUN'ICHI SHOJI, TOSHIYUKI KATO, RYUZI SAKAZAKI, WATARU NAGATA, YOSHIHI ...
1984 Volume 37 Issue 11 Pages
1486-1490
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SHUICHI GOMI, DAISHIRO IKEDA, HIKARU NAKAMURA, HIROSHI NAGANAWA, FUMIO ...
1984 Volume 37 Issue 11 Pages
1491-1494
Published: 1984
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SRINIVASAN RAJAN, HWEI-RU TSOU, PATRICK C. MOWERY, MILON W. BULLOCK, G ...
1984 Volume 37 Issue 11 Pages
1495-1500
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HEATHER A. BROOKS, DONALD GARDNER, J. PHILIP POYSER, TREVOR J. KING
1984 Volume 37 Issue 11 Pages
1501-1504
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4. PRODUCTION OF PHOSPHONIC ACID DERIVATIVES, 2-HYDROXYETHYLPHOSPHONIC ACID, HYDROXYMETHYLPHOSPHONIC ACID AND PHOSPHONOFORMIC ACID BY BLOCKED MUTANTS OF STREPTOMYCES HYGROSCOPICUS SF-1293 AND THEIR ROLES IN THE BIOSYNTHESIS OF BIALAPHOS1)
SATOSHI IMAI, HARUO SETO, TORU SASAKI, TAKASHI TSURUOKA, HIROSHI OGAWA ...
1984 Volume 37 Issue 11 Pages
1505-1508
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5. PRODUCTION OF 2-PHOSPHINOMETHYLMALIC ACID, AN ANALOGUE OF CITRIC ACID BY STREPTOMYCES HYGROSCOPICUS SF-1293 AND ITS INVOLVEMENT IN THE BIOSYNTHESIS OF BIALAPHOS1)
HARUO SETO, SATOSHI IMAI, TORU SASAKI, KUMIKO SHIMOTOHNO, TAKASHI TSUR ...
1984 Volume 37 Issue 11 Pages
1509-1511
Published: 1984
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