Papers by Tatsuo Haneishi
ACS Symposium series. American Chemical Society, 1994
The Journal of Antibiotics, 1987
Chloropolysporins A, B and C, new membersof the glycopeptide antibiotic family, wereenzymatically... more Chloropolysporins A, B and C, new membersof the glycopeptide antibiotic family, wereenzymatically and chemically converted to their partially deglycosylated derivatives. The a-and /3-avoparcins werealso deglycosylated by the samemethod. The conversions were achieved by treatments with rhamnosidase (Naringinase) and a-mannosidase, and by mild acid hydrolysis. In the previous papers1"3-*, we described the taxonomy of the producing organism, isolation,
The Journal of Antibiotics, 1987
Strain SANK 60983, an actinomycete isolated from a soil sample, was found to produce the new glyc... more Strain SANK 60983, an actinomycete isolated from a soil sample, was found to produce the new glycopeptide antibiotics, chloropolysporins A, B and C. Short chains of spores occur in the both aerial and substrate hyphae. meso-Diaminopimelic acid is present in the cell wall and galactose and arabinose in the whole-cell hydrolysate. Mycolic acid is absent. On the basis of the morphological, cultural and physiological characteristics, this strain was determined to be a new species of Faenia designated Faenia interjecta sp. nov. The type strain of F. interjecta Okazaki and Enokita is SANK60983. In the course of an extensive screening program for new antibiotics produced by rare actinomycetes, new antibiotics, chloropolysporins, were discovered in our laboratories. This paper deals with the taxonomy of the producing organism. Fermentation, isolation, physico-chemical characterization and structure elucidation as well as biological properties of the antibiotics will be described in subsequent papers. Materials and Methods Actinomycete Strain Strain SANK60983 was isolated from a soil sample collected at Kuroiso, Tochigi Prefecture, Japan. One drop of the water suspension of the soil sample was plated on the surface of NH4Cl-glycerol agar medium consisting of glycerol 1.5 %, NH4C1 0.2%, CaCO3 0.1 %, K2HPO4 0.05 %, MgSO4-7H2O 0.5%, FeSO4-7H2O 0.001 % and agar 2.0% at pH 7.0 before sterilization. The plate was incubated at 28°C for 10 days. The strain SANK60983 was inoculated into International Streptomyces Project (ISP) medium 1 in a Sakaguchi flask and grown for 3 days at 28°C on a reciprocal shaker. After harvesting by centrifugation, the culture was washed twice with sterile distilled water by centrifugation, and then used as inoculum for various studies. In addition to the ISP media described by Shirling and Gottlieb0, several agar media recommendedby Waksman2) were also used in this study. Morphological Characterization The spore chain morphology and the hyphae of the strain grown on various agar media at 28°C for 14~21 days were determined with a light microscope. A sample, treated with a critical point dryer (HCP-1 , Hitachi Co., Ltd.) after stepwise dehydration by ethanol, was observed under an MSM-6 scanning electron microscope (Akashi Seisakusho Co., Ltd.). Cultural Characterization Observation of the growth on various agar media was made after incubation at 28°C for 14 days unless otherwise mentioned. The mass colors of the growth were assigned in commonterminology. Micropolyspora interjecta SANK60983 (FERM BP-538).
The Journal of Antibiotics, 1987
Strain SANK 60983, an actinomycete isolated from a soil sample, was found to produce the new glyc... more Strain SANK 60983, an actinomycete isolated from a soil sample, was found to produce the new glycopeptide antibiotics, chloropolysporins A, B and C. Short chains of spores occur in the both aerial and substrate hyphae. meso-Diaminopimelic acid is present in the cell wall and galactose and arabinose in the whole-cell hydrolysate. Mycolic acid is absent. On the basis of the morphological, cultural and physiological characteristics, this strain was determined to be a new species of Faenia designated Faenia interjecta sp. nov. The type strain of F. interjecta Okazaki and Enokita is SANK60983. In the course of an extensive screening program for new antibiotics produced by rare actinomycetes, new antibiotics, chloropolysporins, were discovered in our laboratories. This paper deals with the taxonomy of the producing organism. Fermentation, isolation, physico-chemical characterization and structure elucidation as well as biological properties of the antibiotics will be described in subsequent papers. Materials and Methods Actinomycete Strain Strain SANK60983 was isolated from a soil sample collected at Kuroiso, Tochigi Prefecture, Japan. One drop of the water suspension of the soil sample was plated on the surface of NH4Cl-glycerol agar medium consisting of glycerol 1.5 %, NH4C1 0.2%, CaCO3 0.1 %, K2HPO4 0.05 %, MgSO4-7H2O 0.5%, FeSO4-7H2O 0.001 % and agar 2.0% at pH 7.0 before sterilization. The plate was incubated at 28°C for 10 days. The strain SANK60983 was inoculated into International Streptomyces Project (ISP) medium 1 in a Sakaguchi flask and grown for 3 days at 28°C on a reciprocal shaker. After harvesting by centrifugation, the culture was washed twice with sterile distilled water by centrifugation, and then used as inoculum for various studies. In addition to the ISP media described by Shirling and Gottlieb0, several agar media recommendedby Waksman2) were also used in this study. Morphological Characterization The spore chain morphology and the hyphae of the strain grown on various agar media at 28°C for 14~21 days were determined with a light microscope. A sample, treated with a critical point dryer (HCP-1 , Hitachi Co., Ltd.) after stepwise dehydration by ethanol, was observed under an MSM-6 scanning electron microscope (Akashi Seisakusho Co., Ltd.). Cultural Characterization Observation of the growth on various agar media was made after incubation at 28°C for 14 days unless otherwise mentioned. The mass colors of the growth were assigned in commonterminology. Micropolyspora interjecta SANK60983 (FERM BP-538).
The Journal of Antibiotics, 1983
The structure of mycoplanecin A was determined by the analysis of chemical degradation products a... more The structure of mycoplanecin A was determined by the analysis of chemical degradation products and by mass and 1H and 13C NMR spectrometries. Mycoplanecin A is a new cyclic peptide antibiotic composed of mol each of a-ketobutyric acid, glycine, L-leucine, L-proline, L-2-amino-5-methylhexanoic acid, N-methyl-n-leucine, Nmethyl-L-threonine, methyl-L-proline and ethyl-L-proline and two mol of N-methyl-L-valine. Among these components, ethyl-L-proline is reported for the first time as a component of natural products. A newly developed mass analysis has been introduced for the differentiation of a-amino acid and its N-methyl derivative.
Chemischer Informationsdienst, Feb 17, 1981
Journal of the Chemical Society, 1991
The structure of a novel herbicide, hydantocidin isolated from the fermentation broth of Streptom... more The structure of a novel herbicide, hydantocidin isolated from the fermentation broth of Streptomyces hygroscopics SANK 63584, was determined by the combined analysis of MS and 1H NMR spectra. Hydantocidin is a novel spiro compound containing a subofuranoid ring, at the anomeric position of which a hydantoin ring is used such that the C(1)–N(1) linkage is β. The relative configuration and the conformation in solution was determined by quantitative analysis of the NOE spectra and T1 values. In CD3OD and [2H6]DMSO (dimethyl sulphoxide) solutions, the ribofuranose moiety of hydantocidin was found to be fixed in a C2-endo conformation, probably due to the rigidity of the spiro structure and hydrogen bonding between 3-OH and the carbonyl group at C-4′.
ChemInform, Aug 22, 2010
The 2-O-benzylribofuranosyl fluorides (I) and (III) undergo Lewis acid-catalyzed cyclization, for... more The 2-O-benzylribofuranosyl fluorides (I) and (III) undergo Lewis acid-catalyzed cyclization, forming the fused isochromans (II) or (IV). Hydrogenation of (II), followed by acetylation, produces the triacetoxypropylisochroman (VI).
The Journal of Antibiotics, 1987
Structure elucidations of chloropolysporins A, B and C were achieved mainly by chemical degradati... more Structure elucidations of chloropolysporins A, B and C were achieved mainly by chemical degradation studies. These componentspossessed the same pseudoaglycone in common and their structures were closely related to that of /3-avoparcin. The structures of chloropolysporins differ from that of /J-avoparcin in the presence of vancomycinic acid moiety instead of monodechlorovancomycinic acid moiety and glucose, not ristosaminylglucose, in its side chain. Chloropolysporin C was identified as derhamnosylchloropolysporin B based on its XHNMR and mass spectral analysis and degradation studies. Twominor components, chloropolysporins D and E, were identified as the epimers of each of chloropolysporins B and C, respectively, based on their Cotton effects and retention times on reverse phase HPLC Chloropolysporins A, B and C are new membersof the glycopeptide antibiotics produced by Faenia interjecta sp. nov. SANK60983. Taxonomy of the producing organism^, fermentation, isolation and physico-chemical characterization50 of chloropolysporins were reported in the preceding
Accounts of Chemical Research, 2001
Twenty years ago, one of us embarked (Bursill, L. A.; Lodge, E. A.; Thomas, J. M. Zeolitic struct... more Twenty years ago, one of us embarked (Bursill, L. A.; Lodge, E. A.; Thomas, J. M. Zeolitic structures as revealed by high-resolution electron microscopy. Nature 1980, 286, 111-113) on the study of zeolites (renowned for their electron-beam sensitivity) by highresolution transmission electron microscopy (HRTEM). In the ensuing years, high-resolution imaging aided by optical diffractometry has yielded details of the open framework structures of a number of new aluminosilicate and aluminophosphate molecular sieves and catalysts. The nature of intergrowth and recurrently twinned structures, as well as new types of structural imperfection in hitherto uncharacterized materials, has also been elucidated. With continued improvements in instrumental development, encompassing higher accelerating voltages, better objective lenses and vacua, computational advances, and the arrival of slow-scan CCD detectors, electron crystallographic methods and HRTEM imaging now enable the ab initio three-dimensional structures of micro-and mesoporous solids, with their occluded structuredirecting organic species, to be determined. High-resolution scanning transmission electron microscopy using subnanometric probes provides supplementary structural and ultramicro analytical information and electron spectroscopic imaging (at the attogram level). In its high-angle annular dark-field mode, it is capable of locating and determining the composition of individual nanoparticle catalysts (consisting of just a few atoms) supported on porous hosts.
The Journal of antibiotics, 1974
Antimicrobial Agents and Chemotherapy, 1988
The in vitro activity of dihydromycoplanecin A (DHMP A), a new cyclic peptide antibiotic, was com... more The in vitro activity of dihydromycoplanecin A (DHMP A), a new cyclic peptide antibiotic, was compared with those of antimycobacterial drugs such as streptomycin, isoniazid (INH), rifampin, and ofloxacin against several clinically isolated species of mycobacteria, including Mycobacterium tuberculosis, M. intracellulare, and M. kansasii. DHMP A demonstrated stronger activities than other drugs against all species of mycobacteria tested at concentrations of less than 0.0125 to 25 microgram/ml. A marked synergism between DHMP A and INH was demonstrated by the checkerboard technique against M. tuberculosis, M. intracellulare, and M. smegmatis, and the synergistic effect was observed by treatment of the culture of M. smegmatis with DHMP A for at least 3 h prior to treatment with INH. It was also shown that both absorption and excretion of INH in mice were faster than those of DHMP A. On the basis of these results, combination therapy with DHMP A and INH was successfully carried out in ex...
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Papers by Tatsuo Haneishi