| 1.Research Institution | The University of Tokyo | |
| 2.Research Area | Integrated Fields | |
| 3.Research Field | Production of Novel Useful Substances through Integration of Life Sciences and Chemistry | |
| 4.Term of Project | FY1996〜FY2000 | |
| 5.Project Number | 96I00301 | |
| 6.Title of Project | Production of Bioactive Natural Products, and Analysis and Application of its Molecular Mechanism of Biosynthetic Engineering |
| Name | Institution,Department | Title of Position |
| Hayakawa, Yoichi | The University of Tokyo, Institute of Molecular and Cellular Biosciences | Associate Professor |
8.Core Members
| Names | Institution,Department | Title of Position |
| Sakuda, Shohei | The University of Tokyo, Department of Applied Biological Chemistry | Associate Professor |
| Matsunaga, Shigeki | The University of Tokyo, Department of Aquatic Biosciences | Associate Professor |
9.Cooperating Researchers
| Names | Institution,Department | Title of Position |
| Murata, Michio | Osaka University, Department of Chemistry | Professor |
| Ojika, Hajime | Nagoya University, Department of Applied Biological Sciences | Associate Professor |
| Murakami, Masahiro | The University of Tokyo, Department of Aquatic Bioscience | Associate Professor |
10.Summary of Research Results
|
This project consists of two main research themes: (1) screening of novel bioactive compounds among microbial and marine natural products using new bioassay systems, 2) accumulation of basic information on molecular mechanisms of secondary metabolite production in a variety of organisms, and its application to biosynthetic engineering. By the research concerning the former theme, we have succeeded in isolation of a lot of novel bioactive compounds such as apoptosis inducers, neuronal cell protecting substances, substances with TGF-β like activity, DNA topoisomerase I inhibitors, Na, K-ATPase inhibitors, glucosidase inhibitors, protease inhibitors or mycotoxin production inhibitors. These new substances are very important not only for developing useful drugs, but also as bioprobes to investigate molecular mechanisms of unknown biological phenomena. And genes responsible for their biosynthesis are very useful resources for production of useful compounds by biosynthetic engineering. In the latter part, we got very important information on terpenoid biosynthesis, mycotoxin production and biosynthetic mechanism of marine natural products. Especially, in the work on the non-mevalonate pathway for terpenoid biosynthesis, we have succeeded in characterization of several key intermediates, biosynthetic enzymes and genes encoding the enzymes involved in the pathway for the first time in the world. And we have investigated the regulatory mechanism for mycotoxin production by fungi. The information on molecular mechanisms of secondary metabolites obtained by this research may strongly activate a lot of research fields in life sciences, especially the field of biosynthetic engineering important in future. |
11.Key Words
(1)Bioactive Compounds、(2)Biosynthetic Engineering、(3)Terpenoids
(4)Non-mevalonate Pathway、(5)Microbial Secondary Metabolites、(6)Marine Secondary Metabolites
(7)Mycotoxin、(8)Apoptosis Inducer、(9)Telomerase Inhibitor
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| K. Konoki | Direct observation of binding between biotinylated okadaic acid and protein phosphatase 2A monitored by surface plasmon resonance. | |||
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| N. Matsumori | Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants -A method of configuration analysis for natural products. | |||
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| K. Konoki | Development of biotin-Avidin technology to investigate okadaic acid-promoted cell signaling pathway. | |||
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| Tetrahedron | 56 | 2000 | 9003-9014 | |
| Author | Title of Article | |||
| K. Akasaka | Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate, Coolia monotis. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotech. Biochem. | 64 | 2000 | 1842 | |
| Author | Title of Article | |||
| M. Murata | The Structure elucidation and biological activities of high molecular weight algal toxins: maitotoxin, prymnesins and zooxanthellatoxins. | |||
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| Nat. Prod. Rep. | 17 | 2000 | 293-316 | |
| Author | Title of Article | |||
| M. Murakami | A cyclic peptide, anabaenopeptin B, from the cyanobacterium Oscillatoria agardhii. | |||
| Journal | Volume | Year | Pages Concerned | |
| Phytochemistry | 44 | 1997 | 449-452 | |
| Author | Title of Article | |||
| H. J. Shin | Anabaenopeptins C and D, two new cyclic peptides from the cyanobacterium Oscillatoria agardhii (NIES-204). | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Nat. Prod. | 60 | 1997 | 139-141 | |
| Author | Title of Article | |||
| H. J. Shin | Aeruginosins 205-A and B, serine protease inhibitory glycopeptides from the cyanobacterium Oscillatoria agardhii (NIES-205). | |||
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| J. Org. Chem. | 62 | 1997 | 1810-1813 | |
| Author | Title of Article | |||
| K. Ishida | Kawaguchipeptin B, an antimicrobial cyclic undecapeptide from the cyanobacterium Microcystis aeruginosa (NIES-88). | |||
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| K. Ishida | Microginins 299-A and -B, leucine aminopeptidase inhibitors from the cyanobacterium Microcystis aeruginosa (NIES-299). | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron | 53 | 1997 | 10281-10288 | |
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| J. L. Rios | Structure of thrombin inhibited by aeruginosin 298-A from a blue-green alga. | |||
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| B. Sandler | Atomic structure of the trypsin-aeruginosin 98-B complex. | |||
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| J. Am. Chem. Soc. | 120 | 1998 | 595-596 | |
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| S. Kodani | Dehydroradiosumin, a trypsin inhibitor from the cyanobacterium Anabaena cylindrica. | |||
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| J. Natl. Prod. | 61 | 1998 | 854-856 | |
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| S. Kodani, | Aeruginosin 103-A, a thrombin inhibitor from the cyanobacterium Microcystis viridis. | |||
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| J. Natl. Prod. | 61 | 1998 | 1046-1048 | |
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| K. Ishida | Four new microginins, linear peptides from the cyanobacterium Microcystis aeruginosa. | |||
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| Tetrahedron | 54 | 1998 | 13457-13464 | |
| Author | Title of Article | |||
| Y. Itou | Anabaenopeptins G and H, potent carboxypeptidase A inhibitors from the cyanobacterium Oscillatoria agardhii. | |||
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| Bioorg. Med. Chem. Lett. | 9 | 1999 | 1243-1246 | |
| Author | Title of Article | |||
| K. Ishida, | Aeruginosins, protease inhibitors from the cyanobacterium Microcystis aeruginosa, | |||
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| Tetrahedron | 55 | 1999 | 10971-10988 | |
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| S. Kodani | Five new cyanobacterial peptides from water bloom materials of Lake Teganuma. | |||
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| FEMS Microb. Lett. | 178 | 1999 | 343-348 | |
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| M. Murakami | New anabaenopeptins, potent carboxypeptidase-A Inhibitors from the cyanobacterium Ahanizomenon flos-aquae. | |||
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| M. Izumikawa | 18O-labelling pattern of okadaic Acid from H218O in dinoflagellate Prorocentrum lima elucidated by tandem mass spectrometry. | |||
| Journal | Volume | Year | Pages Concerned | |
| Eur. J. Biochem. | 267 | 2000 | 5179-5182 | |
| Author | Title of Article | |||
| K. Ishida | Kasumigamide an antialgal peptide from the cyanobacterium Microcystis aeruginosa. | |||
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| J. Org. Chem. | 65 | 2000 | 5898-5900 | |
| Author | Title of Article | |||
| K. Ishida | Microginins, zinc metalloproteases inhibitors from the cyanobacterium Microcystis aeruginosa. | |||
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| Tetrahedron | 56 | 2000 | 8643-8656 | |
| Author | Title of Article | |||
| M. Ojika | Novel Ceramide 1-Sulfates, Potent DNA Topoisomerase I Inhibitors Isolated from the Bryozoa Watersipora cucullata. | |||
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| Tetrahedron Lett. | 38 | 1997 | 4235-4238 | |
| Author | Title of Article | |||
| T. Nemoto | Amphimic Acids, Novel Unsaturated C28 Fatty Acids as DNA Topoisomerase I Inhibitors from an Australian Sponge Amphimedon sp. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 38 | 1997 | 5667-5670 | |
| Author | Title of Article | |||
| T. Nemoto | Amphimic Acids and Related Long-chain Fatty Acids as DNA Topoisomerase I Inhibitors from an Australian Sponge Amphimedon sp. : Isolation, Structure, Synthesis, and Biological Evaluation. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron | 53 | 1997 | 16699-16710 | |
| Author | Title of Article | |||
| Y. Okamoto | Iantheran A, a Dimeric Polybrominated Benzofuran as a Na, K-ATPase Inhibitor from a Marine Sponge, Ianthella sp. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 40 | 1999 | 507-510 | |
| Author | Title of Article | |||
| Y. Okamoto | Ianthesines A-D, four novel dibromotyrosine-derived metabolites from a marine sponge, Ianthella sp. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron | 56 | 2000 | 5813-5818 | |
| Author | Title of Article | |||
| Y. Okamoto | Iantherans A and B, unique dimeric polybrominated benzofurans as Na, K-ATPase inhibitors from a marine sponge, Ianthella sp. | |||
| Journal | Volume | Year | Pages Concerned | |
| Bioorg. Med. Chem. | 9 | 2000 | 179-183 | |
| Author | Title of Article | |||
| Y. Okamoto | Aplysiallene, a new bromoallene as a Na, K-ATPase inhibitor from the sea hare Aplysia kurodai. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotechnol. Biochem. | 75 | 2000 | 474-476 | |
| Author | Title of Article | |||
| N. Orihara | Studies of the biosynthesis of terpenoid compounds produced by actinomycetes. 3. Biosynthesis of the isoprenoid side chain of novobiocin via the non-mevalonate pathway in Streptomyces niveus. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Antibiot. | 51 | 1998 | 676-678 | |
| Author | Title of Article | |||
| T. Kuzuyama | Dircct formation of 2-C-methyl-D-erythritol 4-phosphate from 1-deoxy-D-xylulose 5-phosphate by 1-deoxy-D-xylulose 5-phosphate reductoisomerase. a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 39 | 1998 | 4509-4512 | |
| Author | Title of Article | |||
| T. Kuzuyama | Phosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 39 | 1998 | 7913-7916 | |
| Author | Title of Article | |||
| S. Takahashi | Purification, characterization, and cloning of a eubacterial 3-hydroxy-3-methylglutaryl coenzyme A reductase, a key enzyme involved in biosynthesis of terpenoids. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Bacteriol. | 181 | 1999 | 1256-1263 | |
| Author | Title of Article | |||
| T. Kuzuyama | Construction and characterization of Escherichia coli disruptants defective in the yaeM gene. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotechnol. Biochem. | 63 | 1999 | 776-778 | |
| Author | Title of Article | |||
| T. Kuzuyama | Cloning and expression in Escherichia coli of 2-hydroxypropylphosphonic acid epoxidase from the fosfomycin-producing organism, Pseudomonas syringae PB-5123. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotechnol. Biochem. | 63 | 1999 | 2222-2224 | |
| Author | Title of Article | |||
| T. Kuzuyama | Formation of 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol from 2-C-methyl-D-erythritol 4-phosphate by 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase, a new enzyme in the nonmevalonate pathway. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 41 | 2000 | 703-706 | |
| Author | Title of Article | |||
| T. Kuzuyama | Cloning and characterization of 1-deoxy-D-xylulose 5-phosphate synthase from Streptomyces sp. strain CL190, which uses both the mevalonate and nonmevalonate pathways for isopentenyl diphosphate biosynthesis. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Bacteriol. | 182 | 2000 | 891-897 | |
| Author | Title of Article | |||
| T. Kuzuyama | Conversion of 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol to its 2-phospho derivative by 4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol kinase. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 41 | 2000 | 2925-2928 | |
| Author | Title of Article | |||
| M. Takagi | Formation of 2-C-methyl-D-erythritol 2, 4-cyclodiphosphate from 2-phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 41 | 2000 | 3395-3398 | |
| Author | Title of Article | |||
| T. Kuzuyama | Characterization of 1-deoxy-D-xylulose 5-phosphate reductoisomerase, an enzyme involved in the biosynthesis of isopentenyl diphosphate, and identification of its catalytic amino acid residues. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Biol. Chem. | 275 | 2000 | 19928-19932 | |
| Author | Title of Article | |||
| K. Kakinuma | New approach to multiply deuterated isoprenoids using triply engineered Escherichia coli and its potential as a tool for mechanistic enzymology. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 123 | 2001 | 1238-1239 | |
| Author | Title of Article | |||
| Y. Hamano | Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid antibiotic-producing Streptomyces strain. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotechnol. Biochem. | 75 | 2001 | in press | |
| Author | Title of Article | |||
| J. -Q. Liu | L-allo-Threonine aldolase from Aeromonas jandaei DK-39: Gene cloning, nucleotide sequencing, and identification of the pyridoxal 5'-phosphate-binding lysine by site-directed mutagenesis. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Bacteriol. | 179 | 1997 | 3555-3560 | |
| Author | Title of Article | |||
| J. -Q. Liu | he GLYl gene of Saccharomyces cerevisiae encodes a low specific L-threonine aldolase that catalyzes cleavage of L-threonine and L-allo-threonine and L-threonine to glycine: expression of the gene in Escherichia coli and purification and characterization of the enzyme. | |||
| Journal | Volume | Year | Pages Concerned | |
| Eur. J. Biochem. | 245 | 1997 | 289-293 | |
| Author | Title of Article | |||
| T. Dairi | Studies on antibiotic-biosynthetic genes and enzymes catalyzing unique reactions. | |||
| Journal | Volume | Year | Pages Concerned | |
| Actinomycetologica | 12 | 1998 | 75-83 | |
| Author | Title of Article | |||
| J. -Q. Liu | Low-secificity L-threonine aldolase of Pseudomonas sp. NCIMB 10558: purification, characterization and its application to beta-hydroxy-alpha-amino acid synthesis. | |||
| Journal | Volume | Year | Pages Concerned | |
| Appl. Microbiol. Biotechnol. | 49 | 1998 | 702-708 | |
| Author | Title of Article | |||
| J. -Q. Liu | Gene cloning nucleotide sequencing, and purification and characterization of thelow specificity L-threonine aldolase from Pseudomonas sp. strain NCIMB 10558. | |||
| Journal | Volume | Year | Pages Concerned | |
| Appl. Environ. Microbiol. | 64 | 1998 | 549-554 | |
| Author | Title of Article | |||
| J. -Q. Liu | Gene cloning, biochemical characterization and physiological role of a thermostable low-specificity L-threonine aldolase from Escherichia coli. | |||
| Journal | Volume | Year | Pages Concerned | |
| Eur. J. Biochem. | 254 | 1998 | 220-22 | |
| Author | Title of Article | |||
| J. -Q. Liu | A novel metal-activated pyridoxal enzyme with a unique primary structure, low specificity D-threonine aldolase from Arthrobacter sp. stain DK-38. Molecular cloning and cofactor characterization. | |||
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| J. Biol. Chem. | 273 | 1998 | 16678-16685 | |
| Author | Title of Article | |||
| J. -Q. Liu | A new route to L-threo-3-[4-(methylthio)phenylserine], a key intermediate for the synthesis of antibiotics: recombinant low-specificity D-threonine aldolase-catalyzed stereospecific resolution. | |||
| Journal | Volume | Year | Pages Concerned | |
| Appl. Microbiol. Biotechnol. | 51 | 1999 | 586-591 | |
| Author | Title of Article | |||
| T. Dairi | Cloning of the gene encoding 3-hydroxy-3-methylglutaryl coenzyme A reductase from terpenoid antibiotics-producing Stereptomyces strains. | |||
| Journal | Volume | Year | Pages Concerned | |
| Mol. Gen. Genet. | 262 | 2000 | 957-964 | |
| Author | Title of Article | |||
| J. Q. Liu | Gene cloning and overproduction of low-specificity D-threonine aldolase from Alcaligenes xylosaxidans and its application for production of a key intermediate for parkinsonism drug. | |||
| Journal | Volume | Year | Pages Concerned | |
| Appl. Microbiol. Biotechnol. | 54 | 2000 | 44-51 | |
| Author | Title of Article | |||
| Y. Hamano | Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid antibiotic-producing Streptomyces strain. | |||
| Journal | Volume | Year | Pages Concerned | |
| Biosci. Biotech. Biochem. | 75 | 2001 | in press | |
| Author | Title of Article | |||
| S. Sakuda | Mechanism of the cyclopentane ring formation of allosamizoline, an aminocyclitol derivative of the chitinase inhibitor allosamidin. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 37 | 1996 | 5711-5714 | |
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| K. -D. Spindler | Effect of demethylation on the chitinase inhibitory activity of allosamidin. | |||
| Journal | Volume | Year | Pages Concerned | |
| Arch. Insect Biochem. Physiol. | 26 | 1997 | 223-227 | |
| Author | Title of Article | |||
| S. Sakuda | Preparation of biotinylated allosamidins with strong chitinase inhibitory activities. | |||
| Journal | Volume | Year | Pages Concerned | |
| Bioorganic & Medicinal Chemistry Letters | 8 | 1998 | 2987-2990 | |
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| T. Watanabe | Family 19 chitinases of Streptomyces species : characterization and distribution. | |||
| Journal | Volume | Year | Pages Concerned | |
| Microbiology | 145 | 1999 | 3353-3363 | |
| Author | Title of Article | |||
| S. Sakuda | Biosynthetic studies on the cyclopentane ring formation of allosamizoline, an aminocyclitol component of the chitinase inhibitor, allosamidin. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem | 66 | 2001 | in press | |
| Author | Title of Article | |||
| S. Sakuda | Aflastatin A, a novel inhibitor of aflatoxin production of Aspergillus parasiticus from Streptomyces. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 118 | 1996 | 7855-7856 | |
| Author | Title of Article | |||
| S. Sakuda | A novel linear polyene antibiotics: linearmycins. | |||
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| J. Chem Soc. Perkin. Trans. 1 | 1996 | 2315-2319 | ||
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| M. Ono | Aflastain A, a nivel inhibitor of aflatoxin production by aflatoxigenic fungi. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Antibiot. | 50 | 1997 | 111-118 | |
| Author | Title of Article | |||
| S. Sakuda | Structure of blasticidin A. | |||
| Journal | Volume | Year | Pages Concerned | |
| Tetrahedron Lett. | 38 | 1997 | 7399-7402 | |
| Author | Title of Article | |||
| M. Ono | Structues and biosynthesis of aflastatins: novel inhibitors of aflatoxin production by Aspergillus parasiticus. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Antibiot. | 51 | 1998 | 1019-1028 | |
| Author | Title of Article | |||
| H. Ikeda | Absolute configuration of aflastatin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Org. Chem. | 65 | 2000 | 438-444 | |
| Author | Title of Article | |||
| S. Sakuda | Blasticidin A as an Inhibitor of aflatoxin production by Aspergillus parasiticus. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Antibiot. | 53 | 2000 | 1265-1271 | |
| Author | Title of Article | |||
| S. Sakuda | Blasticidin A derivatives with highly specific Inhibitory activity toward aflatoxin production In Aspergillus parasiticus. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Antibiot. | 53 | 2000 | 1378-1384 | |
| Author | Title of Article | |||
| M. Murata | Labeling pattern of okadaic acid from 18O2 and [18O2]acetate elucidated by collision-induced dissociation tandem mass spectrometry. | |||
| Journal | Volume | Year | Pages Concerned | |
| J. Am. Chem. Soc. | 120 | 1998 | 147-151 | |
| Author | Title of Book | ||
| S. Sakuda | Biologically Active Natural Products: Agrochemicals | ||
| Publisher | Year | Pages | |
| CRC Press | 1999 | 185-199 | |
| Author | Title of Book | ||
| S. Sakuda | Comprehensive Natural Products Chemistry | ||
| Publisher | Year | Pages | |
| Pergamon | 1999 | 139-158 | |
| Author | Title of Book | ||
| K. Shin-ya | Real-time analysis of biomolecular interactions | ||
| Publisher | Year | Pages | |
| Springer-Verlag | 2000 | 180-186 | |