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Masayuki Satake
Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

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Journal article
Published: 22 January 2021 in Toxins
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Two different types of polycyclic ether toxins, namely brevisulcenals (KBTs) and brevisulcatic acids (BSXs), produced by the red tide dinoflagellate Karenia brevisulcata, were the cause of a toxic incident that occurred in New Zealand in 1998. Four major components, KBT-F, -G, -H, and -I, shown to be cytotoxic and lethal in mice, were isolated from cultured K. brevisulcata cells, and their structures were elucidated by spectroscopic analyses. New analogues, brevisulcenal-A1 (KBT-A1) and brevisulcenal-A2 (KBT-A2), toxins of higher polarity than that of known KBTs, were isolated from neutral lipophilic extracts of bulk dinoflagellate culture extracts. The structures of KBT-A1 and KBT-A2 were elucidated as sulfated analogues of KBT-F and KBT-G, respectively, by NMR and matrix-assisted laser desorption/ionization tandem mass spectrometry (MALDI TOF/TOF), and by comparison with the spectra of KBT-F and KBT-G. The cytotoxicities of the sulfate analogues were lower than those of KBT-F and KBT-G.

ACS Style

Masayuki Satake; Raku Irie; Patrick Holland; D Harwood; Feng Shi; Yoshiyuki Itoh; Fumiaki Hayashi; Huiping Zhang. Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata. Toxins 2021, 13, 82 .

AMA Style

Masayuki Satake, Raku Irie, Patrick Holland, D Harwood, Feng Shi, Yoshiyuki Itoh, Fumiaki Hayashi, Huiping Zhang. Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata. Toxins. 2021; 13 (2):82.

Chicago/Turabian Style

Masayuki Satake; Raku Irie; Patrick Holland; D Harwood; Feng Shi; Yoshiyuki Itoh; Fumiaki Hayashi; Huiping Zhang. 2021. "Brevisulcenals-A1 and A2, Sulfate Esters of Brevisulcenals, Isolated from the Red Tide Dinoflagellate Karenia brevisulcata." Toxins 13, no. 2: 82.

Special issue article
Published: 03 February 2020 in Chirality
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Marine dinoflagellates produce a unique family of bioactive substances featuring multiple ether rings aligned in a ladder shape. These are large, complex molecules with potent bioactivity. Targeted chiral centers sit on either the skeletal ladders or on the side chains of these compounds. However, the laborious steps of isolation and purification severely diminish the amount of sample available for assigning these chiral centers via structural investigations. Three important methods were used to assign the stereochemistry of the molecules, (a) circular dichroism (CD) spectroscopy, (b) labeling with fluorescent chiral reagents for high‐performance liquid chromatography (HPLC) analysis, and (c) derivatization with anisotropic reagents for nuclear magnetic resonance (NMR) analysis. The addition of fluorescent chiral reagents allowed for the use of much less material than typically required. In this review, we present examples of the determination of absolute configurations in ladder‐shaped polyethers. The targeted compounds include ciguatoxins (CTXs), gymnocin‐B, gambieric acids, prymnesin‐2, maitotoxin, yessotoxins, gambierol, brevisamide, and brevisin.

ACS Style

Masayuki Satake; Takeshi Yasumoto. Methods for determining the absolute configurations of marine ladder‐shaped polyethers. Chirality 2020, 32, 474 -483.

AMA Style

Masayuki Satake, Takeshi Yasumoto. Methods for determining the absolute configurations of marine ladder‐shaped polyethers. Chirality. 2020; 32 (4):474-483.

Chicago/Turabian Style

Masayuki Satake; Takeshi Yasumoto. 2020. "Methods for determining the absolute configurations of marine ladder‐shaped polyethers." Chirality 32, no. 4: 474-483.

Communication
Published: 22 January 2020 in Molecules
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A new aplysiatoxin derivative, neo-aplysiatoxin A (1), along with seven known compounds, neo-debromoaplysiatoxin A (2), dolastatin 3 (3), lyngbic acid (4), malyngamide M (5), hermitamide A (6), (−)-loliolide (7), and (+)-epiloliolide (8), was isolated from the Okinawan cyanobacterium Moorea producens. Their structures were elucidated on the basis of spectroscopic data, including high-resolution mass spectrometry and nuclear magnetic resonance. The compounds were evaluated for cytotoxic and diatom growth inhibition activities.

ACS Style

Mioko Kawaguchi; Masayuki Satake; Bo-Tao Zhang; Yue-Yun Xiao; Masayuki Fukuoka; Hajime Uchida; Hiroshi Nagai. Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens. Molecules 2020, 25, 457 .

AMA Style

Mioko Kawaguchi, Masayuki Satake, Bo-Tao Zhang, Yue-Yun Xiao, Masayuki Fukuoka, Hajime Uchida, Hiroshi Nagai. Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens. Molecules. 2020; 25 (3):457.

Chicago/Turabian Style

Mioko Kawaguchi; Masayuki Satake; Bo-Tao Zhang; Yue-Yun Xiao; Masayuki Fukuoka; Hajime Uchida; Hiroshi Nagai. 2020. "Neo-Aplysiatoxin A Isolated from Okinawan Cyanobacterium Moorea Producens." Molecules 25, no. 3: 457.

Communication
Published: 21 June 2019 in Toxins
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Cyanobacteria have been shown to produce a number of bioactive compounds, including toxins. Some bioactive compounds obtained from a marine cyanobacterium Moorea producens (formerly Lyngbya majuscula) have been recognized as drug leads; one of these compounds is aplysiatoxin. We have isolated various aplysiatoxin derivatives from a M. producens sample obtained from the Okinawan coastal area. The frozen sample was extracted with organic solvents. The ethyl acetate layer was obtained from the crude extracts via liquid-liquid partitioning, then separated by HPLC using a reversed-phase column. Finally, 1.1 mg of the compound was isolated. The chemical structure of the isolated compound was elucidated with spectroscopic methods, using HR-MS and 1D and 2D NMR techniques, and was revealed to be oscillatoxin I, a new member of the aplysiatoxin family. Oscillatoxin I showed cytotoxicity against the L1210 mouse lymphoma cell line and diatom growth-inhibition activity against the marine diatom Nitzschia amabilis.

ACS Style

Hiroshi Nagai; Shingo Sato; Kaori Iida; Kazutaka Hayashi; Mioko Kawaguchi; Hajime Uchida; Masayuki Satake. Oscillatoxin I: A New Aplysiatoxin Derivative, from a Marine Cyanobacterium. Toxins 2019, 11, 366 .

AMA Style

Hiroshi Nagai, Shingo Sato, Kaori Iida, Kazutaka Hayashi, Mioko Kawaguchi, Hajime Uchida, Masayuki Satake. Oscillatoxin I: A New Aplysiatoxin Derivative, from a Marine Cyanobacterium. Toxins. 2019; 11 (6):366.

Chicago/Turabian Style

Hiroshi Nagai; Shingo Sato; Kaori Iida; Kazutaka Hayashi; Mioko Kawaguchi; Hajime Uchida; Masayuki Satake. 2019. "Oscillatoxin I: A New Aplysiatoxin Derivative, from a Marine Cyanobacterium." Toxins 11, no. 6: 366.

Short communication
Published: 10 April 2019 in Tetrahedron Letters
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Alexandrolide (1), an allelopathic diatom growth inhibitor, was isolated from the cell free culture media of the dinoflagellate Alexandrium catenella, which is known as a paralytic shellfish toxin producer. The structure of 1 including partial absolute configuration was elucidated by detailed analyses of NMR spectra, protection of 1,3-diols with acetonide, and a modified Mosher method. The structure of 1 is characterized by a 19-membered ring structure comprising a dehydroalanine and a docosanoic acid derivative possessing a ketone, four hydroxy groups, an ester, and three branching methyls in the molecule. Alexandrolide showed selective growth inhibition against a diatom but not against dinoflagellates.

ACS Style

Masayuki Satake; Daiki Honma; Ryuichi Watanabe; Yasukatu Oshima. Alexandrolide, a diatom growth inhibitor isolated from the dinoflagellate Alexandrium catenella. Tetrahedron Letters 2019, 60, 1341 -1344.

AMA Style

Masayuki Satake, Daiki Honma, Ryuichi Watanabe, Yasukatu Oshima. Alexandrolide, a diatom growth inhibitor isolated from the dinoflagellate Alexandrium catenella. Tetrahedron Letters. 2019; 60 (19):1341-1344.

Chicago/Turabian Style

Masayuki Satake; Daiki Honma; Ryuichi Watanabe; Yasukatu Oshima. 2019. "Alexandrolide, a diatom growth inhibitor isolated from the dinoflagellate Alexandrium catenella." Tetrahedron Letters 60, no. 19: 1341-1344.

Review article
Published: 09 November 2017 in Journal of Natural Products
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Amphidinols are polyketide metabolites produced by marine dinoflagellates and are chiefly composed of a long linear chain with polyol groups and polyolefins. Two new homologues, amphidinols 20 (AM20, 1) and 21 (AM21, 2), were isolated from Amphidinium carterae collected in Korea. Their structures were elucidated by detailed NMR analyses as amphidinol 6-type compounds with remarkably long polyol chains. Amphidinol 21 (2) has the longest linear structure among the amphidinol homologues reported so far. The congeners, particularly amphidinol 21 (2), showed weaker activity in hemolysis and antifungal assays compared to known amphidinols.

ACS Style

Masayuki Satake; Kimberly Cornelio; Shinya Hanashima; Raymond Malabed; Michio Murata; Nobuaki Matsumori; Huiping Zhang; Fumiaki Hayashi; Shoko Mori; Jong Souk Kim; Chang-Hoon Kim; Jong-Soo Lee. Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure–Activity Relationships. Journal of Natural Products 2017, 80, 2883 -2888.

AMA Style

Masayuki Satake, Kimberly Cornelio, Shinya Hanashima, Raymond Malabed, Michio Murata, Nobuaki Matsumori, Huiping Zhang, Fumiaki Hayashi, Shoko Mori, Jong Souk Kim, Chang-Hoon Kim, Jong-Soo Lee. Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure–Activity Relationships. Journal of Natural Products. 2017; 80 (11):2883-2888.

Chicago/Turabian Style

Masayuki Satake; Kimberly Cornelio; Shinya Hanashima; Raymond Malabed; Michio Murata; Nobuaki Matsumori; Huiping Zhang; Fumiaki Hayashi; Shoko Mori; Jong Souk Kim; Chang-Hoon Kim; Jong-Soo Lee. 2017. "Structures of the Largest Amphidinol Homologues from the Dinoflagellate Amphidinium carterae and Structure–Activity Relationships." Journal of Natural Products 80, no. 11: 2883-2888.

Journal article
Published: 01 January 2016 in HETEROCYCLES
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ACS Style

Masayuki Satake; Raku Irie; Rina Suzuki; Kazuo Tachibana; Patrick T. Holland; D. Tim Harwood; Feng Shi; Paul McNabb; Veronica Beuzenberg; Fumiaki Hayashi; Huiping Zhang. Brevisulcatic Acids from a Marine Microalgal Species Implicated in a Toxic Event in New Zealand. HETEROCYCLES 2016, 92, 45 .

AMA Style

Masayuki Satake, Raku Irie, Rina Suzuki, Kazuo Tachibana, Patrick T. Holland, D. Tim Harwood, Feng Shi, Paul McNabb, Veronica Beuzenberg, Fumiaki Hayashi, Huiping Zhang. Brevisulcatic Acids from a Marine Microalgal Species Implicated in a Toxic Event in New Zealand. HETEROCYCLES. 2016; 92 (1):45.

Chicago/Turabian Style

Masayuki Satake; Raku Irie; Rina Suzuki; Kazuo Tachibana; Patrick T. Holland; D. Tim Harwood; Feng Shi; Paul McNabb; Veronica Beuzenberg; Fumiaki Hayashi; Huiping Zhang. 2016. "Brevisulcatic Acids from a Marine Microalgal Species Implicated in a Toxic Event in New Zealand." HETEROCYCLES 92, no. 1: 45.

Journal article
Published: 09 May 2014 in Bioorganic & Medicinal Chemistry
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Ladder-shaped polycyclic ethers (LSPs) are predicted to interact with membrane proteins; however, the underlying mechanism has not been satisfactorily elucidated. It has been hypothesized that LSPs possess non-specific affinity to α-helical segments of transmembrane proteins. To verify this hypothesis, we constructed a model LSP interaction system in a lipid bilayer. We prepared 5 types of α-helical peptides and reconstituted them in liposomes. The reconstitution and orientation of these peptides in the liposomes were examined using polarized attenuated total reflection infrared (ATR-IR) spectroscopy and gel filtration. The results revealed that 4 peptides were retained in liposomes, and 3 of them formed stable transmembrane structures. The interaction between the LSP and the peptides was investigated using Förster resonance energy transfer (FRET). In the lipid bilayer, the LSP strongly recognized the peptides that possessed aligned hydrogen donating groups with leucine caps. We propose that this leucine-capped 16-amino acid sequence is a potential LPS binding motif.

ACS Style

Kazuya Yamada; Haruki Kuriyama; Toshiaki Hara; Michio Murata; Raku Irie; Yanit Harntaweesup; Masayuki Satake; Seketsu Fukuzawa; Kazuo Tachibana. Interaction analysis of a ladder-shaped polycyclic ether and model transmembrane peptides in lipid bilayers by using Förster resonance energy transfer and polarized attenuated total reflection infrared spectroscopy. Bioorganic & Medicinal Chemistry 2014, 22, 3773 -3780.

AMA Style

Kazuya Yamada, Haruki Kuriyama, Toshiaki Hara, Michio Murata, Raku Irie, Yanit Harntaweesup, Masayuki Satake, Seketsu Fukuzawa, Kazuo Tachibana. Interaction analysis of a ladder-shaped polycyclic ether and model transmembrane peptides in lipid bilayers by using Förster resonance energy transfer and polarized attenuated total reflection infrared spectroscopy. Bioorganic & Medicinal Chemistry. 2014; 22 (14):3773-3780.

Chicago/Turabian Style

Kazuya Yamada; Haruki Kuriyama; Toshiaki Hara; Michio Murata; Raku Irie; Yanit Harntaweesup; Masayuki Satake; Seketsu Fukuzawa; Kazuo Tachibana. 2014. "Interaction analysis of a ladder-shaped polycyclic ether and model transmembrane peptides in lipid bilayers by using Förster resonance energy transfer and polarized attenuated total reflection infrared spectroscopy." Bioorganic & Medicinal Chemistry 22, no. 14: 3773-3780.

Journal article
Published: 01 January 2014 in HETEROCYCLES
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ACS Style

Masayuki Satake; Tomohiro Shirai; Yuki Takimoto; Takefumi Kuranaga; Kazuo Tachibana; Daniel G. Baden; Jeffrey L. C. Wright. Synthesis and Cyclization of a Proposed Biosynthetic Epoxy Intermediate of a Marine Monocyclic Ether Amide, Brevisamide. HETEROCYCLES 2014, 89, 127 .

AMA Style

Masayuki Satake, Tomohiro Shirai, Yuki Takimoto, Takefumi Kuranaga, Kazuo Tachibana, Daniel G. Baden, Jeffrey L. C. Wright. Synthesis and Cyclization of a Proposed Biosynthetic Epoxy Intermediate of a Marine Monocyclic Ether Amide, Brevisamide. HETEROCYCLES. 2014; 89 (1):127.

Chicago/Turabian Style

Masayuki Satake; Tomohiro Shirai; Yuki Takimoto; Takefumi Kuranaga; Kazuo Tachibana; Daniel G. Baden; Jeffrey L. C. Wright. 2014. "Synthesis and Cyclization of a Proposed Biosynthetic Epoxy Intermediate of a Marine Monocyclic Ether Amide, Brevisamide." HETEROCYCLES 89, no. 1: 127.

Review article
Published: 10 May 2012 in The Journal of Organic Chemistry
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Yessotoxin is a ladder-frame polyether produced by the dinoflagellate Protoceratium reticulatum. Previous labeling experiments using 13C-acetate established the unique assembly of the carbon chain from intact and cleaved acetate units. The origins of ether and hydroxy oxygens in the molecule, which would yield further information regarding the assembly of the ladder-frame structure, have yet to be established. In this study, we describe the incorporation of 18O in one experiment where the dinoflagellate was cultured under 18O2 atmosphere and in a second where the culture media was supplemented with [18O2]acetate. Labeled yessotoxin obtained from these experiments was subjected to collision-induced dissociation tandem mass spectrometry to determine the positions of 18O-incorporation pattern in the molecule. Detailed analyses of product ions from the fragmentation processes led to the identification of 18O-labeled positions and the incorporation ratios. The data revealed that the ether oxygens were labeled from 18O2 and the hydroxy oxygen on C32 was derived from [18O2]acetate. These results support a proposed biosynthetic mechanism of marine ladder-frame polyethers that a polyene precursor was oxidized by a monooxygenase after acetate condensation.

ACS Style

Masatoshi Yamazaki; Miho Izumikawa; Kazuo Tachibana; Masayuki Satake; Yoshiyuki Itoh; Masahiro Hashimoto. Origins of Oxygen Atoms in a Marine Ladder-Frame Polyether: Evidence of Monooxygenation by 18O-Labeling and Using Tandem Mass Spectrometry. The Journal of Organic Chemistry 2012, 77, 4902 -4906.

AMA Style

Masatoshi Yamazaki, Miho Izumikawa, Kazuo Tachibana, Masayuki Satake, Yoshiyuki Itoh, Masahiro Hashimoto. Origins of Oxygen Atoms in a Marine Ladder-Frame Polyether: Evidence of Monooxygenation by 18O-Labeling and Using Tandem Mass Spectrometry. The Journal of Organic Chemistry. 2012; 77 (11):4902-4906.

Chicago/Turabian Style

Masatoshi Yamazaki; Miho Izumikawa; Kazuo Tachibana; Masayuki Satake; Yoshiyuki Itoh; Masahiro Hashimoto. 2012. "Origins of Oxygen Atoms in a Marine Ladder-Frame Polyether: Evidence of Monooxygenation by 18O-Labeling and Using Tandem Mass Spectrometry." The Journal of Organic Chemistry 77, no. 11: 4902-4906.

Journal article
Published: 30 March 2012 in Fisheries and aquatic sciences
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ACS Style

Jong-Soo Lee; Masayuki Satake; Yoichi Horigome; Yasukatsu Oshima; Takeshi Yasumoto. Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas. Fisheries and aquatic sciences 2012, 15, 15 -19.

AMA Style

Jong-Soo Lee, Masayuki Satake, Yoichi Horigome, Yasukatsu Oshima, Takeshi Yasumoto. Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas. Fisheries and aquatic sciences. 2012; 15 (1):15-19.

Chicago/Turabian Style

Jong-Soo Lee; Masayuki Satake; Yoichi Horigome; Yasukatsu Oshima; Takeshi Yasumoto. 2012. "Gamakamide-E, a Strongly Bitter Tasting Cyclic Peptide with a Hydantoin Structure from Cultured Oysters Crassostrea gigas." Fisheries and aquatic sciences 15, no. 1: 15-19.

Journal article
Published: 29 February 2012 in Journal of the American Chemical Society
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A novel marine toxin, brevisulcenal-F (KBT-F, from karenia brevisulcata toxin) was isolated from the dinoflagellate Karenia brevisulcata. A red tide of K. brevisulcata in Wellington Harbour, New Zealand, in 1998 was extremely toxic to fish and marine invertebrates and also caused respiratory distress in harbor bystanders. An extract of K. brevisulcata showed potent mouse lethality and cytotoxicity, and laboratory cultures of K. brevisulcata produced a range of novel lipid-soluble toxins. A lipid soluble toxin, KBT-F, was isolated from bulk cultures by using various column chromatographies. Chemical investigations showed that KBT-F has the molecular formula C(107)H(160)O(38) and a complex polycyclic ether nature. NMR and MS/MS analyses revealed the complete structure for KBT-F, which is characterized by a ladder-frame polyether scaffold, a 2-methylbut-2-enal terminus, and an unusual substituted dihydrofuran at the other terminus. The main section of the molecule has 17 contiguous 6- and 7-membered ether rings. The LD(50) (mouse i.p.) for KBT-F was 0.032 mg/kg.

ACS Style

Yuka Hamamoto; Kazuo Tachibana; Patrick T. Holland; Feng Shi; Veronica Beuzenberg; Yoshiyuki Itoh; Masayuki Satake. Brevisulcenal-F: A Polycyclic Ether Toxin Associated with Massive Fish-kills in New Zealand. Journal of the American Chemical Society 2012, 134, 4963 -4968.

AMA Style

Yuka Hamamoto, Kazuo Tachibana, Patrick T. Holland, Feng Shi, Veronica Beuzenberg, Yoshiyuki Itoh, Masayuki Satake. Brevisulcenal-F: A Polycyclic Ether Toxin Associated with Massive Fish-kills in New Zealand. Journal of the American Chemical Society. 2012; 134 (10):4963-4968.

Chicago/Turabian Style

Yuka Hamamoto; Kazuo Tachibana; Patrick T. Holland; Feng Shi; Veronica Beuzenberg; Yoshiyuki Itoh; Masayuki Satake. 2012. "Brevisulcenal-F: A Polycyclic Ether Toxin Associated with Massive Fish-kills in New Zealand." Journal of the American Chemical Society 134, no. 10: 4963-4968.

Journal article
Published: 21 April 2011 in ChemInform
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The first total synthesis of (I) succeeds in 29 steps from commercially available deoxy‐D‐ribose.

ACS Style

Takefumi Kuranaga; Naohito Ohtani; Ryosuke Tsutsumi; Daniel G. Baden; Jeffrey L. C. Wright; Masayuki Satake; Kazuo Tachibana. ChemInform Abstract: Total Synthesis of (-)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether. ChemInform 2011, 42, 1 .

AMA Style

Takefumi Kuranaga, Naohito Ohtani, Ryosuke Tsutsumi, Daniel G. Baden, Jeffrey L. C. Wright, Masayuki Satake, Kazuo Tachibana. ChemInform Abstract: Total Synthesis of (-)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether. ChemInform. 2011; 42 (20):1.

Chicago/Turabian Style

Takefumi Kuranaga; Naohito Ohtani; Ryosuke Tsutsumi; Daniel G. Baden; Jeffrey L. C. Wright; Masayuki Satake; Kazuo Tachibana. 2011. "ChemInform Abstract: Total Synthesis of (-)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether." ChemInform 42, no. 20: 1.

Research article
Published: 22 March 2011 in The Journal of Organic Chemistry
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A polyoxy linear carbon chain compound, prorocentrol (1), was isolated from cultured cells of the dinoflagellate Prorocentrum hoffmannianum, which produces a polyether carboxylic acid, okadaic acid. The structure of 1 was elucidated by detailed analyses of 2D NMR spectra. Compound 1 possesses 30 hydroxy groups, 1 ketone, and 8 double bonds on the C65-linear carbon chain. Its partial relative configuration was deduced by the proton−proton and long-range carbon−proton coupling constants, and compound 1 showed moderate cytotoxicity and antidiatom activity.

ACS Style

Kohtaro Sugahara; Yoshiaki Kitamura; Michio Murata; Masayuki Satake; Kazuo Tachibana. Prorocentrol, a Polyoxy Linear Carbon Chain Compound Isolated from the Toxic Dinoflagellate Prorocentrum hoffmannianum. The Journal of Organic Chemistry 2011, 76, 3131 -3138.

AMA Style

Kohtaro Sugahara, Yoshiaki Kitamura, Michio Murata, Masayuki Satake, Kazuo Tachibana. Prorocentrol, a Polyoxy Linear Carbon Chain Compound Isolated from the Toxic Dinoflagellate Prorocentrum hoffmannianum. The Journal of Organic Chemistry. 2011; 76 (9):3131-3138.

Chicago/Turabian Style

Kohtaro Sugahara; Yoshiaki Kitamura; Michio Murata; Masayuki Satake; Kazuo Tachibana. 2011. "Prorocentrol, a Polyoxy Linear Carbon Chain Compound Isolated from the Toxic Dinoflagellate Prorocentrum hoffmannianum." The Journal of Organic Chemistry 76, no. 9: 3131-3138.

Journal article
Published: 10 February 2011 in ChemInform
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ACS Style

Takefumi Kuranaga; Shuji Ishihara; Naohito Ohtani; Masayuki Satake; Kazuo Tachibana. ChemInform Abstract: Chemoselective Deprotection of Silyl Ethers by DIBALH. ChemInform 2011, 42, 1 .

AMA Style

Takefumi Kuranaga, Shuji Ishihara, Naohito Ohtani, Masayuki Satake, Kazuo Tachibana. ChemInform Abstract: Chemoselective Deprotection of Silyl Ethers by DIBALH. ChemInform. 2011; 42 (10):1.

Chicago/Turabian Style

Takefumi Kuranaga; Shuji Ishihara; Naohito Ohtani; Masayuki Satake; Kazuo Tachibana. 2011. "ChemInform Abstract: Chemoselective Deprotection of Silyl Ethers by DIBALH." ChemInform 42, no. 10: 1.

Rapid communication
Published: 19 January 2011 in Organic Letters
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The first and highly efficient total synthesis of (−)-brevisin has been achieved. The title compound was synthesized in only 29 steps (longest linear sequence) from commercially available starting materials. The synthesis provided over 70 mg of a marine polycyclic ether compound.

ACS Style

Takefumi Kuranaga; Naohito Ohtani; Ryosuke Tsutsumi; Daniel G. Baden; Jeffrey L. C. Wright; Masayuki Satake; Kazuo Tachibana. Total Synthesis of (−)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether. Organic Letters 2011, 13, 696 -699.

AMA Style

Takefumi Kuranaga, Naohito Ohtani, Ryosuke Tsutsumi, Daniel G. Baden, Jeffrey L. C. Wright, Masayuki Satake, Kazuo Tachibana. Total Synthesis of (−)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether. Organic Letters. 2011; 13 (4):696-699.

Chicago/Turabian Style

Takefumi Kuranaga; Naohito Ohtani; Ryosuke Tsutsumi; Daniel G. Baden; Jeffrey L. C. Wright; Masayuki Satake; Kazuo Tachibana. 2011. "Total Synthesis of (−)-Brevisin: A Concise Synthesis of a New Marine Polycyclic Ether." Organic Letters 13, no. 4: 696-699.

Journal article
Published: 10 December 2010 in Tetrahedron
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Biosynthesis of a marine ladder-frame polyether yessotoxin (YTX) produced by the dinofalgellate Protoceratium reticulatum was investigated. The 13C-labeling experiments indicated that the carbons in YTX were derived from acetates, a methyl of methionine and glycolate, and six-membered ring tetrads (rings A–D and H–K) were constructed from repetition of C3 units (m–m–c), which consisted of a methyl of acetate and acetate.

ACS Style

Masatoshi Yamazaki; Kazuo Tachibana; Masayuki Satake. Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether. Tetrahedron 2010, 67, 877 -880.

AMA Style

Masatoshi Yamazaki, Kazuo Tachibana, Masayuki Satake. Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether. Tetrahedron. 2010; 67 (5):877-880.

Chicago/Turabian Style

Masatoshi Yamazaki; Kazuo Tachibana; Masayuki Satake. 2010. "Complete 13C-labeling pattern of yessotoxin a marine ladder-frame polyether." Tetrahedron 67, no. 5: 877-880.

Short communication
Published: 01 December 2010 in Tetrahedron Letters
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ACS Style

Takefumi Kuranaga; Shuji Ishihara; Naohito Ohtani; Masayuki Satake; Kazuo Tachibana. Chemoselective deprotection of silyl ethers by DIBALH. Tetrahedron Letters 2010, 51, 6345 -6348.

AMA Style

Takefumi Kuranaga, Shuji Ishihara, Naohito Ohtani, Masayuki Satake, Kazuo Tachibana. Chemoselective deprotection of silyl ethers by DIBALH. Tetrahedron Letters. 2010; 51 (48):6345-6348.

Chicago/Turabian Style

Takefumi Kuranaga; Shuji Ishihara; Naohito Ohtani; Masayuki Satake; Kazuo Tachibana. 2010. "Chemoselective deprotection of silyl ethers by DIBALH." Tetrahedron Letters 51, no. 48: 6345-6348.

Short communication
Published: 01 September 2010 in Tetrahedron Letters
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Synthesis of the BC/DE ring model of brevisin, a polycyclic ether isolated from the red tide dinoflagellate Karenia brevis, is reported. Comparison of the NMR data of the BC/DE ring model with those corresponding to the same region of brevisin led to the confirmation of its structure around the acyclic juncture.

ACS Style

Takefumi Kuranaga; Masayuki Satake; Daniel G. Baden; Jeffrey L.C. Wright; Kazuo Tachibana. Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction. Tetrahedron Letters 2010, 51, 4673 -4676.

AMA Style

Takefumi Kuranaga, Masayuki Satake, Daniel G. Baden, Jeffrey L.C. Wright, Kazuo Tachibana. Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction. Tetrahedron Letters. 2010; 51 (35):4673-4676.

Chicago/Turabian Style

Takefumi Kuranaga; Masayuki Satake; Daniel G. Baden; Jeffrey L.C. Wright; Kazuo Tachibana. 2010. "Synthesis of the BC/DE ring model of brevisin for confirmation of the structure around the acyclic junction." Tetrahedron Letters 51, no. 35: 4673-4676.

Journal article
Published: 03 July 2010 in Tetrahedron
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An improved synthesis of (−)-brevisamide a marine cyclic ether isolated from the red-tide dinoflagellate Karenia brevis was achieved. The ether ring portion was constructed from an unsaturated lactone, which was prepared enantioselectively via an Evans aldol reaction and one-pot lactonization in the presence of excessive base after an Ando reaction. The ether ring and a dienol side chain fragment were connected via Suzuki–Miyaura coupling.

ACS Style

Ryosuke Tsutsumi; Takefumi Kuranaga; Jeffrey L.C. Wright; Daniel G. Baden; Emiko Ito; Masayuki Satake; Kazuo Tachibana. An improved synthesis of (−)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin. Tetrahedron 2010, 66, 6775 -6782.

AMA Style

Ryosuke Tsutsumi, Takefumi Kuranaga, Jeffrey L.C. Wright, Daniel G. Baden, Emiko Ito, Masayuki Satake, Kazuo Tachibana. An improved synthesis of (−)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin. Tetrahedron. 2010; 66 (34):6775-6782.

Chicago/Turabian Style

Ryosuke Tsutsumi; Takefumi Kuranaga; Jeffrey L.C. Wright; Daniel G. Baden; Emiko Ito; Masayuki Satake; Kazuo Tachibana. 2010. "An improved synthesis of (−)-brevisamide, a marine monocyclic ether amide of dinoflagellate origin." Tetrahedron 66, no. 34: 6775-6782.