Results 101 to 110 of about 276 (135)
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Synthesis of the C(43)−C(67) Fragment of Amphidinol 3
Organic Letters, 2005[reaction: see text] A synthesis of the C(43)-C(67) fragment of amphidinol 3 (AM3) has been accomplished by a route that features the use of a double allylboration reaction for synthesis of 1,5-diol 4b, which serves as a precursor to dihydropyran 11.
William R Roush
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Direct and Stereospecific Interaction of Amphidinol 3 with Sterol in Lipid Bilayers
Biochemistry, 2014 Amphidinol 3 (AM3), a polyhydroxy-polyene metabolite from the dinoflagellate Amphidinium klebsii, possesses potent antifungal activity. Although AM3 permeabilizes phospholipid membranes only in the presence of sterol, the detailed molecular basis by which AM3 recognizes sterols in membranes remains unknown.
Rafael Atillo, Espiritu +3 more
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Total Synthesis of Amphidinol 3
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2021Tohru Oishi
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Chemistry - an Asian Journal
Abstract Structure–activity relationship studies of artificial analogues of amphidinol 3 (AM3) were conducted. Based on the truncated molecule corresponding to the C21–C67 section of AM3, which elicited comparable antifungal activity to the parent compound, its stereoisomers were synthesized from polyol, bis‐THP, and polyene units via
Yoko Yasuno +2 more
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Abstract Structure–activity relationship studies of artificial analogues of amphidinol 3 (AM3) were conducted. Based on the truncated molecule corresponding to the C21–C67 section of AM3, which elicited comparable antifungal activity to the parent compound, its stereoisomers were synthesized from polyol, bis‐THP, and polyene units via
Yoko Yasuno +2 more
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Membrane permeabilizing action of amphidinol 3 and theonellamide A in raft-forming lipid mixtures
Zeitschrift für Naturforschung C, 2016 Abstract Amphidinol 3 (AM3) and theonellamide A (TNM-A) are potent antifungal compounds produced by the dinoflagellate Amphidinium klebsii and the sponge Theonella spp., respectively. Both of these metabolites have been demonstrated to interact with membrane lipids ultimately resulting in a compromised bilayer integrity.
Espiritu, R. A.
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Isolation and Structural Elucidation of New Amphidinol Analogues from Amphidinium carterae Cultivated in a Pilot-Scale Photobioreactor [PDF]
Marine Drugs, 2021 The demand for valuable products from dinoflagellate biotechnology has increased remarkably in recent years due to their many prospective applications.
Adrian Morales-Amador +2 more
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Stereoselective Synthesis of the C(53)-C(67) Polyene Fragment of Amphidinol 3
Synlett, 2007 A stereoselective synthesis of the polyene fragment C(53)-C(67) of amphidinol 3 is described using a sequence of reduction, benzoylation, and reductive elimination for the stereospecific preparation of the polyene motif as key steps starting from ...
Françoise Colobert +2 more
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Syntheses of C22–C29 and C20–C29 sections of amphidinol 3
Tetrahedron LettersYoko Yasuno, Tohru Oishi
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Confirmation of the Absolute Configuration at C45 of Amphidinol 3
Journal of Natural Products, 2012Amphidinol 3 (AM3), a membrane-active agent isolated from the dinoflagellate Amphidinium klebsii, consists of a long carbon chain containing 25 stereogenic centers. Although the absolute configuration of AM3 was determined by extensive NMR analysis and degradation of the natural product, the partial structure corresponding to the tetrahydropyran ring ...
Yoshiyuki, Manabe +4 more
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Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3
Organic & Biomolecular Chemistry, 2012The diastereoselective synthesis of the C17-C30 fragment of amphidinol 3 (AM3) 1 was achieved from the enantio-enriched aldehyde 20, Weinreb amide 14 and 2-bromo-3-(trimethylsilyl)propene, which was used as a bifunctional conjunctive reagent. The absolute configuration of the stereogenic centers, in both aldehyde 20 and Weinreb amide 14, were ...
Nicolas, Rival +7 more
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