Results 71 to 80 of about 175 (106)

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 Roush
exaly   +3 more sources

Confirmation of the Absolute Configuration at C45 of Amphidinol 3

Journal of Natural Products, 2012
Amphidinol 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, Makoto, Ebine, Nobuaki, Matsumori, Michio, Murata, Tohru, Oishi   +4 more
openaire   +2 more sources

Isolation, structural determination and synthetic approaches toward amphidinol 3

Natural Product Reports, 2014
This review highlights the isolation and the structural determination of amphidinol 3 (AM3), as well as the synthetic efforts to its preparation. The mechanism of action of AM3 will not be developed herein.
Janine Cossy, Gilles Hanquet
exaly   +3 more sources

Stereoselective Synthesis of the C1–C29 Part of Amphidinol 3

The Journal of Organic Chemistry, 2015
Stereoselective synthesis of the C1-C29 part of amphidinol 3 (AM3) was achieved. The C1-C20 part was assembled from three building blocks via regioselective cross metathesis to form the C4-C5 double bond and addition of an alkenyllithium and a lithium acetylide to two Weinreb amides followed by asymmetric reduction to form the C9-C10 and C14-C15 bonds,
Takeshi, Tsuruda, Makoto, Ebine, Aya, Umeda, Tohru, Oishi   +3 more
openaire   +2 more sources

Effects of lipid constituents on membrane-permeabilizing activity of amphidinols

Bioorganic & Medicinal Chemistry, 2008
Amphidinols (AMs) are a new class of polyhydroxyl polyene compounds with potent antifungal activity. Membrane-permeabilizing activities of AM2, AM3, and AM6 were examined using fluorescent-dye leakage experiments with various phosphatidylcholines (PCs) and sterols. All the AMs tested showed the potent activity to cholesterol-containing liposomes.
Nagy, Morsy, Toshihiro, Houdai, Keiichi, Konoki, Nobuaki, Matsumori, Tohru, Oishi, Michio, Murata   +5 more
openaire   +2 more sources

Diastereoselective synthesis of the C17–C30 fragment of amphidinol 3

Organic & Biomolecular Chemistry, 2012
The 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 ...
Rival, Nicolas, Hazelard, Damien, Hanquet, Gilles, Kreuzer, Thomas, Bensoussan, Charlelie, Reymond, Sébastien, Cossy, Janine, Colobert, Françoise   +7 more
openaire   +2 more sources

Structure of Membrane-Bound Amphidinol 3 in Isotropic Small Bicelles

Organic Letters, 2008
Amphidinol 3 (AM3) exhibits a potent membrane permeabilizing activity by forming pores in biological membranes. We examined the conformation and location of AM3 using isotropic bicelles, a more natural membrane model than micelles. The results show that AM3 takes turn structures at the two tetrahydropyran rings.
Toshihiro, Houdai, Nobuaki, Matsumori, Michio, Murata   +2 more
openaire   +2 more sources

Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3

Organic Letters, 2013
Stereoselective synthesis of the C43-C67 part of amphidinol 3 (AM3) and its C51-epimer was achieved starting from a common intermediate corresponding to the tetrahydropyran moiety of AM3, via asymmetric oxidations and Julia-Kocienski olefination. By comparing NMR data of the synthetic specimens with those of AM3, the absolute configuration at C51 of ...
Makoto, Ebine, Mitsunori, Kanemoto, Yoshiyuki, Manabe, Yosuke, Konno, Ken, Sakai, Nobuaki, Matsumori, Michio, Murata, Tohru, Oishi   +7 more
openaire   +2 more sources

Efficient Syntheses of the Polyene Fragments Present in Amphidinols

Synlett, 2007
The C53-C67 and C53-C65 polyene fragments of amphidinols have been synthesized in an efficient and convergent fashion from sorbic acid in good overall yields (30-31%) by employing a chemoselective cross-metathesis of a Weinreb amide and a Julia-Kocienski olefination as the key steps.
Janine Cossy, Tomoki Tsuchiya, Laurent Ferrié, Sébastien Reymond, Thomas Kreuzer, Françoise Colobert, Pierre Jourdain, István Markó   +7 more
openaire   +1 more source

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, Nobuaki, Matsumori, Masashi, Tsuda, Michio, Murata   +3 more
openaire   +2 more sources