Literature DB >> 11388846

Isolation, structure determination, and synthesis of neodysiherbaine A, a new excitatory amino acid from a marine sponge.

R Sakai1, T Koike, M Sasaki, K Shimamoto, C Oiwa, A Yano, K Suzuki, K Tachibana, H Kamiya.   

Abstract

[structure: see text] A new excitatory amino acid, neodysiherbaine A (2), was isolated as a minor constituent of the aqueous extract from the marine sponge Dysidea herbacea. The structure was deduced by spectroscopic methods and established unambiguously by the total synthesis. The present synthesis, including as a key step cross-coupling of the 6/5-bicyclic core with an amino acid residue, is useful in constructing its structural analogues.

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Year:  2001        PMID: 11388846     DOI: 10.1021/ol015798l

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  15 in total

Review 1.  Glutamate receptor ion channels: structure, regulation, and function.

Authors:  Stephen F Traynelis; Lonnie P Wollmuth; Chris J McBain; Frank S Menniti; Katie M Vance; Kevin K Ogden; Kasper B Hansen; Hongjie Yuan; Scott J Myers; Ray Dingledine
Journal:  Pharmacol Rev       Date:  2010-09       Impact factor: 25.468

Review 2.  Marine pharmacology in 2001--2002: marine compounds with anthelmintic, antibacterial, anticoagulant, antidiabetic, antifungal, anti-inflammatory, antimalarial, antiplatelet, antiprotozoal, antituberculosis, and antiviral activities; affecting the cardiovascular, immune and nervous systems and other miscellaneous mechanisms of action.

Authors:  Alejandro M S Mayer; Mark T Hamann
Journal:  Comp Biochem Physiol C Toxicol Pharmacol       Date:  2005 Mar-Apr       Impact factor: 3.228

3.  Improved synthesis and in vitro/in vivo activities of natural product-inspired, artificial glutamate analogs.

Authors:  Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal:  Bioorg Med Chem       Date:  2010-04-21       Impact factor: 3.641

4.  Enantiospecific synthesis of genetically encodable fluorescent unnatural amino acid L-3-(6-acetylnaphthalen-2-ylamino)-2-aminopropanoic acid.

Authors:  Zheng Xiang; Lei Wang
Journal:  J Org Chem       Date:  2011-07-06       Impact factor: 4.354

5.  Studies on an (S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid (AMPA) receptor antagonist IKM-159: asymmetric synthesis, neuroactivity, and structural characterization.

Authors:  Lina Juknaitė; Yutaro Sugamata; Kazuya Tokiwa; Yuichi Ishikawa; Satoshi Takamizawa; Andrew Eng; Ryuichi Sakai; Darryl S Pickering; Karla Frydenvang; Geoffrey T Swanson; Jette S Kastrup; Masato Oikawa
Journal:  J Med Chem       Date:  2013-03-13       Impact factor: 7.446

6.  Regioselective Domino Metathesis of Unsymmetrical 7-Oxanorbornenes with Electron-Rich Vinyl Acetate toward Biologically Active Glutamate Analogues.

Authors:  Masato Oikawa; Minoru Ikoma; Makoto Sasaki; Martin B Gill; Geoffrey T Swanson; Keiko Shimamoto; Ryuichi Sakai
Journal:  European J Org Chem       Date:  2009-11-01

Review 7.  Recent progress in neuroactive marine natural products.

Authors:  Ryuichi Sakai; Geoffrey T Swanson
Journal:  Nat Prod Rep       Date:  2014-01-17       Impact factor: 13.423

8.  Pharmacological activity of C10-substituted analogs of the high-affinity kainate receptor agonist dysiherbaine.

Authors:  L Leanne Lash-Van Wyhe; Pekka A Postila; Koichi Tsubone; Makoto Sasaki; Olli T Pentikäinen; Ryuichi Sakai; Geoffrey T Swanson
Journal:  Neuropharmacology       Date:  2009-12-04       Impact factor: 5.250

Review 9.  Ligands for ionotropic glutamate receptors.

Authors:  Geoffrey T Swanson; Ryuichi Sakai
Journal:  Prog Mol Subcell Biol       Date:  2009

10.  Novel analogs and stereoisomers of the marine toxin neodysiherbaine with specificity for kainate receptors.

Authors:  L Leanne Lash; James M Sanders; Nobuyuki Akiyama; Muneo Shoji; Pekka Postila; Olli T Pentikäinen; Makoto Sasaki; Ryuichi Sakai; Geoffrey T Swanson
Journal:  J Pharmacol Exp Ther       Date:  2007-11-21       Impact factor: 4.030

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