2007
DOI: 10.1021/tx700016m
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Clarification of the C-35 Stereochemistries of Dinophysistoxin-1 and Dinophysistoxin-2 and Its Consequences for Binding to Protein Phosphatase

Abstract: Okadaic acid analogues are well known as protein phosphatase inhibitors and occur naturally in marine shellfish feeding on dinoflagellates of the genus Dinophysis, leading to diarrhetic shellfish poisoning of shellfish consumers. Knowledge of the correct structures for these toxins is important in understanding their toxicology, biochemistry, and biosynthesis. We have performed extensive NMR analyses on okadaic acid (1), dinophysistoxin-1 (DTX-1), and dinophysistoxin-2 (DTX-2) obtained from natural sources. Co… Show more

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Cited by 55 publications
(51 citation statements)
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“…The cells were rinsed on the sieve with fresh f/2 media, and kept wet to minimize breakage. The cells were washed into a 15-mL Falcon tube Tachibana and Scheuer, 1981;(2) Murata et al, 1982;(3) Larsen et al, 2007;(4) Yasumoto et al, 1985;(5) Marr et al, 1992 (6) Hu et al, 1995a;(7) Hu et al, 1995b;(8) Cruz et al, 2006;(9) Fernandez et al, 2003;(10) Suarez-Gomez et al, 2005;(11) Yasumoto et al, 1989;(12) Hu et al, 1992a;(13) Suarez-Gomez et al, 2001;(14) Miles et al, 2006;(15) Torgersen et al, 2008a;(16) Norte et al, 1994. using fresh f/2 media (13 mL), and the tube immersed in a water bath at 100 C for 5 min. The samples were frozen at À20 C, thawed at room temperature, and sonicated in a water bath (Fisher ultrasonic cleaner, Model FS30H) for 15 min before solid-phase extraction (SPE).…”
Section: Sample Preparation and Extraction Of Toxinsmentioning
confidence: 99%
“…The cells were rinsed on the sieve with fresh f/2 media, and kept wet to minimize breakage. The cells were washed into a 15-mL Falcon tube Tachibana and Scheuer, 1981;(2) Murata et al, 1982;(3) Larsen et al, 2007;(4) Yasumoto et al, 1985;(5) Marr et al, 1992 (6) Hu et al, 1995a;(7) Hu et al, 1995b;(8) Cruz et al, 2006;(9) Fernandez et al, 2003;(10) Suarez-Gomez et al, 2005;(11) Yasumoto et al, 1989;(12) Hu et al, 1992a;(13) Suarez-Gomez et al, 2001;(14) Miles et al, 2006;(15) Torgersen et al, 2008a;(16) Norte et al, 1994. using fresh f/2 media (13 mL), and the tube immersed in a water bath at 100 C for 5 min. The samples were frozen at À20 C, thawed at room temperature, and sonicated in a water bath (Fisher ultrasonic cleaner, Model FS30H) for 15 min before solid-phase extraction (SPE).…”
Section: Sample Preparation and Extraction Of Toxinsmentioning
confidence: 99%
“…Estrutura química da ficotoxina diarreica ácido okadaico (OA) e seus principais derivados dinophysistoxina 1 (DTX1), dinophysistoxina 2 (DTX2) e dinophysistoxina 3 (DTX3). Figura adaptada de Larsen et al (2007). Papel das Ficotoxinas Diarreicas na Biota Aquática e Aquicultura preferencialmente em vieiras.…”
Section: Toxinas Diarreicasunclassified
“…The chain length of the acyl moiety can range from C 14 to C 22 and may contain between 0 and 6 unsaturated carbon-carbon bonds. The most predominant fatty acid identified in the acylated derivatives is reported to be hexadecanoic (palmitic, C 16:0 ) acid (cited in Hallegraeff et al, 1995;Wright, 1995;EU/SANCO, 2001 Larsen et al, 2007).…”
Section: Chemical Characteristicsmentioning
confidence: 99%