Isotactic polymethoxy 1-alkenes from blue-green algae. Synthesis and absolute stereochemistry

Mori, Yoshihiro; Kohchi, Yasunori; Suzuki, Makoto; Carmeli, Shmuel; Moore, Richard E.; Patterson, Gregory M. L.

doi:10.1021/jo00002a027

Cited by 55 publications

(48 citation statements)

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“…In fact, PMAs have been previously described from a wide range of cyanobacteria for more than three decades. [17][18][19][20] However, only recently have they been linked to biological activity and specifically observed teratogenicity in the zebrafish embryo model. 14 As such, no data currently exist with respect to possible mechanisms, or biochemical, molecular, or cellular targets, of these compounds.…”

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confidence: 99%

High-Resolution Magic Angle Spinning Nuclear Magnetic Resonance of Intact Zebrafish Embryos Detects Metabolic Changes Following Exposure to Teratogenic Polymethoxyalkenes from Algae

et al. 2016

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Techniques based on nuclear magnetic resonance (NMR) for imaging and chemical analyses of in vivo, or otherwise intact, biological systems are rapidly emerging and finding diverse applications within a wide range of fields. Very recently, several NMR-based techniques have been developed for the zebrafish as a model animal system. In the current study, the novel application of high-resolution magic angle spinning (HR-MAS) NMR is presented as a means of metabolic profiling of intact zebrafish embryos. Toward investigating the utility of HR-MAS NMR as a toxicological tool, these studies specifically examined metabolic changes of embryos exposed to polymethoxy-1-alkenes (PMAs)-a recently identified family of teratogenic compounds from freshwater algae-as emerging environmental contaminants. One-dimensional and two-dimensional HR-MAS NMR analyses were able to effectively identify and quantify diverse metabolites in early-stage (£36 h postfertilization) embryos. Subsequent comparison of the metabolic profiles between PMA-exposed and control embryos identified several statistically significant metabolic changes associated with subacute exposure to the teratogen, including (1) elevated inositol as a recognized component of signaling pathways involved in embryo development; (2) increases in several metabolites, including inositol, phosphoryl choline, fatty acids, and cholesterol, which are associated with lipid composition of cell membranes; (3) concomitant increase in glucose and decrease in lactate; and (4) decreases in several biochemically related metabolites associated with central nervous system development and function, including c-aminobutyric acid, glycine, glutamate, and glutamine. A potentially unifying model/hypothesis of PMA teratogenicity based on the data is presented. These findings, taken together, demonstrate that HR-MAS NMR is a promising tool for metabolic profiling in the zebrafish embryo, including toxicological applications.

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High-Resolution Magic Angle Spinning Nuclear Magnetic Resonance of Intact Zebrafish Embryos Detects Metabolic Changes Following Exposure to Teratogenic Polymethoxyalkenes from Algae

et al. 2016

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“…The alcohol 5 was then TBS-protected and the olefin oxidatively cleaved with potassium osmate and sodium periodate to afford the aldehyde 6. 10 The key ZnCl 2 -mediated, tandem Mukaiyama aldol-lactonisation (TMAL) 3 between the b-hydroxy aldehyde 6 and the thiopyridyl ketene acetal 7 (prepared in four steps from 6-bromohexanoic acid; Scheme S2w) afforded the trans-b-lactone 8 as separable 9 : 1 anti/syn diastereomers in 39% yield after desilylation.…”

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Click-based synthesis and proteomic profiling of lipstatin analogues

Ngai

Yang

et al. 2010

Chem. Commun.

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“…Polymethoxy-1-alkene (58) was isolated from tolytoxin-producing blue-green algae Tolypothrix conglutinate var [95][96][97]. This natural product is a linear carbon chain decorated with isotactic methoxy groups, which makes it challenging synthetic target.…”

Section: Total Synthesis Of Natural Products Using Supersilyl Aldol Rmentioning

confidence: 99%

Supersilyl Protective Groups in Aldol Reactions

Brady

Yamamoto

2013

Modern Methods in Stereoselective Aldol Reactions

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Isotactic polymethoxy 1-alkenes from blue-green algae. Synthesis and absolute stereochemistry

Cited by 55 publications

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High-Resolution Magic Angle Spinning Nuclear Magnetic Resonance of Intact Zebrafish Embryos Detects Metabolic Changes Following Exposure to Teratogenic Polymethoxyalkenes from Algae

High-Resolution Magic Angle Spinning Nuclear Magnetic Resonance of Intact Zebrafish Embryos Detects Metabolic Changes Following Exposure to Teratogenic Polymethoxyalkenes from Algae

Click-based synthesis and proteomic profiling of lipstatin analogues

Supersilyl Protective Groups in Aldol Reactions

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