Novel 1,2-Dithiins: Synthesis, Molecular Modeling Studies, and Antifungal Activity

Bierer, Donald; Dener, Jeffrey M.; Dubenko, L. G.; Gerber, R. E.; Litvak, Joane; Peterli, S.; Peterli-Roth, P.; Truong, Thien; Mao, Guohua; Bauer, Brigitte

doi:10.1021/jm00014a016

Cited by 55 publications

(23 citation statements)

References 25 publications

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“…However, due to thermochemical safety concerns associated with this approach, an alternative was sought for use on large scale. The commercially available and easily prepared 2,4-hexadiyn-1,6-diol could be silylated to give 62% yield of the monoprotected substrate, with bis-silylated material comprising the balance 20. Regioselective reduction of the unprotected propargylic moiety was achieved using Red-Al in 88% yield.…”

Section: Resultsmentioning

confidence: 99%

An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes

Trost

Livingston

2008

J. Am. Chem. Soc.

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Catalytic ruthenium complexes in conjunction with an indium cocatalyst and Bronsted acid isomerize primary and secondary propargylic alcohols in good yields to provide trans enals and enones exclusively. Readily available indenylbis(triphenylphosphine)ruthenium chloride in the presence of indium triflate and camphorsulfonic acid give the best turnover numbers and reactivity with the broadest range of substrates. Deuterium labeling experiments suggest that the process occurs through propargylic hydride migration followed by protic cleavage of the resultant vinylruthenium intermediate. Application of this method to the synthesis of leukotriene B4 demonstrates its utility and extraordinary selectivity.

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Section: Resultsmentioning

confidence: 99%

An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes

Trost

Livingston

2008

J. Am. Chem. Soc.

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“…The reaction between alcohol 7 and 3-mercaptopropanenitrile ( 8 ) resulted in substitution of bromine to the thiol group and finally the introduction of the thiol functional group. The 3-mercaptopropanenitrile ( 8 ) was synthesized separately in two steps from acrylonitrile or the 3-chloropropanenitrile according to the previously described procedure [48–50]. Next, the obtained compound 9 containing two hydroxy groups and the cyanoethyl protected thiol group was converted into the phosphoramidite being compatible with conditions of solid-phase oligonucleotide synthesis.…”

Section: Resultsmentioning

confidence: 99%

DNA functionalization by dynamic chemistry

Kanlidere¹,

Jochim²,

Cal³

et al. 2016

Beilstein J. Org. Chem.

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SummaryDynamic combinatorial chemistry (DCC) is an attractive method to efficiently generate libraries of molecules from simpler building blocks by reversible reactions under thermodynamic control. Here we focus on the chemical modification of DNA oligonucleotides with acyclic diol linkers and demonstrate their potential for the deoxyribonucleic acid functionalization and generation of libraries of reversibly interconverting building blocks. The syntheses of phosphoramidite building blocks derived from D-threoninol are presented in two variants with protected amino or thiol groups. The threoninol building blocks were successfully incorporated via automated solid-phase synthesis into 13mer oligonucleotides. The amino group containing phosphoramidite was used together with complementary single-strand DNA templates that influenced the Watson–Crick base-pairing equilibrium in the mixture with a set of aldehyde modified nucleobases. A significant fraction of all possible base-pair mismatches was obtained, whereas, the highest selectivity (over 80%) was found for the guanine aldehyde templated by the complementary cytosine containing DNA. The elevated occurrence of mismatches can be explained by increased backbone plasticity derived from the linear threoninol building block as a cyclic deoxyribose analogue.

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“…Nevertheless, it does seem that ␣T is capable of exerting toxic effects on both plants (4,6) and animals (7) in the absence of light. Thiarubrines, related UVA-absorbing compounds produced in the roots of some plants, show lightindependent fungal toxicity that is proposed to result from the reactivity of their 1,2-dithiin ring, possibly with a specific enzyme in the fungus (22,23). However, in the case of nematodes at least, direct interaction of ground-state ␣T with biomolecules in the target organism seems unlikely because only root-penetrating endoparasites are affected, while ectoparasitic and saprozoic forms are unharmed by the presence of ␣T in the unirradiated rhizosphere (7).…”

Section: Discussionmentioning

confidence: 99%

Participation of the Photosensitizer Alpha-terthienyl in thePeroxidase-catalyzed Oxidation of Indole-3-acetic acid†

Brennan

Lee

Battaglia

2000

Photochem Photobiol

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The plant photosensitizer alpha-terthienyl (alpha T) is toxic toward a variety of organisms, and normally requires exposure to ultraviolet-A radiation for activation and singlet molecular oxygen formation. However, some toxicity has also been reported to occur in the dark. One hypothesis that has been proposed to account for this light-independent toxicity is that the sensitizer becomes activated by energy transfer from the excited-state products of enzymatic reactions. We have investigated this hypothesis using the horseradish peroxidase (HRP)-catalyzed oxidation of indole-3-acetic acid (IAA), which generates indole-3-aldehyde in an excited triplet state. Light is emitted during the IAA/HRP reaction at acidic pH, is increased by inclusion of alpha T and is not observed with heat-denatured HRP. The rates of both the oxidation of IAA and the subsidence of light emission are more rapid in the IAA/alpha T/HRP system than with IAA and HRP alone, indicating that the presence of alpha T accelerates the reaction. Bleaching occurs at the wavelength of maximal alpha T absorbance and is promoted by the inclusion of IAA. Readdition of both IAA and alpha T to a spent reaction mixture is required to restore light emission after it has subsided, further suggesting that both are consumed in the reaction. We were unable to detect measurable quantities of singlet molecular oxygen formation in this system. These results do not support the energy transfer hypothesis, but instead are more compatible with a model proposed by Krylov and Chebotareva [Krylov, S. N. and A. B. Chebotareva (1993) FEBS Lett. 324, 6-8] for the co-oxidation of IAA and xanthene dyes.

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Novel 1,2-Dithiins: Synthesis, Molecular Modeling Studies, and Antifungal Activity

Cited by 55 publications

References 25 publications

An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes

An Atom-Economic and Selective Ruthenium-Catalyzed Redox Isomerization of Propargylic Alcohols. An Efficient Strategy for the Synthesis of Leukotrienes

DNA functionalization by dynamic chemistry

Participation of the Photosensitizer Alpha-terthienyl in thePeroxidase-catalyzed Oxidation of Indole-3-acetic acid†

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