- Substrate and inhibitor selectivity, and biological activity of an epoxide hydrolase from Trichoderma reesei
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Epoxide hydrolases (EHs) are present in all living organisms and catalyze the hydrolysis of epoxides to the corresponding vicinal diols. EH are involved in the metabolism of endogenous and exogenous epoxides, and thus have application in pharmacology and biotechnology. In this work, we describe the substrates and inhibitors selectivity of an epoxide hydrolase recently cloned from the filamentous fungus Trichoderma reesei QM9414 (TrEH). We also studied the TrEH urea-based inhibitors effects in the fungal growth. TrEH showed high activity on radioative and fluorescent surrogate and natural substrates, especially epoxides from docosahexaenoic acid. Using a fluorescent surrogate substrate, potent inhibitors of TrEH were identified. Interestingly, one of the best compounds inhibit up to 60% of T. reesei growth, indicating an endogenous role for TrEH. These data make TrEH very attractive for future studies about fungal metabolism of fatty acids and possible development of novel drugs for human diseases.
- de Oliveira, Gabriel S.,Adriani, Patricia P.,Wu, Hao,Morisseau, Christophe,Hammock, Bruce D.,Chambergo, Felipe S.
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p. 371 - 379
(2018/11/23)
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- Synthesis of heterodinuclear hemisalen complexes on a hexaarylbenzene scaffold and their application for the cross-pinacol coupling reaction
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Intermolecular cross-pinacol coupling reaction between aliphatic and aromatic aldehydes by using heterodinuclear hemisalen complexes 1cis with vanadium(V) and titanium(IV) on a hexaarylbenzene scaffold is reported. Our ligand design is based on the individual activation of two aldehydes by vanadium and titanium, which are positioned with a suitable space on the rigid scaffold. Ligands such as 1cis were synthesized by Diels-Alder addition and decarbonylation reaction, followed by condensation of dialdehyde 3cis with various aminophenols. The influence of the substituents on the ligands on the pinacol coupling reaction was investigated. As a result, the reductive coupling reaction between aliphatic and aromatic aldehydes by using a catalytic amount of 1cis in the presence of Me3SiCl and Zn provided the corresponding cross-coupled 1,2-diol in good yields with high cross-selectivity. Working together: Dihemisalen ligands on a hexaaryl benzene scaffold were designed and the heterodinuclear complexes 1cis with vanadium(V) and titanium(IV) were synthesized from the corresponding disalicylaldehyde compound (see scheme). By using the heterodinuclear catalysts, the selective intermolecular cross-pinacol coupling reaction between aliphatic and aromatic aldehydes is demonstrated. Copyright
- Miyasaka, Akihiro,Amaya, Toru,Hirao, Toshikazu
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p. 1615 - 1621
(2014/03/21)
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- Reduction of carbonyl compounds to their corresponding of alcohols with [Zn(BH4)2(2-MeOpy)] & [Zn(BH4) 2(2-Mepy)] as new reducing agents (a comparison study)
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The reduction of a variety of carbonyl compounds was efficiently carried out with [Zn(BH4)2(2-MeOpy)] and [Zn(BH4) 2(2-Mepy)] as new reducing agents. The reduction reactions were performed to give the corresponding alcohols derivatives in perfect yields.
- Khezri, Behrooz,Ghadimi, Farnaz Najaf,Karashi, Chonur Nevisandeh,Setamdideh, Davood
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p. 623 - 629
(2013/11/06)
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- Zn(BH4)2/Al2O3: A new synthetic method for the efficient and convenient reduction of organic carbonyl compounds to their corresponding alcohols
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Zn(BH4)2 (0.5-2 mmol) in the presence of Al 2O3 (1 mmol) reduces a variety of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β-unsaturated carbonyl compounds to their corresponding alcohols. The reduction reactions were realized in THF at room temperature affording high to excellent yields of the products. The chemoselective reduction of aldehydes over ketones was successfully accomplished with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was successfully accomplished.
- Setamdideh, Davood,Khezri, Behrooz,Rahmatollahzadeh, Mehdi
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- Reduction of α-diketones and acyloins with Zn(BH4) 2/ZrCl4 to their corresponding vicinal diols
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α-diketones and acyloins are reduced to the corresponding vicinal diols with Zn(BH4)2/ZrCl4 system in THF at room temperature.
- Kamari, Rasol,Setamdideh, Davood
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p. 497 - 499
(2013/11/06)
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- Convenient reduction of carbonyl compounds to their corresponding alcohols with NaBH4/(NH4)2C2O4 system
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Sodium borohydride (0.4-1.5 equivalents) in the presence of ammonium oxalate (0.2 equivalents) reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α,β- unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in acetonitrile in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was achieved successfully with this reducing system.
- Setamdideh, Davood,Ghahremani, Sahar
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experimental part
p. 91 - 97
(2012/07/14)
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- Mild and efficient reduction of organic carbonyl compounds to their corresponding alcohols with Zn(BH4)2 under protic condition
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Zn(BH4)2 (1-2 mmol) in wet THF or CH3CN reduces varieties of organic carbonyl compounds such as aldehydes, ketones, acyloins, α-diketones and α, β-unsaturated carbonyl compounds to their corresponding alcohols. Reduction reactions were carried out in wet THF at room temperature in high to excellent yields of products. The chemoselective reduction of aldehydes over ketones was accomplished successfully. In addition, regioselectivity and exclusive 1,2-reduction of conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.
- Setamdideh, Davood,Khezri, Behrooz,Rahmatollahzadeh, Mehdi,Poramjad, Avat Ali
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experimental part
p. 3591 - 3596
(2012/07/28)
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- TiO2 as an efficient catalytic surface for reduction of carbonyl compounds with NaBH4 under solvent-free, solid-gel and microwave irradiation
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Structurally different carbonyl compounds such as aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones and acyloins were reduced efficiently by NaBH4/TiO2 system under solvent-free, solid-gel and microwave irradiation. The chemoselective reduction of aldehydes over ketones was achieved successfully by NaBH4/TiO 2 system at solvent-free condition. In addition, regioselectivity and exclusive 1,2-reduction of Conjugated carbonyl compounds to their corresponding allylic alcohols in high to excellent yields was accomplished successfully with this reducing system.
- Setamdideh, Davood,Karimi, Zahra,Rahimi, Fatemeh
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experimental part
p. 1621 - 1634
(2012/06/16)
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- Wet SiO2 as a suitable media for fast and efficient reduction of carbonyl compounds with NABH3CN under solvent-free and acid-free conditions
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Reduction of carbonyl compounds such as aldehydes, ketones, α,β-unsaturated enals and enones, α-diketones and acyloins was carried out readily with NaBH3CN in the presence of wet SiO2 as a neutral media. The reactions were performed at solvent-free conditions in oil bath (70-80 °C) or under microwave irradiation (240 W) to give the product alcohols in high to excellent yields. Regioselective 1,2-reduction of conjugated carbonyl compounds took place in a perfect selectivity without any side product formation.
- Kouhkan, Mehri,Zeynizadeh, Behzad
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experimental part
p. 2961 - 2966
(2012/04/17)
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- Modular asymmetric synthesis of 1,2-diols by single-pot allene diboration/hydroboration/cross-coupling
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Chiral allyl vinyl boronates are generated by catalytic enantioselective diboration of prochiral allenes. They may then be reacted, in situ, with a hydroborating reagent to form a novel triboron intermediate. The least hindered and most reactive C-B bond
- Pelz, Nicholas F.,Morken, James P.
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p. 4557 - 4559
(2007/10/03)
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- Mild and convenient method for reduction of carbonyl compounds with the NaBH4/charcoal system in wet THF
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The NaBH4/C (charcoal) system reduces a variety of carbonyl compounds such as aldehydes, ketones, acyloins and α-diketones to their corresponding alcohols in high to excellent yields. Reduction reactions were carried out in wet THF at r.t. In addition, regioselective 1,2-reduction of α,β-unsaturated aldehydes and ketones was achieved perfectly with this reducing system. By decreasing the amount of aprotic solvent, all reductions took place fast and efficiently under solid-gel condition.
- Setamdideh, Davood,Zeynizadeh, Behzad
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p. 1275 - 1281
(2008/09/18)
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- Titanyl acetylacetonate as an efficient catalyst for regioselective 1,2-reduction of α,β-unsaturated carbonyl compounds and conversion of α-diketones & acyloins to vicinal diols with sodium borohydride
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α,β-Unsaturated aldehydes and ketones were reduced readily and exclusively to their corresponding allylic alcohols with NaBH4 and catalytic amounts of titanyl acetylacetonate at room temperature. Reduction reactions were carried out in CH3CN or THF. This reducing system was also efficient for the reduction of α-diketones and acyloins to their corresponding vicinal diols in CH3CN.
- Zeynizadeh, Behzad
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p. 525 - 530
(2007/10/03)
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- NaBH4/NaHSO4·H2O a heterogeneous acidic system for a mild and convenient reduction of carbonyl compounds under protic condition
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NaBH4 in the presence of sodium bisulfate (NaHSO 4·H2O), a weakly acidic reagent, efficiently reduces a variety of carbonyl compounds such as aldehydes, ketones, α, β-unsaturated aldehydes and ketones, α-diketones and acyloins to their corresponding alcohols in acetonitrile under heterogeneous condition. Reduction reactions were accomplished at room temperature or under reflux condition.
- Zeynizadeh, Behzad,Behyar, Tarifen
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p. 453 - 457
(2007/10/03)
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- Wet THF as a suitable solvent for a mild and convenient reduction of carbonyl compounds with NaBH4
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NaBH4 in wet THF can readily reduce varieties of carbonyl compounds such as aldehydes, ketones, conjugated enones, acyloins, and α-diketones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed at room temperature or under reflux condition. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system.
- Zeynizadeh, Behzad,Behyar, Tarifeh
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p. 307 - 315
(2007/10/03)
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- Water as a green solvent for fast and efficient reduction of carbonyl compounds with NaBH4 under microwave irradiation
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Reduction of varieties of carbonyl compounds such as aldehydes, ketones, α,β-unsaturated aldehydes and ketones, α-diketones and acyloins was carried out very fast and efficiently by sodium borohydride in water under microwave irradiation. The corresponding product alcohols were obtained in high to excellent yields.
- Zeynizadeh, Behzad,Setamdideh, Davood
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p. 1179 - 1184
(2007/10/03)
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- The acid accelerated ruthenium-catalysed dihydroxylation. Scope and limitations
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Recently, we discovered a significant rate acceleration in RuO 4-catalysed dihydroxylations of olefins by addition of Broensted-acids resulting in a reduction of the catalyst loading to only 0.5 mol%. The present paper gives a full account on the optimisation protocol that led to the discovery of the beneficial influence of protic acids. A strong focus is set on the detailed description of the influence of different reaction parameters on both reactivity and selectivity. In the second part an intense investigation of scope and limitations will be presented. The results provided in this manuscript might lead to a deeper understanding of competing processes that influence the selectivity in RuO4-catalysed dihydroxylations.
- Plietker, Bernd,Niggemann, Meike,Pollrich, Anja
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p. 1116 - 1124
(2007/10/03)
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- Ultrasound-promoted reduction of conjugated enones, α-diketones and acyloins with NaBH4 under aprotic condition
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A variety of conjugated enones are reduced regioselectively to their corresponding allylic alcohols with NaBH4 under ultrasound irradiation. Reduction reactions were performed in THF at room temperature and the product alcohols were obtained in high to excellent yields. This system is also efficient for the reduction of α-diketones and acyloins to vicinal diols.
- Zeynizadeh, Behzad,Yahyaei, Saiedeh
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p. 699 - 703
(2007/10/03)
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- NMR studies of three types of highly coordinated organotin hydrides: Chemo-, regio-, and stereoselective reduction of 2,3-epoxy ketones
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Three types of highly coordinated organotin hydrides, Bu2SnIH-Lewis base (Lewis bases; HMPA or tripiperidinophosphine oxide) (type A), Bu2SnFH-HMPA (type B), and Bu3SnH-Bu4NX (X = F, CN) (type C), were characterized as nucleophilic, chelation, and nonchelation types of reductants, respectively, in the reaction with 2,3-epoxy ketones 1. These reagents, which promoted a reduction of the epoxy ring and syn-selective and anti-selective carbonyl reduction, respectively, were spectroscopically confirmed with 1H, 13C, 19F, and 119Sn NMR and FT-IR. Furthermore, the correlations between their structures and selective reducing abilities were discussed.
- Kawakami, Takayo,Shibata, Ikuya,Baba, Akio
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