- Using Small Molecules to Enhance P450 OleT Enzyme Activity in Situ
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Cytochrome P450 OleT is a fatty acid decarboxylase that catalyzes the production of olefins with biofuel and synthetic applications. However, the relatively sluggish catalytic efficiency of the enzyme limits its applications. Here, we report the application of a novel class of benzene containing small molecules to improve the OleT activity. The UV-Vis spectroscopy study and molecular docking results confirmed the high proximity of the small molecules to the heme group of OleT. Up to 6-fold increase of product yield has been achieved in the small molecule-modulated enzymatic reactions. Our work thus sheds the light to the application of small molecules to increase the OleT catalytic efficiency, which could be potentially used for future olefin productions.
- Zhang, Libo,Ma, Dumei,Yin, Yingwu,Wang, Qian
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supporting information
p. 8940 - 8945
(2021/05/28)
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- Synthesis of N-substituted sulfonamides containing perhalopyridine moiety as bio-active candidates
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A series of new halogenated aryl sulfonamides, as bio-active candidates, was synthesized from the reaction of the corresponding aryl sulfonamides with pentafluoro- and pentachloropyridines. Surprisingly, unlike aryl sulfonamides, the reaction of sulfamides with pentafluoro- and pentachloropyridines gave unexpected bis-perfluoro(chloro)pyridin-4-ylamines.
- Hosseini, Raziyeh,Mohammadiannejad, Kazem,Ranjbar-Karimi, Reza
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- Method for preparing chiral amino compound and intermediate thereof
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The invention discloses a method for preparing a chiral amino compound and intermediate thereof. The method comprises the step of performing a deprotection reaction as shown in the specification on acompound in a formula D and mercaptide in a solvent, wherein in the compound in the formula D, X is selected from O or NMe; Y is Me when X is O, and Y is H when X is NMe; n is selected from 0, 1, 2, 3, 4 or 5; each R is independently NO2 or CN; the mercaptide is salt formed by thiol and metal, and is shown as RS-M; M is an alkali metal ion, and is especially selected from one or more of Li, Na, K, Ru and Cs; and R is C14-24 alkyl. The preparation method is simple and convenient to operate, has mild reaction conditions, high yield and high product quality, and is applicableto industrial production.
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Paragraph 0089; 0090-0091
(2018/04/03)
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- A New, Practical One-Pot Synthesis of Unprotected Sulfonimidamides by Transfer of Electrophilic NH to Sulfinamides
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Unprotected tertiary sulfonimidamides have been prepared in good to excellent yields in a one-pot transformation from tertiary sulfinamides through NH transfer. The reaction is mediated by commercially available (diacetoxyiodo)benzene and ammonium carbamate in methanol under convenient conditions. A wide range of functional groups are tolerated and initial results indicate that the NH transfer is stereospecific. A small molecule X-ray analysis of NH sulfonimidamide 2 a and its behavior in selected in vitro assays in comparison to the matched sulfonamide are also reported. This new reaction provides a safe, short and efficient approach to sulfonimidamides, which have been the subject of recent, growing interest in the life sciences.
- Izzo, Flavia,Sch?fer, Martina,Stockman, Robert,Lücking, Ulrich
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supporting information
p. 15189 - 15193
(2017/10/12)
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- Oxidative debenzylation of N-benzyl amides and O-benzyl ethers using alkali metal bromide
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The oxidative debenzylation of N-benzyl amides and O-benzyl ethers was promoted with high efficiency by a bromo radical formed through the oxidation of bromide from alkali metal bromide under mild conditions. This reaction provided the corresponding amides from N-benzyl amides and carbonyl compounds from O-benzyl ethers in high yields.
- Moriyama, Katsuhiko,Nakamura, Yu,Togo, Hideo
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supporting information
p. 3812 - 3815
(2014/08/05)
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- Copper-catalyzed trifluoromethylation and cyclization of aromatic-sulfonyl-group-tethered alkenes for the construction of 1,2-benzothiazinane dioxide type compounds
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A multi-talented system: An efficient copper-catalyzed tandem trifluoromethylation/annulation of an electron-deficient aromatic ring has been developed. This method provides a powerful and straightforward way to synthesize trifluoromethylated 1,2-benzothiazinane dioxides under mild conditions (see scheme). The mechanism was investigated by a series of kinetic experiments and isotopic labeling studies.
- Dong, Xiang,Sang, Rui,Wang, Qiang,Tang, Xiang-Ying,Shi, Min
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supporting information
p. 16910 - 16915
(2014/01/06)
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- Directed ortho -metalation-cross-coupling strategies. One-pot Suzuki reaction to biaryl and heterobiaryl sulfonamides
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A general synthesis of stable ortho-boropinacolato aryl and heteroaryl sulfonamides by directed ortho-metalation (DoM) and either MeOBPin or i-PrOBpin electrophile quench, 3 → 4, is described. A one-pot metalation-Suzuki cross-coupling procedure for the synthesis of biaryls and heterobiaryls, 3 → 5, and a complementary DoM-Ir-catalyzed boronation sequence (Scheme 6) are delineated.
- Schneider, Cedric,Broda, Ellen,Snieckus, Victor
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supporting information; experimental part
p. 3588 - 3591
(2011/10/03)
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- Establishment of heterolytic and homolytic Y-NO2 bond dissociation energy scales of nitro-containing compounds in acetonitrile: Chemical origin of NO2 release and capture
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(Chemical Equation Presented) The first heterolytic and homolytic N(O)-NO2 bond dissociation energy scales of three types Y-nitro (Y = N, O) compounds and corresponding radical anions in acetonitrile were established by using titration calorimetry combined with relevant electrochemical data through proper thermodynamic cycles.
- Li, Xin,Zhu, Xiao-Qing,Zhang, Fan,Wang, Xiao-Xiao,Cheng, Jin-Pei
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p. 2428 - 2431
(2008/09/20)
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- Regioselectivity and the nature of the reaction mechanism in nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzenesulfonates with primary amines
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Second-order rate constants have been measured for the reaction of 2,4-dinitrophenyl X-substituted benzenesulfonates with a series of primary amines. The nucleophilic substitution reaction proceeds through competitive S-O and C-O bond fission pathways. The S-O bond fission occurs dominantly for reactions with highly basic amines or with substrates having a strong electron-withdrawing group in the sulfonyl moiety. On the other hand, the C-O bond fission occurs considerably for the reactions with low basic amines or with substrates having a strong electron-donating group in the sulfonyl moiety, emphasizing that the regioselectivity is governed by both the amine basicity and the electronic effect of the sulfonyl substituent X. The apparent second-order rate constants for the S-O bond fission have resulted in a nonlinear Bronsted-type plot for the reaction of 2,4-dinitrophenyl benzenesulfonate with 10 different primary amines, suggesting that a change in the rate-determining step occurs upon changing the amine basicity. The microscopic rate constants (k1 and k2/k-1 ratio) associated with the S-O bond fission pathway support the proposed mechanism. The second-order rate constants for the S-O bond fission result in good linear Yukawa-Tsuno plots for the aminolyses of 2,4-dinitrophenyl X-substituted benzenesulfonates. However, the second-order rate constants for the C-O bond fission show no correlation with the electronic nature of the sulfonyl substituent X, indicating that the C-O bond fission proceeds through an SNAR mechanism in which the leaving group departure occurs rapidly after the rate-determining step.
- Um, Ik-Hwan,Hong, Jin-Young,Kim, Jung-Joo,Chae, Ok-Mi,Bae, Sun-Kun
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p. 5180 - 5185
(2007/10/03)
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- Arenesulfonylheterocycles (I): Synthesis and reactions of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with amines
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The direct sulfonylation of 4,5-dichloropyridazin-3-ones with some benzenesulfonyl chlorides in the presence of base in tetrahydrofuran gave only the corresponding N-sulfonylated product. The reaction of 2-benzenesulfonyl-4,5-dichloropyridazin-3-ones with some aliphatic amines under neutral conditions afforded 5-alkylamino-2-benzenesulfonyl-4-chloropyridazin-3-ones and/or the corresponding N-alkyl-benzenesulfonamides.
- Kweon, Deok-Heon,Kim, Ho-Kyun,Kim, Jeum-Jong,Chung, Hyun A.,Woo, Song Lee,Kim, Sung-Kyu,Yoon, Yong-Jin
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p. 203 - 211
(2007/10/03)
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- A USEFUL APPROACH TO PRIMARY AMINES
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Smooth reduction of acylsulfonamides to sulfonamides by borane, when coupled to standard sulfonamide cleavage procedures, provides a general route to primary amines.
- Belletire, J. L.,Fry, D. F.
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