Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules

Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules

Catal. Sci. Technol., 2017, Advance Article
DOI: 10.1039/C7CY01130J, Paper

Kazuto Suzuki, Joshua Kyle Stanfield, Osami Shoji, Sota Yanagisawa, Hiroshi Sugimoto, Yoshitsugu Shiro, Yoshihito Watanabe
The benzylic hydroxylation of non-native substrates was catalysed by cytochrome P450BM3, wherein “decoy molecules” controlled the stereoselectivity of the reactions.

From the journal:

• Catalysis Science & Technology

Control of stereoselectivity of benzylic hydroxylation catalysed by wild-type cytochrome P450BM3 using decoy molecules

Kazuto Suzuki,^a  Joshua Kyle Stanfield,^a  Osami Shoji,*^ab  Sota Yanagisawa,^a  Hiroshi Sugimoto,^bc Yoshitsugu Shiro^d  and  Yoshihito Watanabe*^e 

Abstract

The hydroxylation of non-native substrates catalysed by wild-type P450BM3 is reported, wherein “decoy molecules”, i.e., native substrate mimics, controlled the stereoselectivity of hydroxylation reactions. We employed decoy molecules with diverse structures, resulting in either a significant improvement in enantioselectivity or clear inversion of stereoselectivity in the benzylic hydroxylation of alkylbenzenes and cycloalkylbenzenes. For example, supplementation of wild-type P450BM3 with 5-cyclohexylvaleric acid-L-phenylalanine (5CHVA-Phe) and Z-proline-L-phenylalanine yielded 53% (R) ee and 56% (S) ee for indane hydroxylation, respectively, although 16% (S) ee was still observed in the absence of any additives. Moreover, we performed a successful crystal structure analysis of 5CHVA-L-tryptophan-bound P450BM3 at 2.00 Å, which suggests that the changes in selectivity observed were caused by conformational changes in the enzyme induced by binding of the decoy molecules.

M2

Kazuto Suzuki

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suzuki.kazuto*c.mbox.nagoya-u.ac.jp

Yoshihito Watanabe

yoshi*nucc.cc.nagoya-u.ac.jp

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Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C-C coupling reactions

Green Chemistry International

Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C-C coupling reactions

Green Chem., 2017, 19,2931-2935
DOI: 10.1039/C7GC00789B, Communication

O. N. Chupakhin, A. V. Shchepochkin, V. N. Charushin
A simple and efficient electrochemical method for the synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp²)-H bond in azaaromatics with fragments of (hetero)aromatic nucleophiles has been developed

From the journal:

Green Chemistry

Atom- and step-economical nucleophilic arylation of azaaromatics via electrochemical oxidative cross C–C coupling reactions

O. N. Chupakhin,*^ab  A. V. Shchepochkin^ab  and  V. N. Charushin^ab 

*Corresponding authors

^aInstitute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russia
E-mail: chupakhin@ios.uran.ru

^bUral Federal University, 19 Mira Street, 620002 Ekaterinburg, Russia

Abstract

The synthesis of asymmetrical bi(het)aryls through direct functionalization of the C(sp²)–H…

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Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Green Chemistry International

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC00659D, Paper

Weiqiang Yu, Fang Lu, Qianqian Huang, Rui Lu, Shuai Chen, Jie Xu
A potential diesel fuel additive, dimethoxyethane, was highly selectively produced via etherification of crude ethylene glycol over SAPO-34

From the journal:

Green Chemistry

Selective synthesis of dimethoxyethane via directly catalytic etherification of crude ethylene glycol

Weiqiang Yu,^a  Fang Lu,*^a  Qianqian Huang,^ab  Rui Lu,^ab  Shuai Chen^a  and  Jie Xu*^a 

*Corresponding authors

^aState Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian National Laboratory for Clean Energy, Dalian 116023, P. R. China
E-mail:xujie@dicp.ac.cn, lufang@dicp.ac.cn

^bUniversity of the Chinese Academy of Sciences, Beijing 100049, P. R. China

Abstract

Etherification of ethylene…

View original post 148 more words

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

Green Chemistry International

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

Green Chem., 2017, 19,2762-2767
DOI: 10.1039/C7GC00513J, Communication

Hannelore Konnerth, Martin H. G. Prechtl
N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1-3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs).

http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C7GC00513J?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

From the journal:

Green Chemistry

Selective hydrogenation of N-heterocyclic compounds using Ru nanocatalysts in ionic liquids

Hannelore Konnerth^a  and  Martin H. G. Prechtl*^a 

*Corresponding authors

^aDepartment of Chemistry, Institute of Inorganic Chemistry, University of Cologne, Greinstraße 6, 50939 Cologne, Germany
E-mail:martin.prechtl@uni-koeln.de
Web: http://catalysis.uni-koeln.de;www.h2.bio
Fax: +49 221 4701788

Abstract

N-Heterocyclic compounds have been tested in the selective hydrogenation catalysed by small 1–3 nm sized Ru nanoparticles (NPs) embedded in various imidazolium based ionic liquids (ILs). Particularly a diol-functionalised IL shows the best performance in the hydrogenation of quinoline to 1,2,3,4-tetrahydroquinoline…

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Is water a suitable solvent for the catalytic amination of alcohols?

Green Chemistry International

Is water a suitable solvent for the catalytic amination of alcohols?

Green Chem., 2017, 19,2839-2845
DOI: 10.1039/C7GC00422B, Paper

Johannes Niemeier, Rebecca V. Engel, Marcus Rose
The catalytic aqueous-phase amination of biogenic alcohols with solid catalysts is reported for future development of renewable amine value-added chains.

From the journal:

Green Chemistry

Is water a suitable solvent for the catalytic amination of alcohols?

Johannes Niemeier,^a  Rebecca V. Engel^ab  and  Marcus Rose*^a 

*Corresponding authors

^aInstitut für Technische und Makromolekulare Chemie, RWTH Aachen University, Worringerweg 2, 52074 Aachen, Germany
E-mail:rose@itmc.rwth-aachen.de

^bCardiff Catalysis Institute, Cardiff University, 42 Park Place, CF10 3AT Cardiff, UK

Abstract

The catalytic conversion of biomass and biogenic platform chemicals typically requires the use of solvents. Water is present already in the raw materials and in most cases a suitable solvent for the typically highly polar substrates…

View original post 115 more words

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

Green Chemistry International

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

Green Chem., 2017, Advance Article
DOI: 10.1039/C7GC01289F, Paper

Zhanhui Yang, Zhongpeng Zhu, Renshi Luo, Xiang Qiu, Ji-tian Liu, Jing-Kui Yang, Weiping Tang
A highly efficient iridium catalyst is developed for the chemoselective reduction of aldehydes to alcohols in water, using formic acid as a reductant.

From the journal:

Green Chemistry

Iridium-catalyzed highly efficient chemoselective reduction of aldehydes in water using formic acid as the hydrogen source

Zhanhui Yang,^ab  Zhongpeng Zhu,^ac  Renshi Luo,^ad  Xiang Qiu,^a  Ji-tian Liu,^a  Jing-Kui Yang^c  and Weiping Tang*^ae 

*Corresponding authors

^aSchool of Pharmacy, University of Wisconsin–Madison, Madison, USA
E-mail:weiping.tang@wisc.edu

^bFaculty of Science, Beijing University of Chemical Technology, Beijing, P. R. China

^c

View original post 259 more words

A Convenient and “Greener” Synthesis of Methyl Nitroacetate

Methyl Nitroacetate (2)

Warning: Although no incidents occurred, the intermediates generated, as well as the end product, are energetic and should be handled as if they are explosive materials. It is essential that all reactions be conducted behind a blast shield and that proper protective equipment, including a face shield, be worn at all times during the operation.

A new procedure for the synthesis and isolation of methyl nitroacetate is described. The previously published method required drying the explosive dipotassium salt of nitroacetic acid in a vacuum desiccator, followed by grinding this material into a fine powder with a mortar and pestle prior to esterification. To obtain the desired product, benzene was employed as the extraction solvent, sodium sulfate was used as the drying agent, and two distillations were required. The new procedure eliminates drying and grinding of the explosive dipotassium salt, employs ethyl acetate or dichloromethane as the extraction solvent, eliminates the need for a drying agent, and requires a single distillation to furnish the end product in high yield and purity.

clear colorless liquid, bp 65 °C (3.9 Torr).

1H NMR (400 MHz; CDCl3) δ 5.18 (s, 2H), 3.87 (s, 3H);

13C NMR (100 MHz, CDCl3) δ 162.5, 76.2, 53.6;

IR (neat): 3041, 2967, 1751, 1557;

Tdec= 251 °C (onset), 272 °C (peak).

NMR PREDICT

A Convenient and “Greener” Synthesis of Methyl Nitroacetate

Eric C. Johnson†, Pablo E. Guzmán*†, Leah A. Wingard†, Jesse J. Sabatini*† , and Rose A. Pesce-Rodriguez‡

†Energetics Technology Branch, ‡Energetic Materials Science Branch, U.S. Army Research Laboratory, Aberdeen Proving Ground, Maryland 21005, United States

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/acs.oprd.7b00093

 

*E-mail: jesse.j.sabatini.civ@mail.mil. Phone: 410-278-0235., *E-mail: pablo.e.guzman2.civ@mail.mil. Phone: 410-278-8608.

 

NMR predict

 

 

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