Article
Chemistry, Organic
Manda Sathish, Fabiane M. Nachtigall, Leonardo S. Santos
Summary: In this study, an efficient enantioselective imine reduction method was developed using in situ generated Fethiosquaramides catalysts (Fe-TSQs) 3a and 3b, resulting in the synthesis of chiral tetrahydro-beta-carbolines.
Article
Chemistry, Organic
Mingdong Jiao, Xianjie Fang
Summary: A novel synthesis of homoallylic nitriles via cobalt-catalyzed hydrocyanation of methylenecyclopropanes is described. The protocol demonstrates excellent selectivity, mild reaction conditions, good functional group compatibility, gram-scale reaction, and product transformations. The extraordinary selectivity is probably attributed to the stronger aptitude of the alkyl-cobalt cyanide intermediate for reductive elimination rather than beta-hydride elimination.
Article
Chemistry, Inorganic & Nuclear
Danila O. Zakharov, Konstantin Chernichenko, Kristina Sorochkina, Timo Repo, Vladimir V. Zhivonitko
Summary: Parahydrogen-induced polarization is a nuclear spin hyperpolarization technique used to enhance NMR signals for catalytic hydrogenation reactions and study their mechanisms. This study presents a PHIP investigation of metal-free imine hydrogenation using the ansa-aminoborane catalyst QCAT, discussing the mechanism and reversibility of the catalytic cycle.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Organic
Jihui Gao, Jie Ni, Rongrong Yu, Gui-Juan Cheng, Xianjie Fang
Summary: This highly regioselective nickel-based catalyst system enables the isomerization/hydrocyanation of aliphatic internal olefins, providing a variety of aliphatic nitriles with excellent regioselectivities and good yields under mild conditions. The reaction protocol, under Lewis acid-free conditions, shows broad functional group tolerance, including secondary amine and unprotected alcohol groups.
Article
Chemistry, Organic
Ying Ding, Jinguo Long, Xianjie Fang
Summary: A nickel-catalyzed hydrocyanation of aliphatic allenes with excellent regioselectivity has been developed. This protocol features mild reaction conditions and good functional group tolerance, providing an efficient catalytic pathway to access various allylic nitriles containing quaternary carbon centers in a one-step fashion. Additionally, preliminary attempts were made to investigate an asymmetric version of this reaction.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Qi Chen, Bo-Bo Li, Lilan Zhang, Xin-Ru Chen, Xin-Xin Zhu, Fei-Fei Chen, Min Shi, Chun-Chi Chen, Yu Yang, Rey-Ting Guo, Weidong Liu, Jian-He Xu, Gao-Wei Zheng
Summary: An engineered IRED with significantly improved activity and stability was developed through three rounds of evolution. The use of this engineered enzyme allowed for complete reduction of a cyclic imine, resulting in high yield and high enantiomeric excess of an important chiral intermediate.
Article
Chemistry, Organic
Geraldo Duran-Camacho, J. Caleb Hethcox
Summary: A nickel-catalyzed cyanation reaction of (hetero)aryl halides using bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane (DABAL-Me3) as a soluble reductant has been developed. The reaction utilizes readily available and inexpensive precatalyst Ni(dppf)Cl2, substoichiometric amount of Zn(CN)2, and DABAL-Me3 as an alternative to insoluble reductants. The addition of catalytic tetrabutylammonium bromide (TBABr) aids in dissolving low levels of the cyanide salt for a completely homogeneous reaction mixture.
Article
Chemistry, Organic
Andrew J. Greenlee, Heyu Chen, Chloe I. Wendell, Jeffrey S. Moore
Summary: This study demonstrates the preparation of a three-rung molecular ladder 8 in one pot via tandem reactions, and investigates its assembly and disassembly, showing that catalyst VI is effective but susceptible to deactivation by hydrolysis and ligand exchange.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Andrew J. Greenlee, Heyu Chen, Chloe Wendell, Jeffrey S. Moore
Summary: A three-rung molecular ladder 8 was synthesized through tandem imine condensation and alkyne metathesis in one pot. Catalyst VI successfully catalyzed the conversion of imine-bearing substrate 7, while catalyst III did not show activity. The susceptibility of catalyst VI to deactivation by hydrolysis and ligand exchange was demonstrated. The assembly and disassembly of ladder 8 in one pot were achieved with and without a Lewis acid catalyst.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tingting Liu, Zefei Xu, Jinhui Feng, Shanshan Yu, Min Wang, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: Two enantiocomplementary imine reductases (IREDs) with high enantioselectivity were identified through screening and engineering, which allowed the synthesis of a series of 1-heteroaryl tetrahydroisoquinolines with high to excellent ee values and isolated yields, providing an effective method for constructing pharmaceutically important alkaloids, including the intermediate of kinase inhibitor TAK-981.
Article
Chemistry, Organic
Tingting Liu, Zefei Xu, Jinhui Feng, Shanshan Yu, Min Wang, Peiyuan Yao, Qiaqing Wu, Dunming Zhu
Summary: Two highly enantioselective enantiocomplementary imine reductases (IREDs) were discovered through screening and enzyme engineering, which exhibited catalytic activity towards the reduction of 1-heteroaryl dihydroisoquinolines. By utilizing (R)-IR141-L172M/Y267F and (S)-IR40, a series of different 1-heteroaryl tetrahydroisoquinolines were efficiently synthesized with excellent enantioselectivity (82 to >99% ee) and high isolated yields (80 to 94%), providing an effective method for constructing pharmaceutically important alkaloids, including the intermediate of kinase inhibitor TAK-981.
Article
Chemistry, Multidisciplinary
Amelia K. Gilio, Thomas W. Thorpe, Nicholas Turner, Gideon Grogan
Summary: The synthesis of chiral amines through the reductive amination reaction is a significant reaction in synthetic chemistry, with applications in pharmaceutical and bioactive molecule synthesis. While transition metal catalysis is commonly used, biocatalytic methods have gained interest due to their selectivity and sustainability. The discovery of imine reductase and reductive aminase enzymes has paved the way for an industrial approach to chiral amine production, enabling scale-up from laboratory to ton-scale reactions.
Article
Chemistry, Organic
Joss Pepe Strache, Lukas Muenzer, Andreas Adler, Dirk Blunk, Hans-Guenther Schmalz
Summary: We investigated the enantioselective Ni-catalyzed hydrocyanation of 1,3-diarylpropenes. A series of (E)-homostilbenes were prepared by Pd-catalyzed coupling, and the hydrocyanation of various homostilbenes was studied using a Ni(cod)2/TADDOL-derived chiral phosphine-phosphite ligand catalyst system. The methodology was applied in a short synthesis of a colchicine analogue, and the absolute configuration of 2,4-diphenylbutyronitrile was determined by comparing experimental and calculated ECD spectra.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Mengyao Tang, Huanchao Gu, Shunlong He, Subramani Rajkumar, Xiaoyu Yang
Summary: An efficient protocol for kinetic resolution of tertiary alcohols has been developed via unprecedented asymmetric enamide-imine tautomerism process enabled by chiral phosphoric acid catalysis. This method is particularly effective for a series of 1,1-dialkyl substituted allyl alcohols, producing chiral tertiary alcohols that are difficult to access through other asymmetric methods. Facile and versatile transformations of the chiral products demonstrate the value of this kinetic resolution method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Nanoscience & Nanotechnology
Jiyun Hu, Federica Zanca, Gregory J. McManus, Isabella A. Riha, Huong Giang T. Nguyen, William Shirley, Collin G. Borcik, Benjamin J. Wylie, Mourad Benamara, Roger D. van Zee, Peyman Z. Moghadam, Hudson Beyzavi
Summary: Chemists have been continuously seeking new linkages for covalent organic frameworks (COFs) as they form the foundation for the materials' structure and properties. A novel strategy using H3PO3 as a bifunctional catalyst was reported to achieve amine-linked COFs from easily obtainable amine and aldehyde linkers. The amine-linked COF was found to outperform its imine analogue in promoting Knoevenagel condensation due to its more basic sites and higher stability.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Applied
Sudarat Khadsai, Noppadol Seeja, Metha Rutnakornpituk, Tirayut Vilaivan, Maliwan Nakkuntod, Waroon Suwankitti, Filip Kielar, Boonjira Rutnakornpituk
Summary: In this study, DNA enrichment of the zein gene from maize was achieved using PNA immobilized on a magnetic solid support. The PNA-functionalized MNP showed high binding specificity with complementary DNA, yielding positive results in gel electrophoresis. This system has the potential to be an effective method for DNA enrichment from various samples.
Article
Biophysics
Chawin Srisomwat, Abdulhadee Yakoh, Anchalee Avihingsanon, Natthaya Chuaypen, Pisit Tangkijvanich, Tirayut Vilaivan, Orawon Chailapakul
Summary: The study proposes a sensitive POCT sensing platform for HIV/HCV cDNA detection based on ACEL technique. The detection of DNA in a label-free format was achieved through the hybridization of probes with DNA targets. The developed device successfully detected HIV/HCV cDNA in healthy human serum, demonstrating its feasibility for cDNA detection in real biological samples.
BIOSENSORS & BIOELECTRONICS
(2022)
Article
Chemistry, Organic
Supanat Buntasana, Jun Hayashi, Prakorn Saetung, Piyatida Klumphu, Tirayut Vilaivan, Panuwat Padungros
Summary: Aqueous-phase ozonolysis is an important process during cloud and fog formation in the atmosphere. This study demonstrates the use of surfactants to assist the ozonolysis of alkenes in water, mitigating foaming and obtaining desired carbonyl products in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Marie Hoarau, Nattida Suwanakitti, Thaveechai Varatthan, Ratthiya Thiabma, Roonglawan Rattanajak, Netnapa Charoensetakul, Emily K. Redman, Tanatorn Khotavivattana, Tirayut Vilaivan, Yongyuth Yuthavong, Sumalee Kamchonwongpaisan
Summary: In this study, a three-step screening of antifolate compounds was carried out against PfHPPK, leading to the identification of 14 active compounds. Molecular docking revealed their binding modes with competitive binding to the HMDP substrate, and in vitro assessments showed low toxicity and good metabolic stability. The most active compounds displayed low micromolar IC50 against drug-resistant parasites, indicating their potential as starting points for inhibitor development against PfHPPK.
Article
Chemistry, Organic
Woraluk Mansawat, Phanomsak Yukhet, Worawan Bhanthumnavin, Oliver Reiser, Tirayut Vilaivan
Summary: The use of C-2-symmetrical chiral amino alcohol ligands in combination with CuCl2 has been shown to be effective for the asymmetric acylation of dI-hydrobenzoins, with up to 99% ee obtained for the monoacylated products.
Editorial Material
Public, Environmental & Occupational Health
Tirayut Vilaivan
Summary: The Grignard reaction has been a versatile tool for synthetic organic chemists for over a century. Recent studies have shown that the reaction can be performed under ambient conditions using ball-milling, making it highly appealing for a wide synthetic community.
ACS CHEMICAL HEALTH & SAFETY
(2022)
Article
Multidisciplinary Sciences
Kotchakorn Supabowornsathit, Kriangsak Faikhruea, Boonsong Ditmangklo, Theeranuch Jaroenchuensiri, Sutthida Wongsuwan, Sirikarn Junpra-ob, Ilada Choopara, Tanapat Palaga, Chanat Aonbangkhen, Naraporn Somboonna, Jaru Taechalertpaisarn, Tirayut Vilaivan
Summary: Novel dicationic styryl dyes with enhanced optical properties and binding affinity towards target nucleic acids have been designed. These dyes show potential applications in colorimetric detection of DNA in vitro and imaging of cellular nucleic acids.
SCIENTIFIC REPORTS
(2022)
Article
Chemistry, Applied
Medena Noikham, Chawallak Sriwiphasathit, Khatcharin Siriwong, Tirayut Vilaivan
Summary: A series of D-pi-A fluorescent styryl pyrene probes were synthesized through the Wittig reaction, and the introduction of electron-withdrawing substituents resulted in solvent-dependent intramolecular charge transfer and solvatochromic properties. The nitro and aldehyde substituents exhibited remarkable sensitivity to environment polarity.
Article
Chemistry, Analytical
Atchara Lomae, Pattarachaya Preechakasedkit, Orakan Hanpanich, Tugba Ozer, Charles S. Henry, Atsushi Maruyama, Ekawat Pasomsub, Angsana Phuphuakrat, Sirirat Rengpipat, Tirayut Vilaivan, Orawon Chailapakul, Nipapan Ruecha, Nattaya Ngamrojanavanich
Summary: The COVID-19 pandemic has accelerated the development of portable diagnostic tools for detecting and controlling the spread of the disease. In this study, a smartphone-assisted Sensit Smart potentiostat was combined with a paper-based electrochemical sensor to detect SARS-CoV-2. The sensor utilized a disposable paper-based device with a modified working electrode that captures the target DNA. The developed sensor demonstrated high specificity and achieved accurate detection of SARS-CoV-2 in patient samples.
Article
Chemistry, Analytical
Manivannan Kalavathi Dhinakaran, Barry Lee Smith, Tirayut Vilaivan, Simon Maher, Thanit Praneenararat
Summary: A fluorescent array based on cyanostilbene was synthesized on a cellulose paper surface to rapidly detect biogenic amines released from spoiled meats. The high-throughput nature of this method revealed highly responsive molecules and offered flexibility in sensing applications. This study provides a robust and cost-effective tool for monitoring meat freshness.
Article
Chemistry, Analytical
Khanut Chittuam, Sakda Jampasa, Tirayut Vilaivan, Pisit Tangkijvanich, Natthaya Chuaypen, Anchalee Avihingsanon, Mohini Sain, Yosita Panraksa, Orawon Chailapakul
Summary: In this study, a novel electrochemical capillary-driven microfluidic DNA sensor was proposed to combine the advantages of static and flow-based detection systems. The integrated system showed good performance in terms of limits of detection and quantification for HIV-1 and HCV detection.
ANALYTICA CHIMICA ACTA
(2023)
Article
Chemistry, Analytical
Sarida Naorungroj, Chawin Srisomwat, Wisarut Khamcharoen, Sakda Jampasa, Ekawat Pasomsub, Kwanwoo Shin, Tirayut Vilaivan, Orawon Chailapakul
Summary: The COVID-19 pandemic caused by SARS-CoV-2 is a significant global health issue. This study developed an electrochemical assay based on G-quadruplex DNAzyme integrated with a microfluidic device for the rapid and accurate detection of SARS-CoV-2 DNA. The assay showed high selectivity, good detection limit, and results in agreement with the standard RT-PCR method within 20 minutes, making it a desirable point-of-care tool for COVID-19 diagnosis.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Analytical
Sureerat Makmuang, Anupun Terdwongworakul, Tirayut Vilaivan, Simon Maher, Sanong Ekgasit, Kanet Wongravee
Summary: Weedy rice is a difficult weed to manage in rice-growing regions, as it is hard to distinguish from cultivated rice. This study proposes a novel classification approach using artificial neural networks and near-infrared hyperspectral imaging to directly discriminate weedy rice. The method showed high accuracy in classifying weedy rice samples.
MICROCHEMICAL JOURNAL
(2023)
Review
Biochemistry & Molecular Biology
Chaturong Suparpprom, Tirayut Vilaivan
Summary: Peptide nucleic acid (PNA) is a synthetic DNA mimic that can recognize complementary nucleic acid strands with high affinity and specificity. The rational design of new generation PNAs with conformational constraints has shown promise in improving their performance. The application of conformationally rigid PNAs in various fields has also yielded significant results.
RSC CHEMICAL BIOLOGY
(2022)
Article
Nanoscience & Nanotechnology
Kriangsak Faikhruea, Ilada Choopara, Naraporn Somboonna, Wanchai Assavalapsakul, Byeang Hyean Kim, Tirayut Vilaivan
Summary: Single-stranded peptide nucleic acid (PNA) probes interact strongly with nanomaterials, and the interaction can be enhanced by electrostatic effects. This study demonstrates that electrostatic effects substantially enhance the quenching of dye-labeled PNA probes by several nanomaterials, and establishes fluorescence and colorimetric assays for DNA and RNA with improved sensitivity.
ACS APPLIED BIO MATERIALS
(2022)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
