Article
Chemistry, Multidisciplinary
Finn Burg, Tomislav Rovis
Summary: A method for the internal and highly diastereoselective amino oxygenation of 1,3-dienes has been developed, catalyzed by a cationic heptamethylindenyl (Ind*) Rh(III) complex, filling the gap in the selective amino oxygenation of 1,3-dienes at the internal position.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Naoki Oku, Tomoya Miura
Summary: A double C(sp3)-H functionalization of ethylarenes with alcohols and N- fluorobenzenesulfonimide is demonstrated. The reaction proceeds in three stages: (1) Cu-catalyzed benzylic alkoxylation of ethylarenes to give 1-(1-alkoxyethyl)benzenes; (2) The resulting 1-(1-alkoxyethyl)benzenes gradually convert into vinylarenes; (3) Cu-catalyzed amino-alkoxylation of the intermediary vinylarenes to yield arylethanolamines. This method introduces C-N and C-O bonds regioselectively at the homobenzylic and benzylic positions of ethylarenes.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hiroto Takahashi, Yuki Nagashima, Ken Tanaka
Summary: The electron-deficient bis(ethoxycarbonyl)-substituted cyclopentadienyl (Cp-E) rhodium(III) complex catalyzes the oxidative intramolecular 1,1-oxyamination of alkenes with N-benzoyl amino acids to produce oxazoloisoindole-2,5-diones. Experimental and theoretical mechanistic studies showed that this oxidative 1,1-oxyamination does not proceed through the aza-Wacker reaction, but involves the formation of a rhoda(III)oxazolidine initiated by carboxylic acid-directed N-H bond cleavage.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yinggao Meng, Manman Song, Yue Wang, Yuxin Wang, Er-Qing Li
Summary: A palladium-catalyzed asymmetric (4 + 3) cycloaddition was developed for the enantioselective synthesis of trifluoromethylated spirooxindoles. The reaction proceeded smoothly in a one-pot manner without the need for a Bronsted base, providing a cost-effective and efficient strategy for the construction of optically pure medium-sized rings.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Inorganic & Nuclear
Aleksa Radovic, Nikki J. Wolford, Hongze Li, William W. Brennessel, Hao Xu, Michael L. Neidig
Summary: This study focuses on the ligand effects on reactivity and in situ iron speciation in the iron-catalyzed amino-oxygenation of olefins using a bisoxazoline ligand. Experimental results reveal that the ligand and solvent have significant influence on the speciation in the precatalytic mixture, leading to the formation of different species that affect the reactivity. The in situ experiments provide evidence for the formation of an iron iminyl radical species and suggest that the functionalized hydroxylamine identity can dictate the reactivity observed in these reactions.
Article
Chemistry, Organic
Kirsten A. Hewitt, Claire A. Herbert, Elizabeth R. Jarvo
Summary: A nickel-catalyzed intramolecular conjunctive cross-electrophile coupling reaction has been developed for the synthesis of 3,5-vicinal carbocyclic rings found in various biologically active compounds and natural products. Mechanistic experiments suggest that the reaction proceeds through alkyl iodides formed in situ, initiates at the secondary electrophilic center, and proceeds via radical intermediates.
Article
Chemistry, Multidisciplinary
Anthony F. Tierno, Jennifer C. Walters, Andres Vazquez-Lopez, Xiao Xiao, Sarah E. Wengryniuk
Summary: This study utilizes N-HVI reagents as heterocyclic group transfer reagents to provide a broad scope of N-alkyl(heteroaryl)onium salts via aminolactonization of alkenoic acids, showcasing a novel method for their synthesis.
Article
Chemistry, Multidisciplinary
Chisato Wata, Takuya Hashimoto
Summary: Metal-free, catalytic enantioselective intermolecular oxyamination of alkenes is achieved using organoiodine(I/III) chemistry. The reaction shows high enantioselectivity and electronically controlled regioselectivity with aryl- and alkyl-substituted alkenes. Key to the success is the discovery of N-(fluorosulfonyl) carbamate as a bifunctional N,O-nucleophile, allowing easy deprotection to yield free amino alcohols without loss of enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Xiao-Dong Liu, Qiu-An Wang, Yan-Ping Zhu, Zhi-Hong Peng, Jin-Heng Li
Summary: This study presents a new copper-catalyzed method for the aerobic hydroxyamination of unsaturated keto oximes with O-2 in EtOH, producing functionalized cyclic nitrones. The method is characterized by its easy operation, discharge of water as a byproduct, use of green molecular oxygen as the oxygen atom source and terminal oxidant, inexpensive copper salt as the catalyst, low-cost environmentally friendly ethanol as the medium, and excellent selectivity, broad substrate scope, and functional group tolerance.
Article
Chemistry, Multidisciplinary
Ningxin Xu, Ziyin Kong, Johnny Z. Wang, Gabriel J. Lovinger, James P. Morken
Summary: This study discovered that a neighboring boronate group in the substrate can accelerate transmetalation to copper, enabling site-selective cross-couplings of organoboronic esters. The method is practical and allows for coupling between vicinal bis(boronic esters) and allyl, alkynyl, propargyl electrophiles, and simple protons. Mechanistic experiments suggest the involvement of chelated cyclic ate complexes in transmetalation.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Maorui Wang, Chengqian Zhang, Chenggang Ci, Huanfeng Jiang, Pierre. H. Dixneuf, Min Zhang
Summary: Despite the challenges, we have successfully developed a room temperature approach for the direct construction of alpha-hydroxyalkyl cyclic amines through the strategy of electroreductive alpha-hydroxyalkylation. This method offers a broad substrate scope, simplicity in operation, high chemoselectivity, and does not require pressurized H2 gas or transition metal catalysts. The activation of reactants by the zinc ion generated from anode oxidation plays a crucial role in this transformation. This strategy, combined with substrate activation by Lewis acids, is expected to lead to the development of more useful transformations.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Chisato Wata, Takuya Hashimoto
Summary: The enantioselective intramolecular oxyaminations were achieved by utilizing benzyl N-(fluorosulfonyl)carbamate as the exogenous nitrogen source in Organoiodine-catalyzed reactions. This method allows the formation of enantioenriched lactones and oxazolines from gamma,delta- and delta,epsilon-unsaturated esters and N-allyl amides.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Yunquan Man, Shiwen Liu, Bo Xu, Xiaojun Zeng
Summary: A method of N-fluorocarboxamide-directed N-heterocyclic-carbene (NHC)-catalyzed benzylic C-H acylation with aldehydes via the hydrogen atom transfer strategy is disclosed. This method involves a sequence of single-electron transfer, 1,5-hydrogen atom transfer, and radical cross-coupling steps, providing facile access to various highly functionalized ketones with good chemical yields and functional group tolerance.
Article
Chemistry, Organic
Kun She, Feng Liang, Shichao Tian, Hengshan Wang, Gavin Chit Tsui, Quande Wang
Summary: An N-hetercyclic carbene-catalyzed three-component acyldifluoromethylation reaction has been developed, providing a practical route for the synthesis of pharmaceutically relevant compounds without the need for transition metals or photocatalysts. Late-stage acyldifluoromethylation of drug analogues was also successfully demonstrated in this study. The reaction utilizes NaSO2CF2H as the source of the CF2H radical with an oxidant for radical relay.
Article
Chemistry, Organic
Tong -Yang Cao, Lin Qi, Wei Dong, Zhi-Min Yan, Shi-Chao Ji, Jian-Long Du, Linlin Zhang, Wei Li, Li-Jing Wang
Summary: In this study, we developed a NIS-promoted selective amino-diazidation and amino-iodoazidation reaction method, which allows the direct synthesis of compounds containing multiple nitrogen moieties in one step. The method is metal-free and offers excellent functional group compatibility and mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Andy Pranata, Blake Curtis, Christopher C. Waller, Karen Caldwell, Paul W. Zahra, Steven L. Karamatic, Malcolm D. McLeod
Summary: Samples of the 'dietary supplement' Furazadrol sourced through the internet have been reported to contain designer anabolic androgenic steroids, raising concerns over potential abuse in sports. Metabolism of Furazadrol in greyhounds revealed key urinary metabolites that can aid anti-doping laboratories in regulating greyhound racing.
DRUG TESTING AND ANALYSIS
(2021)
Article
Endocrinology & Metabolism
Carl Jenkinson, Reena Desai, Malcolm D. McLeod, Jonathan Wolf Mueller, Martin Hewison, David J. Handelsman
Summary: This study analyzed the contribution of sulfate and glucuronide vitamin D metabolites relative to unconjugated levels in human serum. The results showed that sulfate conjugates formed a higher proportion of circulating vitamin D metabolites compared to glucuronide conjugates. The findings suggest that a combination of both conjugated and unconjugated measurements may provide a more accurate assessment of vitamin D status.
JOURNAL OF CLINICAL ENDOCRINOLOGY & METABOLISM
(2022)
Article
Biochemistry & Molecular Biology
Christopher C. J. Fitzgerald, Rikard Hedman, Dimanthi R. Uduwela, Bettina Paszerbovics, Adam J. Carroll, Teresa Neeman, Adam Cawley, Lance Brooker, Malcolm D. McLeod
Summary: The study introduces a new workflow for untargeted metabolic profiling of sulfated metabolites in urine. The method utilizes high-performance liquid chromatography and mass spectrometry coupled with data dependent acquisition for analysis. The utility of the method is demonstrated in two applications: examining the urinary metabolome of a thoroughbred horse after administration of a steroid and studying the hydrolytic activity of sulfatase enzymes on human urine. The method provides a rapid tool for systematic profiling of sulfated metabolites in urine.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Engineering, Chemical
Momodou Salieu Sowe, Arda Rista Lestari, Eka Novitasari, Masruri Masruri, Siti Mariyah Ulfa
Summary: In this study, Ni catalysts supported on silica-zirconia and aluminazirconia binary oxides were synthesized and used for the hydrodeoxygenation of waste cooking oil to produce green diesel. The results showed that reaction time influenced the selectivity of the reaction products, and both catalysts exhibited promising hydrodeoxygenation activity towards n-C-15 hydrocarbon.
BULLETIN OF CHEMICAL REACTION ENGINEERING AND CATALYSIS
(2022)
Article
Chemistry, Organic
Komba Thomas, Olha Khymenets, Oscar J. Pozo, Malcolm D. McLeod
Summary: The convenient synthesis of two 3-glucuronide conjugates as long-term markers for endogenous androgenic anabolic steroid abuse in doping control studies is reported. These markers are resistant to enzymatic hydrolysis, which may result in them being missed by conventional GC-MS analysis protocols.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemical Research Methods
Christopher C. J. Fitzgerald, Christopher Bowen, Madysen Elbourne, Adam Cawley, Malcolm D. McLeod
Summary: The identification and confirmation of steroid sulfate metabolites in biological samples are crucial in anti-doping analysis and clinical sciences. This study utilized energy-resolved collision-induced dissociation to distinguish isomeric steroid sulfate compounds and guide the synthesis of reference materials for unambiguous confirmation of a steroid sulfate biomarker.
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY
(2022)
Article
Biochemistry & Molecular Biology
Bradley J. Stevenson, Andy Pranata, Malcolm D. McLeod
Summary: Steroid sulfate esters are important metabolites for various fields. Researchers used directed evolution to discover a variant, DRN-PaS, capable of efficiently hydrolyzing alpha-configured steroid sulfates, with improved activity compared to previous variants.
PROTEIN ENGINEERING DESIGN & SELECTION
(2022)
Article
Biology
Muhammad Hermawan Widyananda, Septian Tri Wicaksono, Kurnia Rahmawati, Sapti Puspitarini, Siti Mariyah Ulfa, Yoga Dwi Jatmiko, Masruri Masruri, Nashi Widodo
Summary: This study confirms the potential of Boesenbergia rotunda as an anticancer candidate through in vitro and in silico approaches. The study identified several bioactive compounds in B. rotunda that have anticancer activity. These compounds target proteins involved in cancer progression pathways, inhibiting growth and inducing apoptosis of cancer cells.
Article
Biochemistry & Molecular Biology
Andy Pranata, Sean Yamada, Sumudu Weththasinghe, Karen Caldwell, Paul W. Zahra, Steven L. Karamatic, Michael G. Gardiner, Malcolm D. McLeod
Summary: Delta 6-Methyltestosterone has been identified as the main active compound in Jungle Warfare, a dietary supplement. It has similar structure to 17 alpha-methyltestosterone but with an extra Delta 6 double bond, leading to concerns about its potential androgenic effects and abuse in sports. In vivo metabolism studies in greyhounds revealed the presence of urinary phase I and phase II metabolites, with the major phase I metabolite identified as 16 alpha,17 beta-dihydroxy-17 alpha-methylandrosta-4,6-dien-3-one. Glucuronide conjugated metabolites were also observed but resistant to hydrolysis. This study provides a method for detecting Jungle Warfare abuse in greyhounds, useful for anti-doping laboratories.
Article
Chemistry, Multidisciplinary
Alyaa Farrah Dibha, Masruri Masruri, Arie Srihardyastutie
Summary: This research focuses on the development of degradable bioplastics using pinewood nanocellulose as a filler in PVA matrices. The study involves the isolation and characterization of cellulose and nanocellulose, and the manufacturing of degradable bioplastics using PVA, nanocellulose, and orange peel extract. The results show that the addition of orange peel extract improves the mechanical properties and degradability of the bioplastics.
INDONESIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Christopher C. J. Fitzgerald, Malcolm D. McLeod
Summary: This study reports a new stable isotope label for sulfate metabolites, which enables the synthesis of various SIL-steroid conjugates suitable for mass spectrometry detection and internal standards. The method was applied to investigate the mass spectrometry behavior of steroid bis(sulfate) compounds through collision-induced dissociation experiments.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Proceedings Paper
Chemistry, Multidisciplinary
Zulfa Durrotun Nasihin, Masruri Masruri, Warsito Warsito, Arie Srihardyastutie
2ND INTERNATIONAL CONFERENCE ON CHEMISTRY AND MATERIAL SCIENCE (IC2MS)
(2020)
Proceedings Paper
Chemistry, Multidisciplinary
Dwika Putri Pangesti, Masruri Masruri
2ND INTERNATIONAL CONFERENCE ON CHEMISTRY AND MATERIAL SCIENCE (IC2MS)
(2020)
Proceedings Paper
Chemistry, Multidisciplinary
Moh Farid Rahman, Masruri Masruri, Alyaa Farrah Dibha
2ND INTERNATIONAL CONFERENCE ON CHEMISTRY AND MATERIAL SCIENCE (IC2MS)
(2020)
Proceedings Paper
Chemistry, Multidisciplinary
Retno Indriatie, Siti Mudaliana, Febriyana Rizky Hapsari, Masruri Masruri
2ND INTERNATIONAL CONFERENCE ON CHEMISTRY AND MATERIAL SCIENCE (IC2MS)
(2020)
