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https://www.readbyqxmd.com/read/28324643/unsymmetrical-iron-p-nh-p-catalysts-for-the-asymmetric-pressure-hydrogenation-of-aryl-ketones
#1
Robert Harold Morris, Samantha Alizabeth Michelle Smith, Paraskevi Olympia Lagaditis, Alan J Lough, Anne Lüpke
The reductive amination of -dialkylphosphine acetaldehydes with enantiopure -aminophosphines is a new, versatile route to unsymmetrical tridentate (pincer) ligands P-NH-P'. Four new ligands PR2CH2CH2NHCHR'CHR''PPh2 (R = iPr, Cy, R' = Ph, CH(CH3)2, R'' = Ph, H) prepared in this way are used to make the iron(II) complexes mer-FeCl2(CO)(P-NH-P') and mer-FeCl(H)(CO)(P-NH-P'). The hydride complex with the rigid ligand with R'= R''= Ph is an efficient and highly enantioselective homogeneous asymmetric pressure hydrogenation (APH) catalyst...
March 21, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28324109/sex-specific-life-course-changes-in-the-neuro-metabolic-phenotype-of-glut3-null-heterozygous-mice-ketogenic-diet-ameliorates-electroencephalographic-seizures-and-improves-sociability
#2
Yun Dai, Yuanzi Zhao, Masatoshi Tomi, Bo-Chul Shin, Shanthie Thamotharan, Andrey Mazarati, Raman Sankar, Elizabeth A Wang, Carlos Cepeda, Michael S Levine, Jingjing Zhang, Andrew Frew, Jeffry R Alger, Peter Clark, Monica Sondhi, Sudatip Kositamongkol, Leah Leibovitch, Sherin U Devaskar
We tested the hypothesis that exposure of glut3+/- mice to a ketogenic diet ameliorates autism-like features which includes aberrant behavior and electrographic seizures. We first investigated the life course sex-specific changes in basal plasma-CSF-brain metabolic profile, brain glucose transport/uptake, glucose and monocarboxylate transporter proteins, and ATP in the presence or absence of systemic insulin administration. Glut3+/- male but not female mice (5m of age) displayed reduced CSF glucose/lactate concentrations with no change in brain Glut1, Mct2, glucose uptake or ATP...
January 24, 2017: Endocrinology
https://www.readbyqxmd.com/read/28323955/rapid-onset-of-diabetic-ketoacidosis-following-sglt2-inhibition-in-a-patient-with-unrecognized-acromegaly
#3
Marino Quarella, Daniel Walser, Michael Brändle, Jean-Yves Fournier, Stefan Bilz
Context: Diabetic ketoacidosis has been described as a rare complication of acromegaly and may be observed in 1% of affected patients. The well described direct lipolytic effect of growth hormone results in increased availability of free fatty acids (FFA) for hepatic ketogenesis and is an important pathogenic event. More recently, ketoacidosis has been identified as an important complication of sodium-glucose-transport-protein 2 inhibitors (SGLT2i). Increased pancreatic glucagon secretion, impaired renal ketone body clearance and an increase in FFA concentrations secondary to decreased insulin concentrations are likely precipitating factors...
February 21, 2017: Journal of Clinical Endocrinology and Metabolism
https://www.readbyqxmd.com/read/28319305/asymmetric-grignard-synthesis-of-tertiary-alcohols-through-rational-ligand-design
#4
Bartosz Bieszczad, Declan G Gilheany
A simple, general and practical method is reported for highly enantioselective construction of tertiary alcohols through the direct addition of organomagnesium reagents to ketones. Discovered by rational ligand design based on a mechanistic hypothesis, it has an unprecedented broad scope. It utilizes a new type of chiral tridentate diamine/phenol ligand that is easily removed from the reaction mixture. It is exemplified by application to a formal asymmetric synthesis (>95:5 d.r.) of vitamin E.
March 20, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28319294/activation-of-sf6-at-platinum-complexes-formation-of-sf3-derivatives-and-their-application-in-deoxyfluorination-reactions
#5
Claudia Berg, Thomas Braun, Mike Ahrens, Philipp Wittwer, Roy Herrmann
The activation of SF6 at [Pt(PR3 )2 ] R=Cy, iPr complexes in the presence of PR3 led selectively and in an unprecedented reaction route to the generation of the SF3 complexes trans-[Pt(F)(SF3 )(PR3 )2 ]. These can also be synthesized from SF4 and the SF2 derivative trans-[Pt(F)(SF2 )(PCy3 )2 ][BF4 ] was characterized by X-ray crystallography. trans-[Pt(F)(SF3 )(PR3 )2 ] complexes are useful tools for deoxyfluorination reactions and novel fluorido complexes bearing a SOF ligand are formed. Based on these studies a process for the deoxyfluorination of ketones was developed with SF6 as fluorinating agent...
March 20, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28318943/synthesis-and-antitumor-evaluation-of-2-3-diarylbenzofuran-derivatives-on-hela-cells
#6
Guo-Xue He, Jing-Mei Yuan, Hai-Miao Zhu, Kai Wei, Ling-Yun Wang, Shi-Lin Kong, Dong-Liang Mo, Cheng-Xue Pan, Gui-Fa Su
2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22-95% yield. Sixteen targeted compounds were synthesized and characterized by (1)H NMR, (13)C NMR and HRMS. MTT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell...
March 7, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28318257/copper-i-catalyzed-enantioselective-addition-of-enynes-to-ketones
#7
Xiao-Feng Wei, Xiao-Wei Xie, Yohei Shimizu, Motomu Kanai
A copper(I)-catalyzed enantioselective addition of enynes to ketones was developed. The method allows facile construction of enantiomerically enriched tertiary alcohols using skipped enynes as stable hydrocarbon pronucleophiles. The combination of a soft copper(I)-conjugated Brønsted base catalyst with a chiral diphosphine ligand, (S,S)-Ph-BPE, enabled chemoselective deprotonation of the skipped enynes in the presence of ketones bearing intrinsically more acidic α-protons. The catalytically generated chiral allylcopper species enantio-, diastereo-, regio-, and chemoselectively reacted with ketones, thereby demonstrating excellent substrate generality with functional group tolerance...
March 21, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28318253/aminyl-radical-generation-via-tandem-norrish-type-i-photocleavage-%C3%AE-fragmentation-independent-generation-and-reactivity-of-the-2-deoxyadenosin-n6-yl-radical
#8
Liwei Zheng, Markus Griesser, Derek A Pratt, Marc M Greenberg
Formal hydrogen atom abstraction from the nitrogen-hydrogen bonds in purine nucleosides produces reactive intermediates that are important in nucleic acid oxidation. Herein we describe an approach for the independent generation of the purine radical resulting from hydrogen atom abstraction from the N6-amine of 2'-deoxyadenosine (dA•). The method involves sequential Norrish Type I photocleavage of a ketone (7b) and β-fragmentation of the initially formed alkyl radical (8b) to form dA• and acetone. The formation of dA• was followed by laser flash photolysis, which yields a transient with λmax ≈ 340 nm and a broader weaker absorption centered at ∼560 nm...
March 20, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28318235/unusual-tri-hexa-and-nonanuclear-cu-ii-cage-methylsilsesquioxanes-synthesis-structures-and-catalytic-activity-in-oxidations-with-peroxides
#9
Alexey N Bilyachenko, Alena N Kulakova, Mikhail M Levitsky, Artem A Petrov, Alexander A Korlyukov, Lidia S Shul'pina, Victor N Khrustalev, Pavel V Dorovatovskii, Anna V Vologzhanina, Ulyana S Tsareva, Igor E Golub, Ekaterina S Gulyaeva, Elena S Shubina, Georgiy B Shul'pin
Three types of unusual cagelike copper(II) methylsilsesquioxanes, namely, nona- [(MeSiO1.5)18(CuO)9] 1, hexa- [(MeSiO1.5)10(HO0.5)2(CuO)6(C12H8N2)2(MeSiO1.5)10(HO0.5)1.33(CH3COO0.5)0.67(CuO)6(C12H8N2)2] 2, [(MeSiO1.5)10(CuO)6(MeO0.5)2(C10H8N2)2] 3, and trinuclear [(MeSiO1.5)8(CuO)3(C10H8N2)2] 4, were obtained in 44%, 27%, 20%, and 16% yields, respectively. Nuclearity and structural fashion of products was controlled by the choice of solvent system and ligand, specifically assisting the assembling of cage. Structures of 1-4 were determined by single-crystal X-ray diffraction analysis...
March 20, 2017: Inorganic Chemistry
https://www.readbyqxmd.com/read/28317989/metal-free-oxidative-ring-contraction-of-benzodiazepinones-an-entry-to-quinoxalinones
#10
Hasan Mtiraoui, Kevin Renault, Morgane Sanselme, Moncef Msaddek, Pierre-Yves Renard, Cyrille Sabot
A novel and practical synthesis of 3-benzoylquinoxalin-2(1H)-ones from benzodiazepin-2-ones in two steps from commercially available starting materials is reported. The reaction was achieved in the presence of N-bromosuccinimide in DMSO which served both as a solvent and an oxidant. Significantly, the yet unknown ketone to alcohol fluorescence turn-on of benzoylquinoxalinones was unveiled through the preparation of a fluorescently labelled cholesterol conjugate.
March 20, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28317895/upregulation-of-skeletal-muscle-pgc-1%C3%AE-through-the-elevation-of-cyclic-amp-levels-by-cyanidin-3-glucoside-enhances-exercise-performance
#11
Toshiya Matsukawa, Hideko Motojima, Yuki Sato, Shinya Takahashi, Myra O Villareal, Hiroko Isoda
Regular exercise and physical training enhance physiological capacity and improve metabolic diseases. Skeletal muscles require peroxisome proliferator-activated receptor-gamma coactivator-1α (PGC-1α) in the process of their adaptation to exercise owing to PGC-1α's ability to regulate mitochondrial biogenesis, angiogenesis, and oxidative metabolism. Cyanidin-3-glucoside (Cy3G) is a natural polyphenol and a nutraceutical factor, which has several beneficial effects on human health. Here, the effect of Cy3G on exercise performance and the underlying mechanisms involved were investigated...
March 20, 2017: Scientific Reports
https://www.readbyqxmd.com/read/28317715/evaluation-of-penicillium-expansum-for-growth-patulin-accumulation-nonvolatile-compounds-and-volatile-profile-in-kiwi-juices-of-different-cultivars
#12
Yuan Wang, Tingting Shan, Yahong Yuan, Zhiwei Zhang, Chunfeng Guo, Tianli Yue
Patulin (PAT) contamination and changes of nonvolatile and volatile compounds caused by Penicillium expansum in fresh juices of 8 kiwi cultivars were investigated. Growth and PAT production of P. expansum were greater at 25°C than at 4°C. P. expansum grew in kiwi juices under pH ranging from 2.75 to 3.27 and produced 45.10-268.88μg/mL of PAT at 25°C. Decreases occurred in malic acid and soluble protein; while consumption and production simultaneously happened for reducing sugar, total soluble solid, titratable acid, citric acid, ascorbic acid and total phenolics...
August 1, 2017: Food Chemistry
https://www.readbyqxmd.com/read/28317199/enantioselective-rauhut-currier-type-1-6-conjugate-addition-of-methyl-vinyl-ketone-to-para-quinone-methides
#13
Tian-Chen Kang, Lu-Ping Wu, Qi-Wen Yu, Xin-Yan Wu
An unprecedented Rauhut-Currier-type 1,6-conjugate addition is developed. With chiral cyclohexane-based phosphine-amide catalyst 3h, the 1,6-conjugate reaction has been achieved to produce chiral diarylmethine compounds in excellent yields (91-99%) and enantioselectivities (92-98% ee).
March 20, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/28316020/%C3%AE-hydroxybutyrate-boosts-mitochondrial-and-neuronal-metabolism-but-is-not-preferred-over-glucose-under-activated-conditions
#14
Lavanya B Achanta, Benjamin D Rowlands, Donald S Thomas, Gary D Housley, Caroline D Rae
The ketone body, β-hydroxybutyrate (βOHB), is metabolised by the brain alongside the mandatory brain fuel glucose. To examine the extent and circumstances by which βOHB can supplement glucose metabolism, we studied guinea pig cortical brain slices using increasing concentrations of [U-(13)C]D-βOHB in conjunction with [1-(13)C]D-glucose under conditions of normo- and hypoglycaemia, as well as under high potassium (40 mmol/L K(+)) depolarization in normo- and hypoglycaemic conditions. The contribution of βOHB to synthesis of GABA was also probed by inhibiting the synthesis of glutamine, a GABA precursor, with methionine sulfoximine (MSO)...
March 18, 2017: Neurochemical Research
https://www.readbyqxmd.com/read/28315295/proton-nmr-metabolic-profiling-of-csf-reveals-distinct-differentiation-of-meningitis-from-negative-controls
#15
Tanushri Chatterji, Suruchi Singh, Manodeep Sen, Ajai Kumar Singh, Gaurav Raj Agarwal, Deepak Kumar Singh, Janmejai Kumar Srivastava, Alka Singh, Rajendra Nath Srivastava, Raja Roy
BACKGROUND: Cerebrospinal fluid (CSF) is an essential bio-fluid of the central nervous system (CNS), playing a vital role in the protection of CNS and performing neuronal function regulation. The chemical composition of CSF varies during onset of meningitis, neurodegenerative disorders (positive controls) and in traumatic cases (negative controls). METHODS: The study design was broadly categorized into meningitis cases, negative controls and positive controls. Further differentiation among the three groups was carried out using Principal Component Analysis (PCA) followed by supervised Partial Least Square Discriminant Analysis (PLS-DA)...
March 14, 2017: Clinica Chimica Acta; International Journal of Clinical Chemistry
https://www.readbyqxmd.com/read/28315236/detection-of-ketones-by-a-novel-technology-dipolar-proton-transfer-reaction-mass-spectrometry-dp-ptr-ms
#16
Yue Pan, Qiangling Zhang, Wenzhao Zhou, Xue Zou, Hongmei Wang, Chaoqun Huang, Chengyin Shen, Yannan Chu
Proton transfer reaction mass spectrometry (PTR-MS) has played an important role in the field of real-time monitoring of trace volatile organic compounds (VOCs) due to its advantages such as low limit of detection (LOD) and fast time response. Recently, a new technology of proton extraction reaction mass spectrometry (PER-MS) with negative ions OH(-) as the reagent ions has also been presented, which can be applied to the detection of VOCs and even inorganic compounds. In this work, we combined the functions of PTR-MS and PER-MS in one instrument, thereby developing a novel technology called dipolar proton transfer reaction mass spectrometry (DP-PTR-MS)...
March 17, 2017: Journal of the American Society for Mass Spectrometry
https://www.readbyqxmd.com/read/28306261/asymmetric-synthesis-of-the-major-metabolite-of-a-cgrp-receptor-antagonist-and-mechanism-of-epoxide-hydrogenolysis
#17
Guanglin Luo, Ling Chen, Charles M Conway, Walter Kostich, Benjamin M Johnson, Alicia Ng, John E Macor, Gene M Dubowchik
An asymmetric synthesis of the major metabolite of the CGRP recepotor antagonist BMS-846372 is presented. The variously substituted cyclohepta[b]pyridine ring system represents an under-explored ring system, and showed some unexpected chemistry. Reactivities of epoxide and ketone functional groups on cycloheptane ring were greatly controlled by a remote bulky TIPS group. The rate difference of the hydrogenolysis between two diastereomeric epoxide intermediates shed some light on the mechanism of epoxide hydrogenolysis, and further deuterium labeling studies unravelled more mechanistic details on this well known chemical transformation for the first time...
March 17, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28306251/c-o-functionalization-of-%C3%AE-oxyboronates-a-deoxygenative-gem-diborylation-and-gem-silylborylation-of-aldehydes-and-ketones
#18
Lu Wang, Tao Zhang, Wei Sun, Zeyu He, Chungu Xia, Yu Lan, Chao Liu
A deoxygenative gem-diborylation and gem-silylborylation of aldehydes and ketones is described. The key for the success of this transformation is the base-promoted C-O bond borylation or silylation of the generated α-oxyboronates. Experimental and theoretical studies exhibit that the C-O bond functionalization proceeds via an intramolecular five-membered transition-state (9-ts) boryl migration followed by a 1,2-metallate rearrangement with OBpin as a leaving group. The transformation occurs with an inversion on the carbon center...
March 17, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28304323/diabetic-ketoacidosis-complicating-pregnancy
#19
S N Bryant, C L Herrera, D B Nelson, F G Cunningham
BACKGROUND: Although diabetic ketoacidosis (DKA) in pregnancy can result in significant adverse consequences for both mother and fetus, the response to treatment, time course of recovery, and perinatal outcomes have not been well studied in pregnancy. OBJECTIVE: We examined the precipitating factors, laboratory abnormalities, treatment strategies, and clinical recovery in pregnancies complicated by DKA. STUDY DESIGN: This is a retrospective cohort study of pregnancies complicated by DKA between October 1999 and June 2015...
March 16, 2017: Journal of Neonatal-perinatal Medicine
https://www.readbyqxmd.com/read/28303514/euglycemic-ketosis-in-patients-with-type-2-diabetes-on-sglt2-inhibitor-therapy-an-emerging-problem-and-solutions-offered-by-diabetes-technology
#20
A Pfützner, D Klonoff, L Heinemann, N Ejskjaer, J Pickup
Diabetic ketoacidosis is an infrequent but life-threatening acute complication of diabetes, affecting predominantly patients with type 1 diabetes, children, and pregnant women, where ketosis is usually associated with marked hyperglycemia. Recently, an increasing number of cases have been reported of euglycemic diabetic ketoacidosis in patients with type 2 diabetes receiving sodium-glucose cotransporter 2 inhibitor treatment in routine practice. There is a minor, but not negligible diabetic ketoacidosis risk associated with this drug class, which was not seen in randomized clinical trials...
March 17, 2017: Endocrine
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