1860-39-5Relevant articles and documents
Synthesis and Inhibitory Properties of Pheromone Analogues for the Epoxide Hydrolase of the Gypsy Moth
Graham, Steven M.,Prestwich, Glenn D.
, p. 2956 - 2966 (1994)
A series of analogues of disparlure, the gypsy moth (Lymantria dispar) sex attractant, was synthesized, and the potency of these inhibitors in suppressing the metabolism of disparlure by the L. dispar epoxide hydrolase (EH) was determined.The analogues substituted at the 6-position (6-hydroxy-, 6-oxo-, and 6,6-difluorodisparlure; (+/-)-threo,cis-11, (+/-)-13, and (+/-)-17, respectively), along with 9,9-difluorodisparlure , were the most potent inhibitors (IC 50 values of 4-9 μM).Two other 9-substituted analogues, 9-hydroxydisparlure and 9-oxodisparlure , were slightly less potent (IC 50 values of 18 and 30 μM, respectively).Analogues substituted at both the 6- and 9-positions (threo,erythro-6,9-dihydroxy-, threo,threo-6,9-dihydroxy-, and 6,9-dioxodisparlure; (+/-)-threo,erythro-32, (+/-)-threo,threo-32, and (+/-)-33, respectively) were generally the least potent inhibitors (IC 50 values of 27-200 μM).On the basis of a model of the EH active site, a hypothesis is advanced to rationalize the higher potencies of the 6-substituted analogues.Pheromone metabolism plays a key role in pheromone perception, and the potential consequences of inhibition of pheromone metabolism are discussed.
A concise synthesis of (-)-(3 S,6 R)-3,6-Dihydroxy-10-methylundecanoic acid using a cross-metathesis approach
Sabitha, Gowravaram,Reddy, S. Siva Sankara,Bhaskar, Vangala,Yadav, Jhillu S.
, p. 1217 - 1222 (2010)
A new synthesis of (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid, a -hydroxy carboxylic acid, has been accomplished using a cross-metathesis reaction between two terminal olefin intermediates as the key step. Georg Thieme Verlag Stuttgart New York.
First total synthesis of (-)-(3S,6R)-3,6-dihydroxy-10-methylundecanoic acid
Zhang, Xianshu,Da, Shijun,Zhang, Chaoxin,Xie, Zhixiang,Li, Ying
, p. 507 - 509 (2006)
The first total synthesis of (3S,6R)-3,6-dihydroxy-10-methylundecanoic acid was accomplished from commercially available 1-bromo-3-methylbutane in 11 steps and 25.8% overall yield. The key steps were asymmetric allylic alkylations via allyldiisopinocampheylborane and hydroboration-oxidation.
Synthesis of Optically Active N -(4-Hydroxynon-2-enyl)pyrrolidines: Key Building Blocks in the Total Synthesis of Streptomyces coelicolor Butanolide 5 (SCB-5) and Virginiae Butanolide A (VB-A)
Donges, Jonas,Hofmann, Sandra,Walter, Johannes C.,Reichertz, Julia,Brüggemann, Moritz,Frank, Andrea,Nubbemeyer, Udo
, p. 2632 - 2642 (2021/04/27)
Starting from 5-methylhexanal and (S)-configured N -propargylprolinol ethers, coupling delivered N -(4-hydroxynon-2-ynyl)prolinol derivatives as mixtures of C4 diastereomers. Resolution of the epimers succeeded after introduction of an (R)-mandelic ester derivative and subsequent HPLC separation. Alternatively, suitable oxidation gave the corresponding alkynyl ketone. Midland reagent controlled diastereoselective reduction afforded a defined configured propargyl alcohol with high selectivity. LiAlH 4reduction and Mosher analyses of the allyl alcohols enabled structure elucidation. The suitably protected products are used as key intermediates in enantioselective Streptomyces γ-butyrolactone signaling molecule total syntheses.
Structure-Activity Relationship of para-Carborane Selective Estrogen Receptor β Agonists
Sedlák, David,Wilson, Tyler A.,Tjarks, Werner,Radomska, Hanna S.,Wang, Hongyan,Kolla, Jayaprakash Narayana,Le?nikowski, Zbigniew J.,?pi?áková, Alena,Ali, Tehane,Ishita, Keisuke,Rakotondraibe, Liva Harinantenaina,Vibhute, Sandip,Wang, Dasheng,Anzenbacher, Pavel,Bennett, Chad,Bartunek, Petr,Coss, Christopher C.
, p. 9330 - 9353 (2021/07/20)
Selective agonism of the estrogen receptor (ER) subtypes, ERα and ERβ, has historically been difficult to achieve due to the high degree of ligand-binding domain structural similarity. Multiple efforts have focused on the use of classical organic scaffold
MANUFACTURING METHOD FOR THE ALDEHYDE BY HYDROFORMYLATION REACTION
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Paragraph 0079-0081; 0083-0084; 0101, (2021/07/13)
A phosphine ligand represented by chemical formula 1. Transition metal catalyst A hydroformylation catalyst composition comprising a solvent and a solvent. Provided is a process for preparing aldehydes by hydroformylation using olefinic compounds and formaldehyde to produce aldehydes.
PROTEIN KINASE C AGONISTS
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Paragraph 0353, (2020/09/12)
The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions disclosed herein may be used for the treatment or prevention of diseases, disorders, or infections modifiable by protein kinase C (PKC) agonists, such as HIV.
A Fine Dispersed Cobalt Catalyst with Macro-Pore for Hydroformylation of 1-Hexene
Liu, Yi,Li, Zhenhao,Wang, Bin,Zhang, Yi
, p. 2252 - 2260 (2016/11/09)
Abstract: A highly dispersed cobalt catalyst for hydroformylation of 1-hexene was developed using macroporous silica (pore diameter 83.7?nm) as support. The effects of support pretreatment on the properties and catalytic activities of the obtained catalysts were investigated. The results indicated that slurry impregnation (SI) method could significantly enhance the interaction between support and cobalt precursors, leading to the formation of small cobalt particles. Moreover, this interaction would increase with the pretreating temperature or the number of hydroxyl groups in pretreating solvent. Due to the small cobalt particles and high diffusion rate of reactants and products in the macropore, the highly dispersed Co/Q-100 (PTO, SI-333) catalyst exhibited 11 times higher heptanal yield and much higher n/i ratio than the conventional Co/SiO2 (EG) catalyst which was prepared on mesoporous silica which contained similar cobalt particle size. Graphical Abstract: [Figure not available: see fulltext.]
Characterization of FabG and FabI of the Streptomyces coelicolor dissociated fatty acid synthase
Singh, Renu,Reynolds, Kevin A.
, p. 631 - 640 (2015/03/31)
Streptomyces coelicolor produces fatty acids for both primary metabolism and for biosynthesis of the secondary metabolite undecylprodiginine. The first and last reductive steps during the chain elongation cycle of fatty acid biosynthesis are catalyzed by FabG and FabI. The S. coelicolor genome sequence has one fabI gene (SCO1814) and three likely fabG genes (SCO1815, SCO1345, and SCO1846). We report the expression, purification, and characterization of the corresponding gene products. Kinetic analyses revealed that all three FabGs and FabI are capable of utilizing both straight and branched-chain β-ketoacyl-NAC and enoyl-NAC substrates, respectively. Furthermore, only SCO1345 differentiates between ACPs from both biosynthetic pathways. The data presented provide the first experimental evidence that SCO1815, SCO1346, and SCO1814 have the catalytic capability to process intermediates in both fatty acid and undecylprodiginine biosynthesis.
Screening and Engineering the Synthetic Potential of Carboxylating Reductases from Central Metabolism and Polyketide Biosynthesis
Peter, Dominik M.,Schada Von Borzyskowski, Lennart,Kiefer, Patrick,Christen, Philipp,Vorholt, Julia A.,Erb, Tobias J.
supporting information, p. 13457 - 13461 (2015/11/09)
Carboxylating enoyl-thioester reductases (ECRs) are a recently discovered class of enzymes. They catalyze the highly efficient addition of CO2 to the double bond of α,β-unsaturated CoA-thioesters and serve two biological functions. In primary metabolism of many bacteria they produce ethylmalonyl-CoA during assimilation of the central metabolite acetyl-CoA. In secondary metabolism they provide distinct α-carboxyl-acyl-thioesters to vary the backbone of numerous polyketide natural products. Different ECRs were systematically assessed with a diverse library of potential substrates. We identified three active site residues that distinguish ECRs restricted to C4 and C5-enoyl-CoAs from highly promiscuous ECRs and successfully engineered a selected ECR as proof-of-principle. This study defines the molecular basis of ECR reactivity, allowing for predicting and manipulating a key reaction in natural product diversification.
