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Convergent chemoenzymatic synthesis of a library of glycosylated analogues of pramlintide: structure-activity relationships for amylin receptor agonism

Org. and Biomol. Chem. - 57 min 4 sec ago

Org. Biomol. Chem., 2014, 12,8142-8151
DOI: 10.1039/C4OB01208A, PaperRenata Kowalczyk, Margaret A. Brimble, Yusuke Tomabechi, Antony J. Fairbanks, Madeleine Fletcher, Debbie L. Hay
The synthesis of a library of N-glycosylated pramlintide analogues to establish the SAR of amylin receptor agonism has been undertaken.
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Sialylation of lactosyl lipids in membrane microdomains by T. cruzi trans-sialidase

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01852D, PaperGavin T. Noble, Faye L. Craven, Maria Dolores Segarra-Maset, Juana Elizabeth Reyes Martinez, Robert Sardzik, Sabine L. Flitsch, Simon Webb
A synthetic perfluoroalkyl-tagged lactosyl glycolipid has been shown to form lipid microdomains in fluid phospholipid bilayers. When embedded in the membranes of phospholipid vesicles, this glycolipid was trans-sialylated by soluble...
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Protein Backbone Engineering as a Strategy to Advance Foldamers toward the Frontier of Protein-Like Tertiary Structure

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01769B, PerspectiveZachary E Reinert, William Seth Horne
A variety of non-biological structural motifs have been incorporated into the backbone of natural protein sequences. In parallel work, diverse unnatural oligomers of de novo design (termed "foldamers") have been...
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Conformationally Locked Bicyclo[4.3.0]nonane Carbanucleosides: Synthesis and Bio-evaluation

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01763C, PaperTony K. M. SHING, Anthony Wing Ho Wong, Huiyan Li, Zhifeng Liu, Paul K. S. Chan
D-Ribose has been converted into 3 novel carbobi-cyclic nucleosides bearing a bicyclo[4.3.0]nonane framework in 16-19 steps with 5-12 % overall yields involving a Wittig olefination and an intramolecular Diels-Alder reaction...
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Pyridoxine-derived bicyclic amido-, ureido-, and carbamato-pyridinols: synthesis and antiangiogenic activities

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01221F, PaperHyunji Lee, Dong-Guk Kim, Suhrid Banskota, You Kyoung Lee, Tae-gyu Nam, Jung-Ae Kim, Byeong-Seon Jeong
Preparation of a series of five- and six-membered cyclic amide-, urea-, and carbamate-fused bicyclic pyridinols and their inhibitory capacities against VEGF-induced angiogenesis are described.
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Revisiting the sparteine surrogate: development of a resolution route to the (-)-sparteine surrogate

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01694G, PaperPeter O'Brien, James D Firth, Leigh Ferris
The improved performance of the sparteine surrogate compared to sparteine in a range of applications has highlighted the need to develop an approach to the (-)-sparteine surrogate, previously inaccesible in...
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Profiling substrate specificity of two series of phenethylamine analogs at monoamine oxidase A and B

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01377H, PaperEgon Heuson, Morten Storgaard, Tri H. V. Huynh, Franck Charmantray, Thierry Gefflaut, Lennart Bunch
The membrane bound enzyme monoamine oxidase exists in two splice variants designated A and B (MAO-A and MAO-B) and are key players in the oxidative metabolism of monoamines in mammalians.
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Effects of (5[prime or minute]S)-5[prime or minute],8-cyclo-2[prime or minute]-deoxyadenosine on the base excision repair of oxidatively generated clustered DNA damage. A biochemical and theoretical study

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01089B, PaperBoleslaw T. Karwowski, Sophie Bellon, Peter O'Neill, Martine E. Lomax, Jean Cadet
Rejoining of an AP-site in ds-DNA containing the (5[prime or minute]S)-cdA in the complementary strand. Distance betwene AP-site and (5[prime or minute]S)-cdA, lanes: (1-6) -8 bases; (7-12) no (5[prime or minute]S)-cdA (control); (13-18) +8 bases.
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Highly Enantioselective and Regioselective Organocatalytic Direct Mannich Reaction of Methyl Alkyl Ketones with Cyclic Imines Benzo[e][1,2,3]oxathiazine 2,2-dioxides

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01902D, CommunicationYou-Qing Wang, Xiao-Yu Cui, Yuan-Yuan Ren, Yongna Zhang
A highly enantioselective direct Mannich reaction of methyl alkyl ketones with cyclic imines benzo[e][1,2,3]oxathiazine 2,2-dioxides, catalyzed by the combination of cinchona alkaloid derived primary amine and TFA, is disclosed. For...
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Pseudo-cyclic structures of mono- and di-azaderivatives of malondialdehydes. Synthesis and conformational disentanglement by computational analyses

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01507J, PaperMaria P. Romero Fernandez, Martin Avalos, Reyes Babiano, Pedro Cintas, Jose L. Jimenez, Mark E. Light, Juan C. Palacios
Mono- and diaza-derivatives of malondialdehydes, namely 3-alkyl(aryl)amino-2-arylacroleins and 1,5-dialkyl(aryl)-3-arylvinamidines are open-chain systems in which extended electron delocalization and pseudoaromaticity can be envisaged. A set of diversely functionalized compounds has been...
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Rapid assembly of heterocycles grafted macrocycles via tandem one-pot double 1,3-dipolar cycloaddition reaction

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01778A, PaperRaghunathan R, Purushothaman S, Prasanna R
Synthesis of triazole linked macrocycle grafted with sugarspiroheterocycles was accomplished by stereo- and regioselective tandem double 1,3-dipolar cycloaddition (1,3-DC) reaction. By this method we could construct complex chiral macrocycles in...
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Protecting-Group Directed Diastereoselective Nozaki-Hiyama-Kishi (NHK) Reaction: Total Synthesis and Biological Evaluation of Zeaenol, 7-epi-Zeaenol and its Analogues

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01811G, PaperDebendra K Mohapatra, D Sai Reddy, N Arjunreddy Mallampudi, Janardhan Gaddam, Sowjanya Polepalli, Nishant Jainb, Jhillu S. Yadav
The stereoselective total synthesis of zeaenol and 7-epi-zeaenol was achieved in a convergent manner by using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactonization reaction and...
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Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

Org. and Biomol. Chem. - 57 min 5 sec ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01655F, PaperKazuya Yamaguchi, Konomi Sakagami, Yumi Miyamoto, Xiongjie Jin, Noritaka Mizuno
Thiocyanates and trifluoromethyl sulfides are very important compounds and have classically been synthesized via multistep procedures together with formation of vast amounts of byproducts. Herein, we demonstrate oxidative nucleophilic strategy...
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Regioselective ruthenium catalysed H-D exchange using D2O as the deuterium source

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01798F, PaperLorenzo Piola, Jose A. Fernandez-Salas, Simone Manzini, Steven P. Nolan
An efficient and convenient ruthenium catalysed method for a regiospecific H/D exchange using D2O is described.
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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp2-H functionalization

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01644K, PaperPratik A. Ambasana, Dipak D. Vachhani, Marzia Galli, Jeroen Jacobs, Luc Van Meervelt, Anamik K. Shah, Erik V. Van der Eycken
Solvent steers the selectivity: Green and practical Csp2-H functionalization towards N-substituted benzo[e]- or [f]isoindolones.
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Relative stability of benziporphyrin and naphthiporphyrin tautomers and the emergence of macrocyclic diatropicity

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01659A, PaperDeyaa I. AbuSalim, Timothy D. Lash
The conformations and relative stabilities of a series of benziporphyrin and naphthiporphyrin tautomers were calculated and the diatropic properties of each of these species were assessed. The results were in good agreement with experimental observations and allow favorable delocalization pathways to be identified.
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Selective chromo-fluorogenic detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) with a unique probe based on a boron dipyrromethene (BODIPY) dye

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01299B, PaperAndrea Barba-Bon, Ana M. Costero, Salvador Gil, Ramon Martinez-Manez, Felix Sancenon
A new naked eye colorimetric BODIPY probe able to discriminate DCNP and DFP nerve agent mimics with good LODs.
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Preparation of indium nitronates and their Henry reactions

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01468E, CommunicationRaquel G. Soengas, Rita Acurcio, Artur M. S. Silva
Indium nitronates were readily prepared from commercially available nitroalkanes by transmetallation of the corresponding lithium nitronates with indium salts. The Henry reaction of this nitronates with aldehydes afforded [small beta]-nitroalkanols in moderate to high yields and excellent stereoselectivity (when using chiral aldehydes).
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A metal-free one-pot cascade synthesis of highly functionalized biaryl-2-carbaldehydes

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01829J, CommunicationChandrasekhar Challa, Jamsheena Vellekkatt, Jaice Ravindran, Ravi S. Lankalapalli
A metal-free one-pot cascade annulation of acyclic substrates dienaminodioate, cinnamaldehydes and allyl amine was achieved for the synthesis of polyfunctional biaryl-2-carbaldehydes.
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Cross-strand histidine-aromatic interactions enhance acyl-transfer rates in beta-hairpin peptide catalysts

Org. and Biomol. Chem. - 57 min 5 sec ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01754D, PaperM. Matsumoto, S. J. Lee, M. R. Gagne, M. L. Waters
A His-aryl interaction in a beta-hairpin catalyst provides rate enhancements of up to 18 000 for acyl transfer catalysis.
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