Org. and Biomol. Chem.

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A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02147A, PaperShuo Xing, James L. Gleason
Glycal etherification followed by azidonitration/reduction solves a difficult SN2 step in the synthesis of N-glycolyl muramyl dipeptide.
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Aryl-bis-(scorpiand)-aza receptors differentiate between nucleotide monophosphates by a combination of aromatic, hydrogen bond and electrostatic interactions

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02084G, PaperJorge Gonzalez-Garcia, Sanja Tomic, Alberto Lopera, Lluis Guijarro, Ivo Piantanida, Enrique Garcia-Espana
Bis-scorpiands bind nucleotides in water with 10-100 [small mu ]M affinity, with selectivity: at pH 7 pyridine-scorpiand toward CMP; at pH 5 phenanthroline-scorpiand toward AMP.
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Domino reaction involving the Bestmann-Ohira reagent and [small alpha],[small beta]-unsaturated aldehydes: efficient synthesis of functionalized pyrazoles

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02365J, PaperShakir Ahamad, Ashis Kumar Gupta, Ruchir Kant, Kishor Mohanan
A mild, efficient and rapid domino reaction involving the Bestmann-Ohira reagent (BOR) and [small alpha],[small beta]-unsaturated aldehydes has been developed for the synthesis of densely functionalized vinylpyrazoles.
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A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: design, synthesis, and biological evaluation

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB01605J, PaperGaofei Wei, Weijing Luan, Shuai Wang, Shanshan Cui, Fengran Li, Yongxiang Liu, Yang Liu, Maosheng Cheng
A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition reaction.
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Accelerated Fmoc solid-phase synthesis of peptides with aggregation-disrupting backbones

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02260B, PaperYi-Chao Huang, Chao-Jian Guan, Xiang-Long Tan, Chen-Chen Chen, Qing-Xiang Guo, Yi-Ming Li
In this work, we describe an accelerated solid-phase synthetic protocol for ordinary or difficult peptides involving air-bath heating and amide protection.
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Bioorthogonal labelling of 3-nitrotyrosine in peptides and proteins through diazotisation mediated azidation

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,374-378
DOI: 10.1039/C4OB02133A, CommunicationJohn Y. Ng, Jason W. H. Wong
A bioorthogonal method of transforming 3-nitrotyrosine to 3-azidotyrosine is described, providing new opportunities to study 3-nitrotyrosine in biological samples.
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Anion binding by biotin[6]uril in water

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,369-373
DOI: 10.1039/C4OB02211D, CommunicationMicke Lisbjerg, Bjarne E. Nielsen, Birgitte O. Milhoj, Stephan P. A. Sauer, Michael Pittelkow
We show that the newly discovered 6 + 6 biotin-formaldehyde macrocycle Biotin[6]uril binds a variety of anionic guest molecules in water. We discuss how and why the anions are bound based on data obtained using NMR spectroscopy, mass spectrometry, isothermal titrations calorimetry (ITC), computational calculations and single crystal X-ray crystallography.
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Cucurbituril-based supramolecular engineered nanostructured materials

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,330-347
DOI: 10.1039/C4OB02065K, Review ArticleSinem Gurbuz, Muazzam Idris, Donus Tuncel
Nanostructured materials, including nanoparticles, nanocomposites, vesicles, and rods, have been prepared by taking advantage of the interesting features of cucurbituril homologues.
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The direct electrophilic cyanation of [small beta]-keto esters and amides with cyano benziodoxole

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,365-368
DOI: 10.1039/C4OB02032D, CommunicationYao-Feng Wang, Jiashen Qiu, Dejie Kong, Yongtao Gao, Feipeng Lu, Pran Gopal Karmaker, Fu-Xue Chen
Electrophilic cyanating agent C1 accomplishes the direct cyanation of [small beta]-keto esters and amides without any catalyst and base.
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Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C-H of acetonitrile and the sp2 C-H of the phenyl group

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,361-364
DOI: 10.1039/C4OB02172J, CommunicationChangduo Pan, Honglin Zhang, Chengjian Zhu
Radical cyanomethylation/arylation of arylacrylamides to access oxindoles with acetonitrile as a radical precursor is described, involving dual C-H bond functionalization.
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Rhodium(II)-catalyzed intramolecular formal [4 + 3] cycloadditions of dienyltriazoles: rapid access to fused 2,5-dihydroazepines

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,612-619
DOI: 10.1039/C4OB01910E, PaperYu Tian, Yuanhao Wang, Hai Shang, Xudong Xu, Yefeng Tang
Rh(II)-catalyzed intramolecular formal [4 + 3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines.
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A highly efficient and eco-friendly method for the synthesis of 1,3-indandione ring-fused 3-oxindoles bearing two contiguous quaternary stereocenters via an aldol reaction in aqueous media

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,601-611
DOI: 10.1039/C4OB02103G, PaperXiong-Li Liu, Bo-Wen Pan, Wen-Hui Zhang, Chao Yang, Jun Yang, Yang Shi, Ting-Ting Feng, Ying Zhou, Wei-Cheng Yuan
The synthesis and antitumor activity evaluation of 1,3-indandione ring-fused 3-oxindoles.
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Structural insight into the aggregation of L-prolyl dipeptides and its effect on organocatalytic performance

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,592-600
DOI: 10.1039/C4OB02003K, PaperCristina Berdugo, Beatriu Escuder, Juan F. Miravet
NMR and organocatalytic studies of four dipeptides derived from L-proline are described.
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Novel synthesis of 5-methyl-5,10-dihydroindolo[3,2-b]indoles by Pd-catalyzed C-C and two-fold C-N coupling reactions

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,583-591
DOI: 10.1039/C4OB01723D, PaperTran Quang Hung, Soren Hancker, Alexander Villinger, Stefan Lochbrunner, Tuan Thanh Dang, Aleksej Friedrich, Wolfgang Breitsprecher, Peter Langer
A series of 5,10-dihydroindolo[3,2-b]indoles was successfully prepared by an efficient two-step strategy.
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Artificial metalloenzymes for the diastereoselective reduction of NAD+ to NAD2H

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,357-360
DOI: 10.1039/C4OB02071E, CommunicationTommaso Quinto, Daniel Haussinger, Valentin Kohler, Thomas R. Ward
Stereoselectively labelled isotopomers of NAD(P)H are highly relevant for mechanistic studies of enzymes which utilize them as redox equivalents.
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L-Valine derived chiral N-sulfinamides as effective organocatalysts for the asymmetric hydrosilylation of N-alkyl and N-aryl protected ketimines

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,577-582
DOI: 10.1039/C4OB01257G, PaperChao Wang, Xinjun Wu, Li Zhou, Jian Sun
L-Valine derived N-sulfinamides have been developed as efficient enantioselective Lewis basic organocatalysts for the asymmetric reduction of N-aryl and N-alkyl ketimines with trichlorosilane.
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Pd(II)-catalyzed C-H arylation of aryl and benzyl Weinreb amides

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,353-356
DOI: 10.1039/C4OB02039A, CommunicationYan Wang, Kai Zhou, Quan Lan, Xi-Sheng Wang
The first example of palladium-catalyzed ortho-C-H arylation of aryl and benzyl Weinreb amides was developed, in which HOTf was used as a key promoter.
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Naphthalene diimides as red fluorescent pH sensors for functional cell imaging

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,570-576
DOI: 10.1039/C4OB02054E, PaperFilippo Doria, Marco Folini, Vincenzo Grande, Graziella Cimino-Reale, Nadia Zaffaroni, Mauro Freccero
Water-soluble naphthalene diimides have been designed and synthesized as cell permeable pH "turned-on" fluorescent sensors for cellular applications.
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Synthesis and evaluation of protein arginine N-methyltransferase inhibitors designed to simultaneously occupy both substrate binding sites

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,549-560
DOI: 10.1039/C4OB01734J, PaperMatthijs van Haren, Linda Quarles van Ufford, Ed E. Moret, Nathaniel I. Martin
PRMT inhibitors designed to simultaneously occupy both substrate binding sites display potent activity and surprising selectivity.
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Late-stage diversification of biologically active pyridazinones via a direct C-H functionalization strategy

15 December, 2014 - 22:17

Org. Biomol. Chem., 2015, 13,539-548
DOI: 10.1039/C4OB02061H, PaperWei Li, Zhoulong Fan, Kaijun Geng, Youjun Xu, Ao Zhang
Divergent ortho-selective C-H functionalization was successfully established using a pyridazinone moiety as an internal directing group.
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