Org. and Biomol. Chem.

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Scalable synthesis of the unusual amino acid segment (ADMOA unit) of marine anti-inflammatory peptide: solomonamide A

4 May, 2015 - 09:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00481K, PaperChandrasekhar Srivari, Nerella Kavitha
The most abundantly available hexose sugar, D-Glucose has been converted to protected 4-amino(2[prime or minute]amino-4[prime or minute]-hydroxy phenyl)-3,5-dihydroxy-2-methyl-6-oxo hexanoic acid (protected ADMOA, 3), the unusual amino acid present in marine natural product solomonamide A...
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Effect of preorganization on the affinity of synthetic DNA binding motifs for nucleotide ligands

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00508F, PaperS. Vollmer, C. Richert
Triple helices with an abasic bridge between two oligopurine segments bind ligands like ATP, FAD, and cAMP with dissociation constants as low as 30 nM.
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An improved transition-metal-free synthesis of aryl alkynyl sulfides via substitution of a halide at an sp-centre

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00494B, CommunicationRoomi Mohima Chowdhury, Jonathan D. Wilden
A simple high-yielding preparation of aryl alkynyl sulfides is presented. The reaction of a chloroacetylene with a thiolate salt in the presence of an amine mediator (dimethylamine or N,N[prime or minute]-dimethylethylenediamine) yields the alkynyl sulfides in excellent yields. The alkynyl chloride is easily prepared from the parent alkyne.
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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00541H, PaperAli H. Essa, Reinner I. Lerrick, Ece Ciftci, Ross W. Harrington, Paul G. Waddell, William Clegg, Michael J. Hall
2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations.
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Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system - developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00634A, PaperJiangang Yu, Gerald Kehr, Constantin G. Daniliuc, Christoph Bannwarth, Stefan Grimme, Gerhard Erker
A convenient way to a new class of geminal Mes2PH+/B(C6F5)2H- pairs is presented.
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Simultaneous introduction of trifluoromethyl and [small lambda]6-pentafluorosulfanyl substituents using F5S-C[triple bond, length as m-dash]C-CF3 as a dienophile

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00610D, CommunicationBlazej Duda, Dieter Lentz
SF5-C[triple bond, length as m-dash]C-CF3 as a powerful dienophile in Diels-Alder reactions, provides the corresponding products in up to quantitative yields and allows the introduction of the pentafluorosulfanyl group and trifluoromethyl group at the 1,2 position.
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Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00650C, CommunicationMohammed Salah Ayoup, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan
A synthesis of amino acids carrying the all-cis tetrafluorocyclohexyl ring moiety is demonstrated and protection/deprotection elaborations are illustrated which show that this facially polarised ring motif may be incorporated into peptides.
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Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00576K, PaperSteven M. Wales, Katherine A. Hammer, Amy M. King, Andrew J. Tague, Dena Lyras, Thomas V. Riley, Paul A. Keller, Stephen G. Pyne
Designed binaphthyl-based, cationic peptidomimetic antimicrobials targeting C. difficile, incorporating a click-derived 1,2,3-triazole ester isostere at the C-terminus MICs of 4 [small mu ]g mL-1 against three human isolates of C. difficile.
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Synthetic studies toward the brasilinolides: controlled assembly of a protected C1-C38 polyol based on fragment union by complex aldol reactions

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00498E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Ian Paterson, Michael P. Housden, Christopher J. Cordier, Paul M. Burton, Friedrich A. Muhlthau, Olivier Loiseleur
A modular strategy for the synthesis of the immunosuppressant macrolide brasilinolide A was adopted based on coupling suitable northern and southern fragments.
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High solid-state luminescence in propeller-shaped AIE-active pyridine-ketoiminate-boron complexes

4 May, 2015 - 09:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00607D, PaperYanping Wu, Zhenyu Li, Qingsong Liu, Xiaoqing Wang, Hui Yan, Shuwen Gong, Zhipeng Liu, Weijiang He
Two pyridine-ketoiminate-based organoboron complexes were demonstrated to possess aggregation-induced emission, large Stokes shift and high quantum yield in the solid-state, which were rationalized through X-ray crystal analysis and electronic structure calculations.
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Resveratrol-based benzoselenophenes with an enhanced antioxidant and chain breaking capacity

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00193E, PaperDamiano Tanini, Lucia Panzella, Riccardo Amorati, Antonella Capperucci, Elio Pizzo, Alessandra Napolitano, Stefano Menichetti, Marco d'Ischia
One-pot selenenylation of resveratrol with Se(0) and SO2Cl2 leads to benzoselenophene derivatives with efficient Trolox-like antioxidant and chain breaking capacity.
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Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00460H, PaperN. Stumpp, P. Premnath, T. Schmidt, J. Ammermann, G. Drager, M. Reck, R. Jansen, M. Stiesch, I. Wagner-Dobler, A. Kirschning
Carolacton, a secondary metabolite isolated from the extracts of Sorangium cellulosum, causes membrane damage and cell death in biofilms of different oral bacteria.
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2-Azanorbornane - a versatile chiral aza-Diels-Alder cycloadduct: preparation, applications in stereoselective synthesis and biological activity

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00173K, Review ArticleElzbieta Wojaczynska, Jacek Wojaczynski, Karolina Kleniewska, Mateusz Dorsz, Tomasz K. Olszewski
The review presents the achievements in the field of preparation of chiral 2-azanorbornyl derivatives and their application in various stereoselective reactions as well as in biomimetic studies.
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Synthesis of two new enrichable and MS-cleavable cross-linkers to define protein-protein interactions by mass spectrometry

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,5030-5037
DOI: 10.1039/C5OB00488H, PaperAnthony M. Burke, Wynne Kandur, Eric J. Novitsky, Robyn M. Kaake, Clinton Yu, Athit Kao, Danielle Vellucci, Lan Huang, Scott D. Rychnovsky
The cross-linking Mass Spectrometry (XL-MS) technique extracts structural information from protein complexes without requiring highly purified samples, crystallinity, or large amounts of material.
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Influence of non-covalent preorganization on supramolecular effective molarities

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,4981-4992
DOI: 10.1039/C5OB00231A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Hongmei Sun, Cristina Navarro, Christopher A. Hunter
Formation of H-bonding interactions, which restrict the conformational mobility of a flexible linker, have no effect on chelate cooperativity in a family of porphyrin-pyridine complexes.
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Efficient approach to 2-hydroxy-2,3-dihydrofuran derivatives and its application for the synthesis of novel 4-(1H-pyrazol-4-yl)pyridazines

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,4976-4980
DOI: 10.1039/C5OB00163C, PaperJun-Rui Ma, Wen-Ming Shu, Kai-Lu Zheng, Fan Ni, Guo-Dong Yin, An-Xin Wu
A highly efficient method for the synthesis of 2-hydroxy-2,3-dihydrofuran derivatives from 1,4-enediones and phenacyl pyridinium halides via a domino reaction has been developed. At the same time, we also synthesize the novel 4-(1H-pyrazol-4-yl)pyridazine skeleton.
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Contribution of dihydrouridine in folding of the D-arm in tRNA

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,4960-4966
DOI: 10.1039/C5OB00164A, PaperN. Dyubankova, E. Sochacka, K. Kraszewska, B. Nawrot, P. Herdewijn, E. Lescrinier
NMR studies of the D-arm of tRNAiMet revealed the crucial role of dihydrouridine nucleoside in folding of the oligo.
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Novel ferrocene-based bifunctional amine-thioureas for asymmetric Michael addition of acetylacetone to nitroolefins

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,5054-5060
DOI: 10.1039/C5OB00298B, PaperXiaochen Ren, Chunyan He, Yingle Feng, Yonghai Chai, Wei Yao, Weiping Chen, Shengyong Zhang
An efficient method was developed to synthesize the ferrocene-based bifunctional amine-thioureas bearing multiple hydrogen-bonding donors. Asymmetric Michael addition of acetylacetone to nitroolefins catalyzed by these novel bifunctional catalysts affords the Michael adducts in high yield and moderate to excellent enantioselectivities.
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Synthesis of planar chiral [2.2]paracyclophane-based bisoxazoline ligands bearing no central chirality and application to Cu-catalyzed asymmetric O-H insertion reaction

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,4833-4836
DOI: 10.1039/C5OB00452G, CommunicationShinji Kitagaki, Kenta Sugisaka, Chisato Mukai
C 2-symmetric planar chiral [2.2]paracyclophane-based bisoxazoline ligands effectively control the asymmetric induction during the Cu-catalyzed O-H insertion reaction of [small alpha]-diazo esters.
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Metal-free oxysulfenylation of alkenes with 1-(arylthio)pyrrolidine-2,5-diones and alcohols

30 April, 2015 - 08:17

Org. Biomol. Chem., 2015, 13,4846-4850
DOI: 10.1039/C5OB00252D, CommunicationJipan Yu, Chang Gao, Zhixuan Song, Haijun Yang, Hua Fu
An easy and efficient metal-free approach to [small beta]-alkoxy sulfides has been developed. The protocol uses readily available 1-(arylthio)pyrrolidine-2,5-diones and alcohols as the oxysulfenylating agents, chloroform as the solvent, and no ligand, additive and exclusion of air were required.
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