Org. and Biomol. Chem.

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Design and synthesis of a macrosphelide A-biotin chimera

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7127-7135
DOI: 10.1039/C4OB01028K, PaperHwayoung Yun, Jaehoon Sim, Hongchan An, Jeeyeon Lee, Hun Seok Lee, Young Kee Shin, Seung-Mann Paek, Young-Ger Suh
The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target.
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A large dipole moment to promote gelation for 4-nitrophenylacrylonitrile derivatives with gelation-induced emission enhancement properties

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7110-7118
DOI: 10.1039/C4OB00768A, PaperPengchong Xue, Boqi Yao, Yuan Zhang, Peng Chen, Kechang Li, Baijun Liu, Ran Lu
4-Nitrophenylacrylonitrile derivatives were gelator, but analogues without nitro group were not, indicating that the electron-withdrawing nitro moiety was important for gel formation. Moreover, the organogels exhibited fluorescence enhancement.
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Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7083-7091
DOI: 10.1039/C4OB01251H, PaperOlga Lavinda, Vi Tuong Tran, K. A. Woerpel
Nucleophilic substitution reactions of five-membered ring acetals bearing fused rings reveal that subtle changes in the structure of the fused ring can exert dramatic influences on selectivity.
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Expedient synthesis of an [small alpha]-S-(1[rightward arrow]6)-linked pentaglucosyl thiol

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7119-7126
DOI: 10.1039/C4OB01094A, PaperHuali Wang, Xiangming Zhu
An [small alpha]-S-(1[rightward arrow]6)-linked pentaglucosyl thiol (1) is synthesized via the longest linear sequence of eleven steps from an [small alpha]-glucosyl thiol (7).
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Ratiometric fluorescence chemosensor based on tyrosine derivatives for monitoring mercury ions in aqueous solutions

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7100-7109
DOI: 10.1039/C4OB01044B, PaperPonnaboina Thirupathi, Ponnaboina Saritha (nee Gudelli), Keun-Hyeung Lee
Ratiometric fluorescent chemosensors 1 and 2 were synthesized based on tyrosine amino acid derivatives with a pyrene fluorophore.
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Monitoring penetratin interactions with lipid membranes and cell internalization using a new hydration-sensitive fluorescent probe

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7036-7044
DOI: 10.1039/C4OB01242A, PaperOleksandr M. Zamotaiev, Viktoriia Y. Postupalenko, Volodymyr V. Shvadchak, Vasyl G. Pivovarenko, Andrey S. Klymchenko, Yves Mely
A new hydration-sensitive fluorescent label attached to the N-terminus of a cell-penetrating peptide allows visualization of the nanoscopic environment of its internalization pathway.
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Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (+/-)-epi-indolizidine 167B and 209D

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7026-7035
DOI: 10.1039/C4OB01130A, PaperAnil K. Saikia, Kiran Indukuri, Jagadish Das
A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (+/-)-epi-indolizidine 167B and 209D.
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Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7068-7082
DOI: 10.1039/C4OB00767K, PaperLuis A. Polindara-Garcia, Alfredo Vazquez
A simple and convenient synthetic methodology to prepare nicotine derivatives is reported.
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Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7045-7058
DOI: 10.1039/C4OB01007H, PaperMario Marcia, Prabhpreet Singh, Frank Hauke, Michele Maggini, Andreas Hirsch
The synthesis, characterization and metal complexation of a new class of perylene bisimides (PBIs) as an integral part of ethylenediaminetetraacetic acid (EDTA) are reported.
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Control of reaction pathways in the photochemical reaction of a quinone with tetramethylethylene by metal binding

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7004-7017
DOI: 10.1039/C4OB00659C, PaperHiroaki Yamamoto, Kei Ohkubo, Seiji Akimoto, Shunichi Fukuzumi, Akihiko Tsuda
Supramolecular photochemical reactions of a quinone derivative, bearing an oligoether sidearm, with tetramethylethylene occur upon noncovalent complexations with metal salts.
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Evaluation of 4-substituted styrenes as functional monomers for the synthesis of theophylline-specific molecularly imprinted polymers

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,6994-7003
DOI: 10.1039/C4OB00517A, PaperHazit Zayas, Clovia I. Holdsworth, Michael C. Bowyer, Adam McCluskey
Six novel functional monomers (M1-M6) were examined for their ability to imprint theophylline (1). The best selectivity was observed with M2.
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Indole synthesis from N-allenyl-2-iodoanilines under mild conditions mediated by samarium(II) diiodide

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6812-6815
DOI: 10.1039/C4OB01164C, CommunicationHiroki Iwasaki, Kenji Suzuki, Mitsunari Yamane, Shohei Yoshida, Naoto Kojima, Minoru Ozeki, Masayuki Yamashita
A novel method for indole skeleton synthesis under mild conditions mediated by samarium(II) diiodide has been developed.
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CoPc-catalyzed selective radical arylation of anilines with arylhydrazines for synthesis of 2-aminobiaryls

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6922-6926
DOI: 10.1039/C4OB00798K, PaperTao Jiang, Sheng-Yan Chen, Guo-Yu Zhang, Run-Sheng Zeng, Jian-Ping Zou
CoPc-catalyzed selective radical arylation of anilines with arylhydrazines to afford 2-aminobiaryls in moderate to good yields is described.
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Orthogonal functionalisation of [small alpha]-helix mimetics

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6794-6799
DOI: 10.1039/C4OB00915K, CommunicationOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Anna Barnard, Kerya Long, David J. Yeo, Jennifer A. Miles, Valeria Azzarito, George M. Burslem, Panchami Prabhakaran, Thomas A. Edwards, Andrew J. Wilson
We present methodology to modify N-alkylated aromatic oligoamide [small alpha]-helix mimetics using 'click' chemistry.
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Direct intermolecular C-H arylation of unactivated arenes with aryl bromides catalysed by 2-pyridyl carbinol

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6820-6823
DOI: 10.1039/C4OB01211A, CommunicationYinuo Wu, Pui Ying Choy, Fuk Yee Kwong
A general C-H arylation of unactivated arenes by aryl/heteroaryl bromides in the presence of 2-pyridyl carbinol and potassium tert-butoxide is described.
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L-Rhamnose-containing supramolecular nanofibrils as potential immunosuppressive materials

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6816-6819
DOI: 10.1039/C4OB01362J, CommunicationFan Zhao, Balthasar A. Heesters, Isaac Chiu, Yuan Gao, Junfeng Shi, Ning Zhou, Michael C. Carroll, Bing Xu
The nanofibrils of an L-rhamnose-based hydrogelator illustrate the first example of the supramolecular assemblies of a saccharide to suppress immunity.
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New reagents for detecting free radicals and oxidative stress

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6757-6766
DOI: 10.1039/C4OB01172D, Review ArticleMina Barzegar Amiri Olia, Carl H. Schiesser, Michelle K. Taylor
This short review highlights recent progress in the development of reagents for the detection of free radicals and reactive oxygen species, a key step on the road to their understanding and ultimate control.
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Design and synthesis of potent macrocyclic HIV-1 protease inhibitors involving P1-P2 ligands

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6842-6854
DOI: 10.1039/C4OB00738G, PaperArun K. Ghosh, Gary E. Schiltz, Linah N. Rusere, Heather L. Osswald, D. Eric Walters, Masayuki Amano, Hiroaki Mitsuya
A series of potent macrocyclic HIV-1 protease inhibitors have been designed and synthesized.
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Total synthesis of putative montamine and a proposed structural reassignment

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6878-6884
DOI: 10.1039/C4OB01304B, PaperLachlan M. Blair, Elizabeth A. Colby Davie, Jonathan Sperry
The spectroscopic data for synthetic montamine does not match the proposed N,N[prime or minute]-linked structure and closely resembles a known 4,4[prime or minute]-bismoschamine natural product.
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Cross-catalytic peptide nucleic acid (PNA) replication based on templated ligation

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6901-6907
DOI: 10.1039/C4OB01158A, PaperAbhishek Singhal, Peter E. Nielsen
PNA replication via decameric template directed cross-catalytic ligation follows product inhibited kinetics yielding approximately two replication rounds.
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