Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Replacement of the CysA7-CysB7 disulfide bond with a 1,2,3-triazole linker causes unfolding in insulin glargine

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4059-4063
DOI: 10.1039/C5OB00160A, PaperGeoffrey M. Williams, Kathryn Lee, Xun Li, Garth J. S. Cooper, Margaret A. Brimble
Two analogues of insulin glargine containing a 1,4-disubstituted 1,2,3-triazole group in place of the CysA7-CysB7 disulfide bond were prepared using CuAAC click chemistry to efficiently join the peptide chains.
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Investigations into the decomposition of aminoacyl-substituted monosaccharide scaffolds from a drug discovery library

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4070-4079
DOI: 10.1039/C5OB00122F, PaperQ. Q. He, N. Wimmer, G. Verquin, W. Meutermans, V. Ferro
Decomposition of aminoacyl-substituted D-galactoside scaffolds under acidic conditions is dependent on the length of the side chain and is accelerated by the presence of a free hydroxyl group at C-6. In the latter case, evidence is provided that the reaction occurs via an N- to O-acyl transfer.
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Tetraphenylethene modified [n]rotaxanes: synthesis, characterization and aggregation-induced emission behavior

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4090-4100
DOI: 10.1039/C5OB00068H, PaperGuoxing Liu, Di Wu, Jinhua Liang, Xie Han, Sheng Hua Liu, Jun Yin
A series of novel [n]rotaxanes based on a tetraphenylethene (TPE) backbone were constructed by a template-directed clipping approach and their structures were well-characterized.
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Synthesis and photosensitivity of isoxazolin-5-one glycosides

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4025-4030
DOI: 10.1039/C5OB00244C, PaperTobias Becker, Prashant Kartikeya, Christian Paetz, Stephan H. von Reu[German sz ligature}, Wilhelm Boland
An improved synthetic protocol is described, allowing the synthesis of novel and naturally occurring isoxazolin-5-one glycosides. The photohydrolysis efficiency and pH stability of the obtained isoxazolin-5-one glycosides was studied.
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Acyclic cucurbit[n]uril-type molecular containers: influence of glycoluril oligomer length on their function as solubilizing agents

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4041-4050
DOI: 10.1039/C5OB00184F, PaperLaura Gilberg, Ben Zhang, Peter Y. Zavalij, Vladimir Sindelar, Lyle Isaacs
A series of glycoluril molecular clips and acyclic CB[n]-type receptors are tested as solubilizing agents for insoluble drugs.
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N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4101-4114
DOI: 10.1039/C5OB00045A, PaperYongbin Wang, Yu Zhang, Beibei Yang, Ao Zhang, Qizheng Yao
A new type of chelators was identified as efficient ligands for promoting Cu-catalyzed N-arylation of azoles with applicability to different solvents.
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X-ray crystallographic and kinetic investigations of 6-sulfamoyl-saccharin as a carbonic anhydrase inhibitor

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4064-4069
DOI: 10.1039/C4OB02648A, PaperV. Alterio, M. Tanc, J. Ivanova, R. Zalubovskis, I. Vozny, S. M. Monti, A. Di Fiore, G. De Simone, C. T. Supuran
Sulfamoylated saccharin binds to human carbonic anhydrase II through the SO2NH2 and not CONHSO2 moiety.
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First total synthesis of the marine natural products clavulolactones II and III

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4051-4058
DOI: 10.1039/C5OB00074B, PaperCharlotte M. Miller, Tore Benneche, Marcus A. Tius
The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate.
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Frontier orbitals and transition states in the oxidation and degradation of L-ascorbic acid: a DFT study

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4002-4015
DOI: 10.1039/C5OB00035A, PaperShinichi Yamabe, Noriko Tsuchida, Shoko Yamazaki, Shigeyoshi Sakaki
DFT calculations were carried out to investigate reaction paths of L-ascorbic acid, hydroxyl radicals and water clusters up to threonic, oxalic, xylonic and lyxonic acids.
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Reactivities of vinyl azides and their recent applications in nitrogen heterocycle synthesis

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3844-3855
DOI: 10.1039/C5OB00099H, Review ArticleBao Hu, Stephen G. DiMagno
This review categorizes the active intermediates generated from denitrogenation of vinyl azides under different reaction conditions, and highlights newly discovered transformations of vinyl azides that lead to convenient syntheses of N-heterocycles.
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DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a-N1[prime or minute]-linked pyrroloindoline alkaloids

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3863-3865
DOI: 10.1039/C5OB00190K, CommunicationMasanori Tayu, Takako Ishizaki, Kazuhiro Higuchi, Tomomi Kawasaki
The cross-coupling of tryptamine with substituted aniline to C3a-nitrogen-linked pyrroloindolines has been developed via the consecutive cyclization of tryptamine with DMSO/Tf2O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline.
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Stapling monomeric GCN4 peptides allows for DNA binding and enhanced cellular uptake

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3856-3862
DOI: 10.1039/C4OB02659D, CommunicationAbhishek Iyer, Dorien Van Lysebetten, Yara Ruiz Garcia, Benoit Louage, Bruno G. De Geest, Annemieke Madder
Facile synthesis of DNA binding stapled peptides which show enhanced cellular uptake is described considering the GCN4 transcription factor as a model protein.
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Cytotoxic scalarane sesterterpenoids from the South China Sea sponge Carteriospongia foliascens

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,4016-4024
DOI: 10.1039/C4OB02532F, PaperFei Cao, Ze-Hong Wu, Chang-Lun Shao, Sen Pang, Xiao-Yan Liang, Nicole J. de Voogd, Chang-Yun Wang
Cytotoxic scalarane sesterterpenoids from the sponge Carteriospongia foliascens collected from the South China Sea.
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Development of a flow method for the hydroboration/oxidation of olefins

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3871-3877
DOI: 10.1039/C5OB00170F, CommunicationJose A. Souto, Robert A. Stockman, Steven V. Ley
A method for the continuous preparation of alcohols by hydroboration/oxidation of olefins using flow techniques is described.
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Ligand- and Bronsted acid/base-switchable reaction pathways in gold(I)-catalyzed cycloisomerizations of allenoic acids

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3936-3949
DOI: 10.1039/C4OB02640C, PaperSachin Handa, Sri S. Subramanium, Aaron A. Ruch, Joseph M. Tanski, LeGrande M. Slaughter
Competing gold-catalyzed cycloisomerizations of [gamma]-allenoic acids are optimized through ligand and Bronsted acid/base effects, affording three distinct classes of lactones.
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Crispene E, a cis-clerodane diterpene inhibits STAT3 dimerization in breast cancer cells

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3882-3886
DOI: 10.1039/C5OB00052A, CommunicationJulia Mantaj, S. M. Abdur Rahman, Bishwajit Bokshi, Choudhury M. Hasan, Paul J. M. Jackson, Richard B. Parsons, Khondaker M. Rahman
Crispene E inhibited STAT3 dimerization in a cell-free fluorescent polarization assay and was found to have significant toxicity against STAT3-dependent MDA-MB 231 breast cancer cell line and selectively inhibited the expression of STAT3 and STAT3 target genes.
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Design and solid phase synthesis of new DOTA conjugated (+)-biotin dimers planned to develop molecular weight-tuned avidin oligomers

24 March, 2015 - 23:17

Org. Biomol. Chem., 2015, 13,3988-4001
DOI: 10.1039/C4OB02685C, PaperAlessandro Pratesi, Mauro Ginanneschi, Fabrizio Melani, Marco Chinol, Angela Carollo, Giovanni Paganelli, Marco Lumini, Mattia Bartoli, Marco Frediani, Luca Rosi, Giorgio Petrucci, Luigi Messori, Anna Maria Papini
Oligomeric architectures of avidin generated by a new class of bis-biotins.
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Peptide-DNA conjugates as tailored bivalent binders of the oncoprotein c-Jun

22 March, 2015 - 22:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00318K, PaperElena Pazos, Cecilia Portela, Cristina Penas, M. Eugenio Vazquez, Jose L. Mascarenas
A designed disrupter of the DNA complexes of oncoproteins Fos and Jun is reported.
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Visible-light-induced cleavage of 4-[small alpha]-amino acid substituted naphthalimides and its application in DNA photocleavage

22 March, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,3931-3935
DOI: 10.1039/C5OB00302D, PaperJin Zhou, Canliang Fang, Ying Liu, Yao Zhao, Nan Zhang, Xiangjun Liu, Fuyi Wang, Dihua Shangguan
4-[small alpha]-Amino acid substituted naphthalimides can be photocleaved at the C-N bond between the 4-amino and the amino acid residue under visible light irradiation, releasing a fluorophore, 4-aminonaphthalimide.
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Manganese catalysed sulfenylation of N-methyl amides with arenesulfonyl hydrazides

22 March, 2015 - 22:54

Org. Biomol. Chem., 2015, 13,3878-3881
DOI: 10.1039/C5OB00133A, CommunicationJinwei Sun, Yi Wang, Yi Pan
A convenient oxidative sulfenylation method for the formation of various sulfenyl amides has been reported.
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