Org. and Biomol. Chem.

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Updated: 6 hours 14 min ago

Maleimide as efficient nucleophilic partner in aza-Morita-Baylis-Hillman reaction: Synthesis of chiral 3-substituted-3-aminooxindoles

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00182J, PaperAkshay Kumar, Vivek Sharma, Jasneet Kaur, Naveen Kumar, Swapandeep Singh Chimni
A highly enantioselective Morita-Baylis-Hillman reaction of maleimides with isatin derived ketimines has been developed to obtain enantiomerically enriched 3-substituted-3-aminooxindoles using [small beta]-isocupreidine as an organocatalyst. Maleimide acting as a nucleophile provide...
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Synthesis and Complementary Self-association of Novel Lipophilic pi-Conjugated Nucleoside Oligomers

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00098J, PaperDavid Gonzalez-Rodriguez, Jorge Camacho-Garcia, Carlos Montoro-Garcia, Ana Lopez-Perez, Nerea Bilbao, Sonia Romero-Perez
A series of lipophilic nucleosides comprising natural and non-natural bases that are pi-conjugated to a short oligophenylene-ethynylene fragment has been synthesized. These bases comprise guanosine, isoguanosine, 2-aminoadenosine as purine heterocycles,...
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Tetraphenylethene Modified [n]Rotaxanes: Synthesis, Characterization and Aggregation-Induced Emission Behaviors

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00068H, PaperJun Yin, Guoxing Liu, Di Wu, Jinhua Liang, xie han, Shenghua Liu
A series of novel [n]rotaxanes based on tetraphenylethene (TPE) backbone were constructed by a template-directed clipping approach and their structures were well-characterized. Investigation on optical properties showed that these rotaxanes...
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Absolute Configuration of Remisporines A & B

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00082C, CommunicationRobert Thomas Williamson, Edward Sherer, James R Cheeseman
The absolute configuration of remisporine B was determined based on a comparison of experimental and calculated electronic circular dichorism (ECD) spectra. Density functional theory (DFT) was used to calculate the...
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Synthesis and photosensitivity of isoxazolin-5-one glycosides

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
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 Molecular Containers: Influence of Glycoluril Oligomer Length on their Function as Solubilizing Agents

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00184F, PaperLaura Gilberg, Ben Zhang, Peter Zavalij, Vladimir Sindelar, Lyle D. Isaacs
We present the synthesis of a series of six new glycoluril derived molecular clips and acyclic CB[n]-type molecular containers (1 - 3) that all feature SO3- solubilizing groups but differ...
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N-(1-Oxy-2-picolyl)oxalamic Acids as New Type of O,O-Ligands for the Cu-Catalyzed N-Arylation of Azoles with Aryl Halides in Water or Organic Solvent

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00045A, PaperYongbin Wang, Yu Zhang, Beibei Yang, Ao Zhang, Qizheng Yao
N-(1-Oxy-pyridin-2-ylmethyl)oxalamic acids (L3-L5) were identified as novel efficient ligands for copper-catalyzed C-N cross-coupling of azoles and aryl halides in water. The N-arylation of imidazoles, indoles and pyrazoles proceeded with moderate...
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X-ray crystallographic and kinetic investigations of 6-sulfamoyl-saccharin as a carbonic anhydrase inhibitor

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02648A, PaperVincenzo Alterio, Muhammet tanc, J Ivanova, Raivis Zalubovskis, Igor Vozny, Simona Maria Monti, Anna Di Fiore, Giuseppina De Simone, Claudiu Supuran
6-Sulfamoyl-saccharin was investigated as an inhibitor of 11 [small alpha]-carbonic anhydrase (CA, EC 4.2.1.1) isoforms of human (h) origin, hCA I-XIV, and X-ray crystallographic data were obtained for its adduct with...
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First total synthesis of the marine natural products clavulolactones II and III.

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00074B, PaperCharlotte Marie Miller, T Benneche, Marcus Tius
The first total synthesis of the marine prostanoids clavulolactones II and III is presented from an easily accessible chiral, non-racemic cyclopentenone intermediate. Key steps involve selective TBDMS deprotection, selective reduction...
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Functionalized Triazolopeptoids - a class for mitochondrial targeted delivery

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00250H, PaperDaniela Althuon, Franziska Ronicke, Daniel Furniss, Jasmin Quan, Isabelle Wellhofer, Nicole Jung, Ute Schepers, Stefan Braese
Here we introduce linear 1,4-triazolopeptoids as a novel class of cell penetrating peptidomimetics suitable as organ targeting molecular transporters of bioactive cargo. Repetitive triazole moieties with up to three submonomers...
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Strategically Designed Biomodel: Engineering C3-C4 cleavage of D-Fructose

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02666G, PaperPalwinder Singh, Arun Kumar, Sukhmeet Kaur, Amrinder Singh
Amongst a library of aldolase inspired, rationally designed compounds; the acridine derivative carrying (S)-Tyr-Gly-(S)-Lys tripeptide selectively effected C3 - C4 scissoring of D-fructose and produced D-glyceraldehyde and dihydroxyacetone.
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Efficacious redox-responsive gene delivery in serum by ferrocenylated monomeric and dimeric cationic cholesterols

6 hours 14 min ago
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02513J, PaperGururaja Vulugundam, Krishan Kumar, Paturu Kondaiah, Santanu Bhattacharya
Herein, we present the design and synthesis of new redox-active monomeric and dimeric (gemini) cationic lipids based on ferrocenylated cholesterol derivatives for gene delivery. The cationic cholesterols are shown to...
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Palladium-catalyzed regio-selective oxidative C-H bond acylation of azoxybenzenes with alcohols

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00089K, CommunicationLekai Hou, Xiangxiang Chen, Shuang Li, Suxian Cai, Yanxia Zhao, Meng Sun, Xiao-Juan Yang
A novel catalytic system for the ortho-acetyl functionalization of azoxybenzenes via a regio-selective directing-group-assisted strategy was developed.
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Frontier orbitals and transition states in the oxidation and degradation of L-ascorbic acid: a DFT study

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
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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DMSO/Tf2O-mediated cross-coupling of tryptamine with substituted aniline to access C3a-N1[prime or minute]-linked pyrroloindoline alkaloids

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
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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Bi- to tetravalent glycoclusters presenting GlcNAc/GalNAc as inhibitors: from plant agglutinins to human macrophage galactose-type lectin (CD301) and galectins

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00048C, PaperSabine Andre, Shane O'Sullivan, Christiane Koller, Paul V. Murphy, Hans-Joachim Gabius
The trimeric C-type lectin MGL is involved in activating immune defence and virus uptake, thus becoming a target for inhibitor design. A tetravalent cluster with [small alpha]-S-GalNAc proved to be effective in the nM range.
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A polystyrene-supported 9-amino(9-deoxy)epi quinine derivative for continuous flow asymmetric Michael reactions

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00325C, PaperJavier Izquierdo, Carles Ayats, Andrea H. Henseler, Miquel A. Pericas
A polystyrene (PS)-supported 9-amino(9-deoxy)epi quinine derivative catalyzes Michael reactions affording excellent levels of conversion and enantioselectivity using different nucleophiles and structurally diverse enones under continuous flow conditions.
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Stapling monomeric GCN4 peptides allows for DNA binding and enhanced cellular uptake

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
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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Design, synthesis, and kinetic analysis of potent protein N-terminal methyltransferase 1 inhibitors

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00120J, CommunicationGang Zhang, Stacie Lynn Richardson, Yunfei Mao, Rong Huang
A novel clicked bisubstrate analogue (NAM-TZ-SPKRIA) was designed and synthesized to be a potent, selective, and first NTMT1 inhibitor.
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Synthesis of 3-aminoBODIPY dyes via copper-catalyzed vicarious nucleophilic substitution of 2-halogeno derivatives

6 hours 14 min ago

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02626H, PaperJulian G. Knight, Rua B. Alnoman, Paul G. Waddell
Copper catalysed vicarious nucleophilic substitution of 2-halogeno BODIPYs with alkyl amines, anilines and an amide produces the corresponding 3-aminoBODIPY derivatives.
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