Royal Society of Chemistry

A computational study of the activation of allenoates by Lewis bases and the reactivity of intermediate adducts

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7297-7309
DOI: 10.1039/C4OB01177E, PaperGou-Tao Huang, Timm Lankau, Chin-Hui Yu
Several chemical properties of Lewis base-allenoate adducts (LB[middle dot]allenoate), such as solvent effect, basicity, nucleophilicity and cycloaddition, are studied to provide a detailed foundation for the analysis of LB-catalyzed reactions of allenoates.
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Next generation maleimides enable the controlled assembly of antibody-drug conjugates via native disulfide bond bridging

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7261-7269
DOI: 10.1039/C4OB01550A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Felix F. Schumacher, Joao P. M. Nunes, Antoine Maruani, Vijay Chudasama, Mark E. B. Smith, Kerry A. Chester, James R. Baker, Stephen Caddick
Highly homogeneous ADCs are generated by the efficient bridging of interchain disulfide bonds in trastuzumab, using next generation maleimides.
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A hydrazide-anchored dendron scaffold for chemoselective ligation strategies

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7290-7296
DOI: 10.1039/C4OB00870G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Liz O'Donovan, Paul A. De Bank
We report the design and synthesis of a dendron scaffold, enabling the chemoselective decoration of target molecules with multiple copies of functional species, such as peptides, via a hydrazone bond.
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Iridium-catalyzed C-H borylation of pyridines

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7318-7327
DOI: 10.1039/C4OB01565G, PaperScott A. Sadler, Hazmi Tajuddin, Ibraheem A. I. Mkhalid, Andrei S. Batsanov, David Albesa-Jove, Man Sing Cheung, Aoife C. Maxwell, Lena Shukla, Bryan Roberts, David C. Blakemore, Zhenyang Lin, Todd B. Marder, Patrick G. Steel
Iridium-catalysed C-H borylation is an efficient method for the preparation of pyridyl and related azinyl boronate esters.
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Investigation of transannular cycloaddition reactions involving furanoxonium ions using DFT calculations. Implications for the origin of plumarellide and rameswaralide and related polycyclic metabolites isolated from corals

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7270-7278
DOI: 10.1039/C4OB00734D, PaperB. Lygo, M. J. Palframan, G. Pattenden
DFT calculations probing potential cycloaddition pathways leading to the polycyclic ring systems found in the coral secondary metabolites plumarellide, mandapamate and rameswaralide are described.
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Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one ([small beta]-lactam), involving a cascade sequence of reactions as a key step

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7389-7396
DOI: 10.1039/C4OB00948G, PaperDipak Kumar Tiwari, Kishor Chandra Bharadwaj, Vedavati G. Puranik, Dharmendra Kumar Tiwari
A divergent, short, and novel total synthesis of 1,6,8a-tri-epi-castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed.
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Stereoselective synthesis of C-fused pyranoindoles, pyranobenzofurans and pyranobenzothiophene scaffolds using oxa-Pictet-Spengler type reaction of vinylogous carbonates

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7397-7409
DOI: 10.1039/C4OB01387E, PaperSantosh J. Gharpure, V. Prasath
C-fused pyranoheterocycles can be assembled in a highly diastereoselective manner using an intramolecular oxa-Pictet-Spengler type reaction of vinylogous carbonates.
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Linear versus branched poly-lysine/arginine as polarity enhancer tags

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7194-7196
DOI: 10.1039/C4OB01354A, CommunicationMarta Paradis-Bas, Maria Albert-Soriano, Judit Tulla-Puche, Fernando Albericio
The design and synthesis of Lys- and Arg-containing peptides as solubilizing tags were studied to evaluate their influence on polarity.
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A neighboring group participation strategy: direct and highly diastereoselective synthesis of 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7381-7388
DOI: 10.1039/C4OB00642A, PaperXiaofeng Ma, Qin Tang, Jun Ke, Jichao Zhang, Xinglong Yang, Xudong Shen, Huawu Shao
A highly diastereoselective synthesis method for 2-substituted and 2,2-bisubstituted perhydrofuro[2,3-b]pyran derivatives from 2-C-branched sugars via a neighboring group participation strategy was developed.
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Cooperative hybridization of [gamma]PNA miniprobes to a repeating sequence motif and application to telomere analysis

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7345-7354
DOI: 10.1039/C4OB00953C, PaperHa H. Pham, Connor T. Murphy, Gopalsamy Sureshkumar, Danith H. Ly, Patricia L. Opresko, Bruce A. Armitage
High affinity [gamma]PNA oligomers hybridize cooperatively on telomeric DNA and provide bright fluorescent signals.
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First total synthesis of antihypertensive natural products S-(+)-XJP and R-(-)-XJP

Org. and Biomol. Chem. - 9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7338-7344
DOI: 10.1039/C4OB01470G, PaperChaolei Wang, Guoxiang Wei, Xue Yang, Hequan Yao, Jieyun Jiang, Jie Liu, Mingqin Shen, Xiaoming Wu, Jinyi Xu
The first total synthesis of S-(+)-XJP and R-(-)-XJP has been achieved via intramolecular Heck reaction. A latent functionality strategy was implemented to circumvent the racemization in this endeavor.
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The biosafety of lanthanide upconversion nanomaterials

Chem. Soc. Rev. - 9 September, 2014 - 22:17

Chem. Soc. Rev., 2015, Advance Article
DOI: 10.1039/C4CS00175C, Review ArticleYun Sun, Wei Feng, Pengyuan Yang, Chunhui Huang, Fuyou Li
The association between the chemo-physical properties of UCNPs and their biodistribution, excretion, and toxic effects is presented in this review.
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Solid phase chemical ligation employing a rink amide linker for the synthesis of histone H2B protein

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC06499B, CommunicationMuhammad Jbara, Mallikanti Seenaiah, Ashraf Brik
A solid phase chemical ligation strategy employing native chemical ligation and a Rink-amide linker for protein synthesis.
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Formal synthesis of kingianin A based upon a novel electrochemically-induced radical cation Diels-Alder reaction

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05906A, CommunicationJonathan C. Moore, E. Stephen Davies, Darren A. Walsh, Pallavi Sharma, John E. Moses
The application of electrochemical reactions in natural product synthesis has burgeoned in recent years. We herein report a formal synthesis of the complex and dimeric natural product kingianin A, which employs an electrochemically-mediated radical cation Diels-Alder cycloaddition as the key step.
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Dinuclear osmium(II) probes for high-resolution visualisation of cellular DNA structure using electron microscopy

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05547K, CommunicationAshley Wragg, Martin R. Gill, Christopher J. Hill, Xiaodi Su, Anthony J. H. M. Meijer, Carl Smythe, Jim A. Thomas
Dinuclear osmium(II) complexes are excellent easy-to-handle probes for transmission electron microscopy, facilitating high-resolution intracellular imaging of sub-nuclear structures.
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Luminescent terbium-containing metal-organic framework films: new approaches for the electrochemical synthesis and application as detectors for explosives

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05742B, CommunicationNicolo Campagnol, Ernesto Rezende Souza, Dirk E. De Vos, Koen Binnemans, Jan Fransaer
The flexibility of the electrochemical synthesis of MOFs is illustrated by the preparation of well-adhering layers of luminescent MOFs on electrically conductive solid substrates.
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Metal coordination, and metal-ligand redox non-innocence, modulates allosteric C-N bond homolysis in an N-benzyl tetrazine

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC06235C, CommunicationCooper W. Johnston, Travis R. Schwantje, Michael J. Ferguson, Robert McDonald, Robin G. Hicks
Coordination of a ruthenium fragment to an N-benzyl tetrazine ligand reduces the (already weak) C-N bond strength by 16 kcal mol-1.
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An NIR-responsive and sugar-targeted polypeptide composite nanomedicine for intracellular cancer therapy

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05983B, CommunicationGang Liu, Linzhu Zhou, Yue Su, Chang-Ming Dong
The UCNP-loaded polypeptide composite nanoparticles that present fast NIR-sensitivity and tunable sugar-targeting properties are fabricated, opening a new avenue for on-demand and targeted cancer therapy.
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Enantioselective iodolactonization of allenoic acids

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC05414H, CommunicationKenichi Murai, Nozomi Shimizu, Hiromichi Fujioka
An enantioselective iodolactonization reaction of allenoic acids has been developed using a trisimidazoline catalyst and I2.
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Selective phosphanyl complex trapping using TEMPO. Synthesis and reactivity of P-functional P-nitroxyl phosphane complexes

Chem. Commun. - 9 September, 2014 - 03:17

Chem. Commun., 2014, Advance Article
DOI: 10.1039/C4CC06084A, CommunicationVitaly Nesterov, Zheng-Wang Qu, Gregor Schnakenburg, Stefan Grimme, Rainer Streubel
From phosphanyl to phosphanoxyl complexes: in situ reactions of phosphanyl complexes with TEMPO led to corresponding P-nitroxyl phosphane complexes, which thermally form transient phosphanoxyl complexes, the transition-metal stabilized P-analogues of nitroxyl radicals.
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