Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Modular synthesis of bis- and tris-1,2,3-triazoles by permutable sequential azide-aryne and azide-alkyne cycloadditions

18 September, 2014 - 00:17

Org. Biomol. Chem., 2014, 12,7489-7493
DOI: 10.1039/C4OB01654H, CommunicationSuguru Yoshida, Takako Nonaka, Takamoto Morita, Takamitsu Hosoya
A new method for aryne generation enabled facile synthesis of diverse bis- and tris-1,2,3-triazoles.
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Total synthesis and biological studies of cryptocin and derivatives of equisetin and fusarisetin A

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7591-7597
DOI: 10.1039/C4OB01149J, PaperLili Kong, Mingjin Rao, Jinjie Ou, Jun Yin, Weiqiang Lu, Mingyao Liu, Xiufeng Pang, Shuanhu Gao
Total synthesis of cryptocin, derivatives of equisetin and fusarisetin A were achieved based on the biosynthetic hypothesis. The biological studies of their inhibitory effects on breast cancer cells (MDA-MB-231) survival and metastasis were further investigated.
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Understanding the polar mechanism of the ene reaction. A DFT study

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7581-7590
DOI: 10.1039/C4OB01279H, PaperLuis R. Domingo, Maria J. Aurell, Patricia Perez
A good correlation between the activation energy and global electron density transfer at the transition structure of ene reactions has been found. The proposed polar mechanism can be easily predicted analysing the electrophilicity/nucleophilicity indices of the reagents.
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Modulation of DNA-polyamide interaction by [small beta]-alanine substitutions: a study of positional effects on binding affinity, kinetics and thermodynamics

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7523-7536
DOI: 10.1039/C4OB01456A, PaperShuo Wang, Karl Aston, Kevin J. Koeller, G. Davis Harris, Nigam P. Rath, James K. Bashkin, W. David Wilson
The substitution of an internal pyrrole with a [small beta] motif has large and diverse effects on hairpin polyamide-DNA binding affinity, kinetics and binding orientation.
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Synthesis of aromatic 13C/2H-[small alpha]-ketoacid precursors to be used in selective phenylalanine and tyrosine protein labelling

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7551-7560
DOI: 10.1039/C4OB01129E, PaperR. J. Lichtenecker
A synthetic concept to access various 13C/2H patterns of phenylalanine and tyrosine precursors for cell-based protein overexpression systems is presented. The target compounds feature isolated 13C-1H spin systems to be used in NMR probing of protein structure and dynamics.
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Nickel-catalyzed substitution reactions of propargyl halides with organotitanium reagents

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7634-7642
DOI: 10.1039/C4OB00677A, PaperQing-Han Li, Jung-Wei Liao, Yi-Ling Huang, Ruei-Tang Chiang, Han-Mou Gau
A simple and mild catalytic coupling reaction of propargyl halides with organotitanium reagents is reported.
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Approaches to the total synthesis of chaetochalasin A

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7537-7550
DOI: 10.1039/C4OB01308E, PaperEric J. Thomas, Mark Willis
Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels-Alder reactions.
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A theoretical study on the mechanisms of the reactions between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7503-7514
DOI: 10.1039/C4OB01015A, PaperYang Wang, Donghui Wei, Wenjing Zhang, Yanyan Wang, Yanyan Zhu, Yu Jia, Mingsheng Tang
The reaction mechanisms between 1,3-dialkynes and ammonia derivatives for the formation of five-membered N-heterocycles have been investigated using the DFT method.
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RANEY[registered sign] cobalt - an underutilised reagent for the selective cleavage of C-X and N-O bonds

15 September, 2014 - 23:54

Org. Biomol. Chem., 2014, 12,7433-7444
DOI: 10.1039/C4OB00917G, Review ArticleMartin G. Banwell, Matthew T. Jones, Tristan A. Reekie, Brett D. Schwartz, Shen H. Tan, Lorenzo V. White
The first comprehensive survey of the application of the catalyst RANEY[registered sign] cobalt in chemical synthesis is presented. Its capacity to effect chemoselective reductive cyclisation reactions under mild conditions is highlighted.
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Correction: Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

9 September, 2014 - 22:17
Org. Biomol. Chem., 2014, 12,7410-7410
DOI: 10.1039/C4OB90119C, CorrectionSilvia Bezer, Masaomi Matsumoto, Michael W. Lodewyk, Stephen J. Lee, Dean J. Tantillo, Michel R. Gagne, Marcey L. Waters
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Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes

9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7366-7374
DOI: 10.1039/C4OB01095G, PaperSandip A. Shelke, Gunnar B. Sandholt, Snorri Th. Sigurdsson
Of ten new pyrimidine-derived nitroxide spin labels, an N1-ethylamino triazole-linked uracil derivative binds fully to both DNA and RNA duplexes containing an abasic site, as determined by CW-EPR.
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Selective transamidation of 3-oxo-N-acyl homoserine lactones by hydrazine derivatives

9 September, 2014 - 22:17

Org. Biomol. Chem., 2014, 12,7197-7200
DOI: 10.1039/C4OB01156B, CommunicationMichael A. Bertucci, Stephen J. Lee, Michel R. Gagne
Hydrazine derivatives are employed for selective amide cleavage of 3-oxo-N-acyl homoserine lactones under physiologically relevant conditions.
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A computational study of the activation of allenoates by Lewis bases and the reactivity of intermediate adducts

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

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

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

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

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

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

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

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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