Organic & Biomolecular Chemistry Blog

“Click and go”: simple and fast folic acid conjugation
Alexandre F. Trindade, Raquel F. M. Frade, Ermelinda M. S. Maçôas, Cátia Graça, Catarina A. B. Rodrigues, José M. G. Martinho and Carlos A. M. Afonso
Org. Biomol. Chem., 2014,12, 3181-3190
DOI: 10.1039/C4OB00150H 

 Cooperative hydrolysis of aryl esters on functionalized membrane surfaces and in micellar solutions
M. Poznik and B. König  
Org. Biomol. Chem., 2014,12, 3175-3180
DOI: 10.1039/C4OB00247D 

Synthesis of new anionic carbosilane dendrimers via thiol–ene chemistry and their antiviral behaviour
Marta Galán, Javier Sánchez Rodríguez, José Luis Jiménez, Miguel Relloso, Marek Maly, F. Javier de la Mata, M. A. Muñoz-Fernández and Rafael Gómez  
Org. Biomol. Chem., 2014,12, 3222-3237
DOI: 10.1039/C4OB00162A 

Strategies for the construction of tetrahydropyran rings in the synthesis of natural products
Nadiah Mad Nasir, Kristaps Ermanis and Paul A. Clarke
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00423J 

Cyclodextrin ion channels
Jonathan K. W. Chui and T. M. Fyles  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00480A 

Bis-chlorination of a hexapeptide–PCP conjugate by the halogenase involved in vancomycin biosynthesis
Patrick C. Schmartz, Katja Zerbe, Khaled Abou-Hadeed and John A. Robinson  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00474D 

An easy arylation of 2-substituted 1,2,3-triazoles
Suping Shi, Wei Liu, Ping He and Chunxiang Kuang  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00530A

Continuous flow chemistry: a discovery tool for new chemical reactivity patterns
Jan Hartwig, Jan B. Metternich, Nikzad Nikbin, Andreas Kirschning and Steven V. Ley
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00662C

Far-red and near infrared BODIPY dyes: synthesis and applications for fluorescent pH probes and bio-imaging
Yong Ni and Jishan Wu
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C3OB42554A

Phosphate esters and anhydrides – recent strategies targeting nature’s favoured modifications
Henning J. Jessen, Nisar Ahmed and Alexandre Hofer
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00478G

sp³ C–H oxidation by remote H-radical shift with oxygen- and nitrogen-radicals: a recent update
Shunsuke Chiba and Hui Chen
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00469H

A facile and convenient sequential homobimetallic catalytic approach towards ß-methylstyrenes. A one-pot Stille cross-coupling/isomerization strategy
Sebastián O. Simonetti, Enrique L. Larghi and Teodoro S. Kaufman
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00604F

An intramolecular cascade cyclization of 2-aryl indoles: efficient methods for the construction of 2,3-functionalized indolines and 3-indolinones
Arun K. Ghosh and Zhi-Hua Chen
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00511B

Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of ß-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols
Elizabeth V. Crabtree, R. Fernando Martínez, Shinpei Nakagawa, Isao Adachi, Terry D. Butters, Atsushi Kato, George W. J. Fleet and Andreas F. G. Glawar  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00097H

Preparation of functionalized heteroaromatics using an intramolecular Wittig reaction
Utpal Das, Yi-Ling Tsai and Wenwei Lin
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00464G

Practical synthesis of natural plant-growth regulator 2-azahypoxanthine, its derivatives, and biotin-labeled probes
Kazutada Ikeuchi, Ryosuke Fujii, Shimpei Sugiyama, Tomohiro Asakawa, Makoto Inai, Yoshitaka Hamashima, Jae-Hoon Choi, Tomohiro Suzuki, Hirokazu Kawagishi and Toshiyuki Kan  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00705K

A computational and experimental study of O-glycosylation. Catalysis by human UDP-GalNAc polypeptide:GalNAc transferase-T2
Hansel Gómez, Raúl Rojas, Divya Patel, Lawrence A. Tabak, José M. Lluch and Laura Masgrau
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C3OB42569J

Free to access until 25th April

Benzofuranquinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). Synthesis and biological evaluation
Catarina Carvalho, David Siegel, Martyn Inman, Rui Xiong, David Ross and Christopher J. Moody
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C3OB42258E

Free to access until 25th April

Diastereoselective Ireland–Claisen rearrangements of substituted allyl β-amino esters: applications in the asymmetric synthesis of C(5)-substituted transpentacins
Stephen G. Davies, Ai M. Fletcher, James A. Lee, Paul M. Roberts, Myriam Y. Souleymanou, James E. Thomson and Charlotte M. Zammit  
Org. Biomol. Chem., 2014, Advance Article, DOI: 10.1039/C4OB00274A

Free to access until 25th April

Biomimetic total synthesis of (±)-yezo’otogirin A
Hiu C. Lam, Kevin K. W. Kuan and Jonathan H. George  
Org. Biomol. Chem., 2014,12, 2519-2522, DOI: 10.1039/C4OB00186A

Free to access until 25th April

Anti-cooperative ligand binding and dimerisation in the glycopeptide antibiotic dalbavancin
Mu Cheng, Zyta M. Ziora, Karl A. Hansford, Mark A. Blaskovich, Mark S. Butler and Matthew A. Cooper  
Org. Biomol. Chem., 2014,12, 2568-2575, DOI: 10.1039/C3OB42428F

Free to access until 25th April

Fructose controlled ionophoric activity of a cholate–boronic acid
James R. D. Brown, Inmaculada C. Pintre and Simon J. Webb  
Org. Biomol. Chem., 2014,12, 2576-2583, DOI: 10.1039/C4OB00165F

Free to access until 25th April

Phosphodiesters serve as potentially tunable aglycones for fluoro sugar inactivators of retaining β-glycosidases
B. P. Rempel and S. G. Withers  
Org. Biomol. Chem., 2014,12, 2592-2595, DOI: 10.1039/C4OB00235K

Free to access until 25th April

Acyclic CB[n]-type molecular containers: effect of solubilizing group on their function as solubilizing excipients
Ben Zhang, Peter Y. Zavalij and Lyle Isaacs
Org. Biomol. Chem., DOI: 10.1039/C3OB42603C, Paper
Free to access until 21st April

Out-Basicity of 1,8-bis(dimethylamino)naphthalene: the experimental and theoretical challenge
Valery A. Ozeryanskii, Alexander F. Pozharskii, Alexander S. Antonov and Alexander Filarowski
Org. Biomol. Chem., DOI: 10.1039/C3OB41986J, Paper
Free to access until 21st April

Carboxy-directed asymmetric hydrogenation of α-alkyl-α-aryl terminal olefins: highly enantioselective and chemoselective access to a chiral benzylmethyl center
Shuang Yang, Shou-Fei Zhu, Na Guo, Song Song and Qi-Lin Zhou
Org. Biomol. Chem., DOI: 10.1039/C4OB00018H, Communication
Free to access until 5th April

Making Fe(BPBP)-catalyzed C–H and C=C oxidations more affordable
Vital A. Yazerski, Peter Spannring, David Gatineau, Charlotte H. M. Woerde, Sara M. Wieclawska, Martin Lutz, Henk Kleijn and Robertus J. M. Klein Gebbink
Org. Biomol. Chem., DOI: 10.1039/C3OB42249F, Paper
Free to access until 5th April

Chromane helicity rule – scope and challenges based on an ECD study of various trolox derivatives
Marcin Górecki, Agata Suszczyńska, Magdalena Woźnica, Aneta Baj, Michał Wolniak, Michał K. Cyrański, Stanisław Witkowski and Jadwiga Frelek
Org. Biomol. Chem., DOI: 10.1039/C3OB42376J, Paper
Free to access until 5th April

Reaction pathways and free energy profiles for cholinesterase-catalyzed hydrolysis of 6-monoacetylmorphine
Yan Qiao, Keli Han and Chang-Guo Zhan
Org. Biomol. Chem., DOI: 10.1039/C3OB42464B, Paper
Free to access until 10th April

Synthetic strategies toward hetidine and hetisine-type diterpenoid alkaloids
Amy M. Hamlin, Jessica K. Kisunzu and Richmond Sarpong
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42541J

Free to access until 28th March

Oxenoids in organic synthesis
Yury Minko and Ilan Marek
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42349B

Free to access until: 17th March 2014

A concise formation of N-substituted 3,4-diarylpyrroles – synthesis and cytotoxic activity
Maxim Egorov, Bernard Delpech, Geneviève Aubert, Thierry Cresteil, Maria Concepcion Garcia-Alvarez, Pascal Collin and Christian Marazano
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42309C

Free to access until: 17th March 2014

Enantioselective synthesis of α-halo-α-alkylmalonates via phase-transfer catalytic α-alkylation
Suckchang Hong, Minsik Kim, Myunggi Jung, Min Woo Ha, Myungmo Lee, Yohan Park, Mi-hyun Kim, Taek-Soo Kim, Jihoon Lee and Hyeung-geun Park
Org. Biomol. Chem., 2014, DOI: 10.1039/C3OB42107D

Free to access until: 17th March 2014

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A highly selective chemodosimeter for fast detection and intracellular imaging of Hg²⁺ ions based on a dithiocarbamate–isothiocyanate conversion in aqueous ethanol
Suman Pal, Joydev Hatai, Mousumi Samanta, Alok Shaurya and Subhajit Bandyopadhyay  
Org. Biomol. Chem., 2014,12, 1072-1078
DOI: 10.1039/C3OB42108B

Ethynylbenzenoid metabolites of Antrodia camphorata: synthesis and inhibition of TNF expression
Marco Buccini, Kathryn A. Punch, Belinda Kaskow, Gavin R. Flematti, Brian W. Skelton, Lawrence J. Abraham and Matthew J. Piggott  
Org. Biomol. Chem., 2014,12, 1100-1113
DOI: 10.1039/C3OB42333F

Free to access until 21st February 2014

Hypervalent iodine(III)-mediated cyclopropa(e)nation of alkenes/alkynes under mild conditions
Shaoxia Lin, Mengru Li, Zhiyong Dong, Fushun Liang and Jingping Zhang  
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C3OB42123F

Free to access until 21st February 2014

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Chiral amides via copper-catalysed enantioselective conjugate addition
Anne K. Schoonen, M. Ángeles Fernández-Ibáñez, Martín Fañanás-Mastral, Johannes F. Teichert and Ben L. Feringa  
Org. Biomol. Chem., 2014,12, 36-41, DOI: 10.1039/C3OB41923A 

Free to access until 16th January 2014

 Acylthioureas as anion transporters: the effect of intramolecular hydrogen bonding
Cally J. E. Haynes, Nathalie Busschaert, Isabelle L. Kirby, Julie Herniman, Mark E. Light, Neil J. Wells, Igor Marques, Vítor Félix and Philip A. Gale  
Org. Biomol. Chem., 2014,12, 62-72, DOI: 10.1039/C3OB41522H 

Free to access until 16th January 2014

Synthesis of substituted pyrenes by indirect methods
Juan M. Casas-Solvas, Joshua D. Howgego and Anthony P. Davis  
Org. Biomol. Chem., 2014,12, 212-232, DOI: 10.1039/C3OB41993B   

Free to access until 16th January 2014

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Synthesis and fluorescence characteristics of ATP-based FRET probes
Norman Hardt, Stephan M. Hacker and Andreas Marx
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41751D

Free to access until 26th December

Aromatic character and relative stability of neo-confused porphyrin tautomers and related compounds
Deyaa I. AbuSalim and Timothy D. Lash
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB42063A

Free to access until 26th December

There is no universal mechanism for the cleavage of RNA model compounds in the presence of metal ion catalysts
Heidi Korhonen, Timo Koivusalo, Suvi Toivola and Satu Mikkola
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41554F

Free to access until 26th December

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Exploring enzymatic systems that use adenosine triphosphate (ATP) can improve our understanding of various biological pathways. The production of ATP cleavage products can be monitored in vitro using radioactive ATP analogues or by the colorimetric detection of released phosphate or pyrophosphate. These methods do not allow the continuous detection of ATP turnover. Enzyme-coupled assays offer an alternative means to explore these systems, but require consideration of the effects of additional enzymes. Thus, there is a need for probes that enable the continuous study of enzymatic ATP consumption.

This HOT article describes the synthesis of ATP analogues labelled with a fluorescence donor and a fluorescence acceptor, suitable for Förster Resonance Energy Transfer. Excitation promotes energy transfer from the fluorescence donor to the fluorescence acceptor on the same molecule. Cleavage of the ATP analogue prevents energy transfer via an intramolecular pathway, resulting in a large change in fluorescence. Synthetic routes to seven new doubly labelled ATP analogues are reported and the fluorescence properties of these molecules are described using snake venom phosphodiesterase as a model enzyme.

Synthesis and fluorescence characteristics of ATP-based FRET probes
Norman Hardt, Stephan M. Hacker and Andreas Marx
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41751D

The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis
Eoin Gould, Tomas Lebl, Alexandra M. Z. Slawin, Mark Reid, Tony Davies and Andrew D. Smith
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41719K, Paper

Free to access until 2nd December

Efficient and regioselective nickel-catalyzed [2 + 2 + 2] cyclotrimerization of ynoates and related alkynes
Sanjeewa K. Rodrigo, Israel V. Powell, Michael G. Coleman, Jeanette A. Krause and Hairong Guan
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41872C, Communication

Free to access until 25th November

Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae
Jiachen Zi and Reuben J. Peters
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41885E, Communication

Free to access until 25th November

The Cope rearrangement of gem-dimethyl substituted divinylcyclopropanes
Jonathan D. Osler, William P. Unsworth and Richard J. K. Taylor
Org. Biomol. Chem., 2013, DOI: 10.1039/C3OB41617H, Paper

Free to access until 18th November

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The influenza virus is capable of crossing from animals to humans. The health threat posed by influenza jumping the species barrier has been highlighted by recent outbreaks: N5N1 ‘bird flu’ in 2003/2004, H1N1 ‘swine flu’ in 2009 and avian H7N9 earlier this year. Current methods used for the detection of influenza are time consuming and may require trained analysts and specialised equipment. There is a need for a rapid diagnostic test to discriminate between human influenza and emerging animal strains.

This HOT article describes a gold nanoparticle-based colorimetric assay for the detection of influenza. Specificity was achieved by targeting the haemagglutanin (HA) surface glycoprotein.  Human influenza binds preferentially to sialic acid α2,6 galactose sequences and avian influenza preferentially binds to sialic acid α2,3 galactose sequences. Gold nanoparticles were functionalised with trivalent α2,6-thio-linked sialic acid ligands and polyethylene glycol ligands. A solution of gold nanoparticles was used to detect HA virus surface glycoproteins and in the presence of human influenza virus a colour change was observed. The colour change was caused by the aggregation of the glycopeptide with the influenza virus and was detectable with the naked eye. Owing to the careful choice of ligands, this assay was able to discriminate between human and avian H5N1 influenza.

Glyconanoparticles for the plasmonic detection and discrimination between human and avian influenza virus
María J. Marín, Abdul Rashid, Martin Rejzek, Shirley A. Fairhurst, Stephen A. Wharton, Stephen R. Martin, John W. McCauley, Thomas Wileman, Robert A. Field and David A. Russell
Org. Biomol. Chem., 2013,11, 7101-7107
DOI: 10.1039/C3OB41703D