Organic & Biomolecular Chemistry Blog

In this HOT OBC paper from the ‘Nucleic acids: new life, new materials’ web collection, short and high-yielding syntheses for the nucleobases preQ1 base, Q base, and (ent)-Q base are described based on cheap and readily available starting compounds. For the latter two bases, Hans-Dieter Gerber and Gerhard Klebe use preQ1 as a central synthon and nucleophilic substitution reactions with appropriately decorated halocyclopentenyl synthons to produce the desired bases.

For the detailed discussion and reaction analysis download the paper, it is free to do so for 4 weeks!

Concise and efficient syntheses of preQ1 base, Q base, and (ent)-Q base
Hans-Dieter Gerber and Gerhard Klebe
DOI: 10.1039/C2OB26387D

Liked that? Then why not have a look at the rest of the ‘Nucleic acids: new life, new materials’ web collection.

In this HOT paper Michael J. Porter and colleagues at University College London report the synthesis of the core structure of tagetitoxin using a novel photochemical 1,2-Stevens rearrangement. The method presented by Porter et al. uses the carbene-mediated ring expansion of a bicyclic monothioacetal, through the intermediacy of a sulfonium ylide.

To see all the experimental and mechanistic details download the paper today. It will be free to access for 4 weeks!

Inter- and intramolecular reactions of 1-deoxy-1-thio-1,6-anhydrosugars with α-diazoesters: synthesis of the tagetitoxin core by photochemical ylide rearrangement
Anne J. Price Mortimer, Julien R. H. Plet, Oluwafunsho A. Obasanjo, Nikolas Kaltsoyannis and Michael J. Porter
DOI: 10.1039/C2OB26308D

Mark von Itzstein and co-workers have synthesised a series of novel C3 C-alkylated Neu5Ac2en derivatives, which by virtue of the substituent extending from C3 are probes of 150-loop flexibility in influenza virus sialidases.

Currently there is speculation as to what factors determine or affect loop flexibility in influenza A virus sialidases. The compounds described by Mark von Itzstein et al. in this HOT paper provide a way to probe sialidases for this flexibility and should help to elucidate the generality of 150-loop flexibility across all influenza virus sialidases, the factors that affect loop flexibility, and potentially the functional roles this flexibility may play.

This article is free to download for 4 weeks so find out more by reading the paper now.

Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility
Santosh Rudrawar, Philip S. Kerry, Marie-Anne Rameix-Welti, Andrea Maggioni, Jeffrey C. Dyason, Faith J. Rose, Sylvie van der Werf, Robin J. Thomson, Nadia Naffakh, Rupert J. M. Russell and Mark von Itzstein
DOI: 10.1039/C2OB25627D

In this HOT Communication Patrick J. Hrdlicka and colleagues at University of Idaho study the hybridization properties of oligonucleotides, which are modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridine monomers featuring three differentially sized aromatic moieties at the 1-position of the triazole ring.

These modified oligonucleotides modified with consecutive show a strong thermal affinity and binding specificity toward RNA targets, due to the formation of stabilizing chromophore arrays in the major groove.

This Communication can be downloaded for free for 4 weeks.

This work is also part of the OBC collection on ‘Nucleic acids: new life, new materials‘, so for related articles have a browse through the collection.

Synthesis and hybridization properties of oligonucleotides modified with 5-(1-aryl-1,2,3-triazol-4-yl)-2′-deoxyuridines
Mamta Kaura, Pawan Kumar and Patrick J. Hrdlicka
DOI: 10.1039/C2OB26717A

In this HOT Communication Adam R. Urbach and colleagues, Trinity University, present a convenient approach for the quantitative removal of the synthetic host cucurbit[8]uril from aqueous mixtures using a sepharose resin coated in memantine groups to selectively isolate cucurbit[8]uril in the presence of competing hosts and guests. The “cucurbit[8]uril sponge” can separate cucurbit[8]uril from cucurbit[6]uril and reverse the cucurbit[8]uril-mediated dimerization of peptides.

This communication is free to access for the next 4 weeks!

A cucurbit[8]uril sponge
Vijayakumar Ramalingam, Sharon K. Kwee, Lisa M. Ryno and Adam R. Urbach
DOI: 10.1039/C2OB26774H