Organic & Biomolecular Chemistry Blog

Uncovering a new type of phosphoramidite prodrug, Piet Herdewijn et al. at the Katholieke Universiteit Leuven (Belgium) describe the synthesis and biological evaluation of phosphoramidate d4T derivatives against HIV. Some of the newly synthesized compounds were found to act as chain terminators for HIV-1 RT, thus inhibiting HIV-1 replication.

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Synthesis and in vitro enzymatic and antiviral evaluation of phosphoramidate d4T derivatives as chain terminators Shiqiong Yang, Christophe Pannecouque, Eveline Lescrinier, Anne Giraut and Piet Herdewijn
DOI: 10.1039/C1OB06214J

While L-sugars are promising candidates in medicinal chemistry, such as L-ribose-containing nucleosides, only their D-forms naturally occur, thus prompting the need for an efficient synthetic methodology.

In this aim, Gaik-Khuan Chuah et al. at the National University of Singapore have devised a novel route to access rare L-lyxose and L-ribose in a simple 5-step procedure, leading to significantly increased yields and greener conditions as compared to previous reports.

To overcome the critical step for the oxidation of D-sugar to the corresponding D-lactone, the authors have used a heterogeneous catalyst – palladium-bismuth supported on carbon – and molecular oxygen, thus eliminating the need for bromine often used for this oxidation. The catalyst can easily be separated from the reaction mixture and reused, which enhances even further the relevance of this novel protocol.

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Reference
A heterogeneous Pd–Bi/C catalyst in the synthesis of L-lyxose and L-ribose from naturally occurring D-sugars
Ao Fan, Stephan Jaenicke and Gaik-Khuan Chuah
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06116J, Paper

In this Hot article, Adam T. Slósarczyk and Lars Baltzer from Uppsala University, Sweden, report on the conjugation of designed polypeptides to a small organic molecule as a strategy for the recognition and binding of phosphorylated proteins.

Conjugating a polypeptide to the zinc chelating ligand led to a dramatic increase in affinity and selectivity towards phosphoproteins, here caseins, however this concept for binder development is thought to be widely applicable and ‘high-affinity binders can conveniently be developed for a variety of proteins including those with posttranslational modifications for which small molecule recognition elements are available.’, report the authors.

Curious to learn more? Read the full article now, FREE to access for the next 4 weeks.

Reference
The molecular recognition of phosphorylated proteins by designed polypeptides conjugated to a small molecule that binds phosphate
Adam T. Ślósarczyk and Lars Baltzer
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06154B, Paper