Glycol nucleic acid (GNA) has an acyclic backbone of propylene glycol nucleosides that are connected by phosphodiester bonds. This paper characterizes the duplex-formation properties of this simplified nucleic acid. Although single and multiple GNA nucleotides are highly destabilizing if incorporated into DNA duplexes, the two enantiomeric oligomers (S)-GNA and (R)-GNA form antiparallel homoduplexes that are thermally and thermodynamically significantly more stable than analogous duplexes of DNA and RNA. The salt-dependence and Watson-Crick-pairing fidelity of GNA duplexes are similar to those of DNA duplexes, but, apparently, the 2'-deoxyribonucleotide and the propylene glycol backbones are not compatible with each other. This conclusion is further supported by cross-pairing experiments. Accordingly, both (S)- and (R)-GNA strands do not generally pair with DNA. However, (S)-GNA, but not (R)-GNA, forms stable heteroduplexes with RNA in sequences that are low in G:C content. Altogether, the high stability and fidelity of GNA duplex formation in combination with the economical accessibility of propylene glycol building blocks for oligonucleotide synthesis render GNA an attractive candidate for the design of self-assembling materials. They further suggest that GNA could be considered as a potential candidate for a predecessor of RNA during the evolution of life on Earth.

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Two MRI contrast agents (CAs) composed of Gd-DO3A conjugated to amino acid building blocks derived from glutamic acid (CA1) and lysine (CA2) have been synthesized by using novel alkyne and propionate linkers, and subsequently characterized. In vitro cell viability assays showed insignificant cytotoxicity of both CAs at low concentrations up to 0.2 mM. The longitudinal relaxivities (r(1) ) of CA1 and CA2 measured at 9.4 T are 6.4 and 5.4 mM(-1)  s(-1) in H(2) O at 25 °C, respectively. Both r(1) values are higher than those of CAs in clinical use: Gd-DTPA (Magnevist, Bayer Schering, Germany) and Gd-DOTA (Dotarem, Guerbet, France). In vivo imaging in Wistar rats demonstrated considerable signal enhancement (∼50 %) in the brain artery by CA2, but lower signal enhancement (∼30 %) by CA1. In contrast to Dotarem, which showed a similar signal enhancement as CA2, the enhancement by CA2 remained high (∼30 %), even at 52 min post-injection. This demonstrates that CA2 has a much longer blood half-life (68.1 min), which could be advantageous for angiography and tissue targeting.

A mild oxidation of alcohols to the respective carbonyl compounds with o-iodoxybenzoic acid (IBX) catalyzed by n-Bu 4 NBr in a water/dichloromethane (1:1) mixture is described. The method offers the advantage of a simple, inexpensive catalyst and the diminution of organic solvent employed in the reaction.

The chiral amino acid-derived 2-iodoxybenzamides 2a-e were prepared and employed for investigation of their synthetic potential for the oxidation of sec-alcohols. The results indicate that they can readily oxidize sec-alcohols to the corresponding ketones in good to excellent yields, however, with lack of selectivity.