Mini-Reviews in Organic Chemistry - Volume 12, Issue 3, 2015

Proline chimeras are conformationally rigid amino acid analogues. Their application in medicinal chemistry for the synthesis of peptidomimetics is a well-known approach. Of particular interest are the natural Glu/Asp proline chimeras, namely Domoic acid and Kainic acid, for their toxic effect on the human health which have been used as probes for glutamatergic receptors studies. In this review, we analyze the most relevant synthetic approaches to Glu/Asp analogues.

α-Hydroxyphosphinates, displaying a wide range of activities from agriculture to medicine as fungicides or metalloenzyme inhibitors, are compounds of high interest. In particular, α- hydroxyalkylphosphinates, bis(α-hydroxyalkyl)phosphinates, optically active form of these compounds as well as their derivatives receive continuously growing synthetic attention. Their synthesis, although impressively old, has never been reviewed. This review covers mainly the data published over the last ten years (2004-2014).

The review offers an overview on the synthesis of phosphonated N,O-nucleosides, a new class of interesting, potential antiviral/ antitumor agents. The main synthetic method exploit a 1,3- dipolar cycloaddition reaction as key step. The cycloaddition process involves the use of phosphonated nitrones, or nitrones containing functional groups easily convertible into phosphonated group. Biological assays are presented, which show that phosphonated N,O-nucleosides represent a new promising template of nucleoside analogues.

A new methods for the synthesis of molecular pockets, molecular umbrellas as well as quasi podands of steroids derivatives have been described. Moreover, a molecular umbrellas and pockets derived from biogenic precursors and their applications are described. Intermolecular 1,3- dipolar cycloaddition gave a quasi podands with 1,2,3-triazole rings. The structures of the products were confirmed by spectral analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential of synthesized compounds has been accomplished on the basis of Prediction of Activity Spectra for Substances (PASS).

Controlling the assembly of basic structural building blocks in a systematic and orderly fashion is an emerging issue in various areas of science and engineering such as physics, chemistry, material science, biological engineering, and electrical engineering. The self-assembly technique, among many other kinds of ordering techniques, has several unique advantages and the M13 bacteriophage can be utilized as part of this technique. The M13 bacteriophage (Phage) can easily be modified genetically and chemically to demonstrate specific functions. This allows for its use as a template to determine the homogeneous distribution and percolated network structures of inorganic nanostructures under ambient conditions. Inexpensive and environmentally friendly synthesis can be achieved by using the M13 bacteriophage as a novel functional building block. Here, we discuss recent advances in the application of M13 bacteriophage self-assembly structures and the future of this technology.

Sphingolipids are important cell membrane components among the phospholipid bilayer. Sphingolipid themselves and breakdown products play a significant role in signal transduction. All sphingolipids have a sphingosine backbone which is a long chain amino alcohol. Structurally, Sphingadienes differ from sphingosines due to the extra unsaturation present in the long aliphatic hydrocarbon chain. Sphingadienes have been isolated from fungi, plants, insects, marine organisms, and humans; mostly as components of sphingolipids. The biosynthesis of sphingadienes takes place due to the action of desaturase on sphingosine. The growing interest on sphingadienes is due to its implication in the biological processes such as apoptosis, cell signaling which has a direct impact on the development of anticancer and anti-inflammatory agents. Recent literature shows the action of sphingadiene on colon cancer cells is based on Akt dependent pathway. Further, a plant derived sphingadiene has shown anti-inflammatory activity by significantly inhibiting tumor necrosis factor α. The recent multigram quantity synthesis will undoubtedly strengthen the research in this area as this naturally occurring minor cell components cannot be harnessed in enough quantities for detailed mechanistic studies on biological effects.

Glycochips can be used to investigate the carbohydrate-protein interactions in highthroughput mode. Carbohydrates can be immobilized on the support surface by covalent or noncovalent binding. The derivatizations of carbohydrates for immobilizing to form glycochips were summarized herein.