Effect of Metals, Metalloids and Metallic Nanoparticles on Microalgae Growth and Industrial Product Biosynthesis: A Review

peer reviewedMicroalgae are a source of numerous compounds that can be used in many branches of industry. Synthesis of such compounds in microalgal cells can be amplified under stress conditions. Exposure to various metals can be one of methods applied to induce cell stress and synthesis of target products in microalgae cultures. In this review, the potential of producing diverse biocompounds (pigments, lipids, exopolymers, peptides, phytohormones, arsenoorganics, nanoparticles) from microalgae cultures upon exposure to various metals, is evaluated. Additionally, different methods to alter microalgae response towards metals and metal stress are described. Finally, possibilities to sustain high growth rates and productivity of microalgal cultures in the presence of metals are discussed

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

Resorcin[4]arenes (R[4]A) are macrocyclic compounds with a cavity structure. Despite a relatively small cavity, these compounds are capable of forming complexes with small organic molecules. The current paper focuses on the synthesis of complexes between R[4]A and secondary aliphatic amines (sec-amines). Through NMR spectroscopy, it was observed that “in-out” complexes are formed depending on the solvent. It was also found that the stoichiometry of the formed complexes depends on the size of the amine molecule. The automated interaction sites screening (aISS) made it possible to generate molecular ensembles of complexes. The geometry of the ensembles was first optimized with the r2scan-3c functional and, finally, the structure with the lowest energy, with the functional PBE0-D4/mTZVPP/CPCM. The Hartree–Fock plus London dispersion (HFLD) method was used for the study of non-covalent interactions (NCI). The calculations lead to the conclusion that a reduction in electrostatic interactions and an increase in exchange and dispersion interactions in CHCl3 in relation to DMSO are the driving forces behind the placement of sec-amine molecules into the R[4]A cavity and the formation of “in” type complexes

Supporting Information from Theoretical calculations of formation and reactivity of <i>o</i>-quinomethide derivatives of resorcin[4]arene with reference to empirical data

This paper describes theoretical reaction pathways of alkoxybenzyl derivatives of resorcin[4]arene leading to the formation of o-quinomethide derivatives of resorcin[4]arene (o-QMR[4]A). For each case, the activation energies for the formation of one o-QMR[4]A unit and the activation energies for the backward reaction were calculated. Based on the calculated reaction pathways, the reaction mechanism of o-QMR[4]A formation was proposed. Using the example of o-QMR[4]A generated from a methoxy derivative of resorcin[4]arene, the activation energies with selected nucleophiles were calculated and the reaction mechanisms discussed. Reaction path calculations were performed using the nudged elastic band method and semiempirical extended tight-binding method (GFN2-xTB). Using hydroxybenzyl derivatives of resorcin[4]arene as an example, a comparison of calculated activation energies by selected density-functional theory methods with GFN2-xTB and B97-3c geometries was performed. B97-3c and wB97XD methods were used to calculate the energies of the reactants (R), transition states (TS) and products (P) of the analysed reactions. Theoretical reaction mechanisms were discussed with respect to the orbital-weighted Fukui dual descriptor (Δfw) and experimental data

Intramolecular Hydrogen Bond Driven Conformational Selectivity of Coumarin Derivatives of Resorcin[4]arene

In this study, the synthesis and structure of 4-aminocoumarin derivatives of resorcin[4]arene were investigated. Spectroscopic analysis and quantum mechanical calculations showed that this molecule undertakes a crown-in conformation in chloroform. The conformations of the aminocoumarin derivative of resorcin[4]arene were compared with a hydroxycoumarin derivative of resorcin[4]arene, and the effect of the substituent on the conformational selectivity of the coumarin derivatives of resorcin[4]arene was demonstrated. Both UV-VIS and fluorescence spectroscopy for the coumarin derivative of resorcin[4]arene (3) were performed, and a strong fluorescence quenching of derivative 3 compared to 4-aminocoumarin was observed

Synthesis and structural investigation of the cyclochiral boron resorcinarenes obtained from L-amino acids and phenylboronic acid

Wzorek A, Mattay J, Iwanek W. Synthesis and structural investigation of the cyclochiral boron resorcinarenes obtained from L-amino acids and phenylboronic acid. Tetrahedron Asymmetry. 2012;23(3-4):271-277.A diastereoselective synthesis and structural investigation of novel boron derivatives of resorcinarenes from L-amino acids and phenylboronic acid is described. (C) 2012 Elsevier Ltd. All rights reserved

Synthesis of Resorcinarene Derivatives by the Catalyzed Mannich Reaction, Part 2: Resorcinarene Derivatives with Unsaturated Bonds

Urbaniak M, Mattay J, Iwanek W. Synthesis of Resorcinarene Derivatives by the Catalyzed Mannich Reaction, Part 2: Resorcinarene Derivatives with Unsaturated Bonds. Synthetic Communications. 2008;38(24):4345-4351.The conditions of a simple synthesis of alkenyloxymethyl and the alkynyloxymethyl derivatives of resorcinarene by the Mannich reaction catalyzed with iminodiacetic acid are described. The synthesis presented in this article is effective and uses readily available and inexpensive substrates

Synthesis of Resorcinarene Derivatives via the Catalyzed Mannich Reaction, Part 3: Glycol Derivatives of Resorcinarene

Urbaniak M, Mattay J, Iwanek W. Synthesis of Resorcinarene Derivatives via the Catalyzed Mannich Reaction, Part 3: Glycol Derivatives of Resorcinarene. Synthetic Communications. 2011;41(5):670-676.[image omitted] A series of resorcinarene glycol derivatives have been synthesized as secondary substitution products via a Mannich reaction catalyzed by iminodiacetic acid. The products are potentially useful candidates as podands for supramolecular chemistry. The synthesis presented in this article is effective and uses readily available and inexpensive substrates

Diastereoselective synthesis of boron-derivatives of resorcinarenes from amino alcohols and triethylborane

Wzorek A, Mattay J, Iwanek W. Diastereoselective synthesis of boron-derivatives of resorcinarenes from amino alcohols and triethylborane. Tetrahedron Asymmetrie. 2007;18(7):815-820.A diastereoselective synthesis of novel boron derivatives of resorcinarenes from chiral amino alcohols and triethylborane is described. (c) 2007 Elsevier Ltd. All rights reserved

Synthesis and Structure of Tetratosyl Bora Derivatives of Resorcinarenes From L-Proline and L-Prolinol

Gawdzik B, Wzorek A, Mattay J, Iwanek W. Synthesis and Structure of Tetratosyl Bora Derivatives of Resorcinarenes From L-Proline and L-Prolinol. Organic Preparations and Procedures International. 2009;41(3):217-227