showing 15 related works from this author
Dipeptides of S-Substituted Dehydrocysteine as Artzyme Building Blocks: Synthesis, Complexing Abilities and Antiproliferative Properties †
2021
Background: Dehydropeptides are analogs of peptides containing at least one conjugate double bond between α,β-carbon atoms. Its presence provides unique structural properties and reaction centre for chemical modification. In this study, the series of new class of dipeptides containing S-substituted dehydrocysteine with variety of heterocyclic moieties was prepared. The compounds were designed as the building blocks for the construction of artificial metalloenzymes (artzymes). Therefore, the complexing properties of representative compounds were also evaluated. Furthermore, the acknowledged biological activity of natural dehydropeptides was the reason to extend the study for antiproliferativ…
Crystal structure of N-(tert-butoxycarbonyl)phenylalanyldehydroalanine isopropyl ester (Boc–Phe–ΔAla–OiPr)
2014
In the crystal structure of the dehydrodipeptide (Boc-Phe-ΔAla-OiPr), the molecule has a trans configuration of the N-methylamide group. Its geometry is different from saturated peptides but is in excellent agreement with other dehydroalanine compounds. In the crystal, an N—H⋯O hydrogen bond links the molecules in a herringbone packing arrangement.
A novel approach for obtaining α,β-diaminophosphonates bearing structurally diverse side chains and their interactions with transition metal ions stu…
2020
Aminophosphonates are an important group of building blocks in medicinal and pharmaceutical chemistry. Novel representatives of this class of compounds containing nontypical side chains are still needed. The aza-Michael-type addition of amines to phosphonodehydroalanine derivatives provides a simple and effective approach for synthesizing N′-substituted α,β-diaminoethylphosphonates and thus affords general access to aminophosphonates bearing structurally diverse side chains. Thermodynamic analysis of the chosen aminophosphonates at physiological pH proves that they serve as potent chelators for copper(II) ions and moderate chelators for nickel(II) ions.
Addition of thiols to the double bond of dipeptide C-terminal dehydroalanine as a source of new inhibitors of cathepsin C.
2017
Addition of thiols to double bond of glycyl-dehydroalanine and phenyl-dehydroalanine esters provided micromolar inhibitors of cathepsin C. The structure-activity studies indicated that dipeptides containing N-terminal phenylalanine exhibit higher affinity towards the enzyme. A series of C-terminal S-substituted cysteines are responsible for varying interaction with S1 binding pocket of cathepsin C. Depending on diastereomer these compounds most likely act as slowly reacting substrates or competitive inhibitors. This was proved by TLC analysis of the medium in which interaction of methyl (S)-phenylalanyl-(R,S)-(S-adamantyl)cysteinate (7i) with the enzyme was studied. Molecular modeling enabl…
Michael additions to double bonds of esters of N-protected (s)-phenylalanyldehydroalanine (X-(s)-Phe-ΔAla-OMe) and its phosphonic acid counterpart (X…
2017
Electrophilic addition of amines, thiols and bromide to the double bonds of model dehydrodipeptides and dehydrophosphonodipeptide was studied. The double bond in these two classes of peptides reacted similarly and gave the same products. These results indicate that dehydropeptides are very good candidates as substrates for modifications of peptide side-chains.
Novel, automated, semi-industrial modular photobioreactor system for cultivation of demanding microalgae that produce fine chemicals - The next story…
2021
Abstract Recently, there has been increased interest in the use of microorganisms in the production of pharmaceuticals, nutraceuticals and energy supply products, which is due to their rapid growth rate and ability to biosynthesize fine chemicals or biotransform specific xenobiotics. To achieve the desired scale of production and optimization of microbial cultures, it is necessary to design bioreactors that enable process automation, control of working parameters, reduction of microbial and chemical contaminations, and culture independence of climate conditions. In response to this need, an original, modular airlift-type photobioreactor system was designed and manufactured. This novel semit…
Access to α-Aminophosphonic Acid Derivatives and Phosphonopeptides by [Rh(P–OP)]-Catalyzed Stereoselective Hydrogenation
2020
The hydrogenation of N-substituted vinylphosphonates using rhodium complexes derived from P–OP ligands L1, ent-L1, or (R,R)-Me-DuPHOS as catalysts has been successfully accomplished, achieving very high levels of stereoselectivity (up to 99% ee or de). The described synthetic strategy allowed for the efficient preparation of α-aminophosphonic acid derivatives and phosphonopeptides, which are valuable building blocks for the preparation of biologically relevant molecules.
Analytical procedures for short chain chlorinated paraffins determination - How to make them greener?
2019
Abstract The aim of the following paper was to gather current scientific information about the analytical protocols dedicated to measuring the content level of short-chain chlorinated paraffins (SCCPs) in various types of environmental samples. Moreover, the data about the basic validation parameters of applied procedures for SCCPs determination are listed. The main issue which is highlighted in the paper is the possibility of the application of green analytical chemistry (GAC) principals in the SCCPs measuring process to reduce the environmental impact of the applied methodology. Analytical methods dedicated to SCCPs determination contain a significant number of steps and require advanced …
Synthesis of dehydrodipeptide esters and their evaluation as inhibitors of cathepsin C
2015
The procedures for the synthesis of esters of dehydropeptides containing C-terminal (Z)-dehydrophenylalanine and dehydroalanine have been elaborated. These esters appeared to be moderate or weak inhibitors of cathepsin C, with some of them exhibiting slow-binding behavior. As shown by molecular modeling, they are rather bound at the surface of the enzyme and are not submersed in its binding cavities. Electronic supplementary material The online version of this article (doi:10.1007/s00044-015-1366-0) contains supplementary material, which is available to authorized users.
The overproduction of 2,4-DTBP accompanying to the lack of available form of phosphorus during the biodegradative utilization of aminophosphonates by…
2014
Although information about the ability of some filamentous fungi to biodegrade organophosphonates is available, the knowledge about accompanying changes in fungal metabolism is very limited. The aim of our study was to determine the utilization of the chosen, structurally diverse aminophosphonates by Aspergillus terreus (Thom), in the context of the behaviour of this fungus while growing in unfavourable conditions, namely the lack of easily available phosphates. We found that all the studied compounds were utilized by fungus as nutritive sources of phosphorus, however, their effect on the production of fungal biomass depended on their structure. We also observed an interesting change in the…
Crystal structure ofN-(tert-butoxycarbonyl)glycyl-(Z)-β-bromodehydroalanine methyl ester [Boc–Gly–(β-Br)(Z)ΔAla–OMe]
2014
In a dehydroamino acid with a C=C bond between the α- and β-C atoms, the amino acid residues are linked trans to each other and there are no strong intramolecular hydrogen bonds. The torsion angles indicate a non-helical conformation of the molecule.
CCDC 1529401: Experimental Crystal Structure Determination
2017
Related Article: Paweł Lenartowicz, Błażej Dziuk, Bartosz Zarychta, Maciej Makowski, Paweł Kafarski|2017|Phosphorus,Sulfur,Silicon,Relat.Elem.|192|706|doi:10.1080/10426507.2017.1308933
CCDC 1529397: Experimental Crystal Structure Determination
2017
Related Article: Paweł Lenartowicz, Błażej Dziuk, Bartosz Zarychta, Maciej Makowski, Paweł Kafarski|2017|Phosphorus,Sulfur,Silicon,Relat.Elem.|192|706|doi:10.1080/10426507.2017.1308933
CCDC 1935968: Experimental Crystal Structure Determination
2022
Related Article: Paweł Lenartowicz, Danuta Witkowska, Beata Żyszka-Haberecht, Błażej Dziuk, Krzysztof Ejsmont, Jolanta Świątek-Kozłowska, Paweł Kafarski|2020|RSC Advances|10|24045|doi:10.1039/D0RA03764H
CCDC 1935969: Experimental Crystal Structure Determination
2022
Related Article: Paweł Lenartowicz, Danuta Witkowska, Beata Żyszka-Haberecht, Błażej Dziuk, Krzysztof Ejsmont, Jolanta Świątek-Kozłowska, Paweł Kafarski|2020|RSC Advances|10|24045|doi:10.1039/D0RA03764H