Search results for "dipeptide"
showing 10 items of 99 documents
The young hard active Sun: soft X-ray irradiation of tryptophan in water solutions
2010
AbstractThe X-ray emission of the young Sun was much harder and intense than today and might have played a significant role in the evolution of complex organics in protoplanetary environments. We investigate the effects of soft X-rays on tryptophan molecules in aqueous solutions at room temperature. As results of the irradiation experiments we detect several light species indicative of fragmentation, together with large molecular structures such as tryptophan dipeptide and tripeptide. Complexification is more evident in H2O solution than in D2O, probably due to isotopic effects. The abundances of peptides depend on the irradiation dose and decrease with increasing energy deposition. Radical…
Unusual activity pattern of leucine aminopeptidase inhibitors based on phosphorus containing derivatives of methionine and norleucine
2010
Ligands containing bulky aliphatic P1 residues exhibit a high affinity towards cytosolic leucine aminopeptidase, a bizinc protease of biomedical significance. According to this specificity, a series of phosphonic and phosphinic compounds have been put forward as novel putative inhibitors of the enzyme. These phosphonic and phosphinic compounds were derivatives of methionine and norleucine as both single amino acids and dipeptides. The designed inhibitors were synthesised and tested towards the peptidase isolated from porcine kidneys using an improved separation procedure affording superior homogeneity. Unexpectedly, organophosphorus derivatives of methionine and norleucine exhibited moderat…
Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C
2023
In this paper, we present the solvolysis reaction of dipeptide analogues of fluorinated aminophosphonates with simultaneous quantitative deprotection of the amino group. To the best of our knowledge, this work is the first reported example of the application of fluorinated aminophosphonates in cathepsin C inhibition studies. The new molecules show moderate inhibition of the cathepsin C enzyme, which opens the door to consider them as potential therapeutic agents. Overall, our findings provide a new avenue for the development of fluorinated aminophosphonate-based inhibitors. This article is part of the thematic issue "Organophosphorus chemistry: from model to application".
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…
ChemInform Abstract: Solution-, Solid-Phase, and Fluorous Synthesis of β,β-Difluorinated Cyclic Quaternary α-Amino Acid Derivatives: A Comparative St…
2008
The diastereoselective synthesis of cyclic β,β-difluorinated α-amino acid derivatives bearing a quaternary stereocenter is described. The process relies on the chemo- and diastereoselective addition of allylic organometallic reagents to fluorinated α-imino esters and a subsequent ring-closing metathesis reaction (RCM). Complete selectivity in the nucleophilic addition was achieved with (R)-phenylglycinol methyl ether as a chiral auxiliary. The resulting amino acids were introduced into peptide chains, which could facilitate the preparation of potentially bioactive dipeptide derivatives. In addition, the solution synthesis of these cyclic fluorinated α-amino acids was successfully adapted to…
Straightforward Stereoselective Access to Cyclic Peptidomimetics
2009
The preparation of cyclic dipeptide mimetics from chiral imino lactones derived from (R)-phenylglycinol is described. Key steps of the synthetic route included the fully stereoselective construction of a quaternary center, the formation of six-, seven-, or eight-membered lactams by means of an RCM cyclization, and the introduction of a new amino group within the lactam ring. The synthesis of a tripeptide mimetic is also reported.
o-Boronato- and o-Trifluoroborato-Phosphonium Salts Supported by L-α-Amino Acid Side Chain.
2015
The synthesis of o-boronato- and o-trifluoroborato-phosphonium salts supported by the L-amino acid side chain is described. The synthesis of these new class of amino acid derivatives was achieved by stereoselective quaternization of o-(pinacolato)boronatophenylphosphine with β- or γ-iodo amino acid derivatives which are prepared from L-serine or L-aspartic acid, respectively. The quaternization of the phosphine was performed using either iodo amino ester or carboxylic acid derivatives. In addition, free carboxylic acid and amine derivatives were obtained by saponification or HCl acidolysis of o-boronato-phosphonium amino esters, respectively. The usefulness of these compounds in peptide cou…
Modular Hemisyntheses of Boronato- and Trifluoroborato-SubstitutedL-NHBoc Amino Acid and Peptide Derivatives
2013
Modular hemisyntheses of boronato- and trifluoroborato-substituted amino acid and peptide derivatives by using Wittig and C–H iridium-catalyzed borylation as key reactions, are described. Amino ester precursors bearing an aromatic moiety on a lateral chain were prepared by reaction of a new L-NHBoc-amino acid Wittig reagent with the corresponding aromatic aldehydes. After esterification and hydrogenation, the borylation of amino esters was achieved with yields up to 82 % by using the catalysed reaction of bis(pinacolato) diborane reagent (B2Pin2) in the presence of an iridium complex. Interestingly, this iridium-catalyzed borylation was also performed with a dipeptide in 78 % yield. Finally…
Stannacycloalkyl and stannepinyl derivatives of dipeptides
1994
Stannacyclohexyl and stannacycloheptyl derivatives of dipeptides (CH2)nSnAA · xH2O (H2AA = H2GlyGly, with n = 5, x = 2 or n = 6, x = 1; H2AA = H2GlyAla, H2GlyVal, H2GlyMet, with n = 5, 6, x = 1) and stannepinyl glycylglycinate monohydrate have been obtained by the reaction of (CH2)nSnCl2 or stannepinyl dichloride with Na2AA. According to infrared and 119Sn Mossbauer data of the solid compounds, AA acts as a tridentate ONN ligand and tin has a trigonalbipyramidal environment. An analogous structure has been inferred from 1H, 13C, and 119Sn NMR data for the undissociated molecules in methanol solution.
Synthesis of peptides with α,β‐dehydroamino acids, I. synthesis of N‐benzyloxycarbonyl and N‐trifluoroacetyl dipeptides of dehydroalanine and dehydro…
1984
Condensation of amides of N-(benzyloxycarbonyl)- and N-(trifluoroacetyl)amino acid with pyruvic and phenylpyruvic acid yields, in the presence of p-toluenesulfonic acid as a catalyst, N-(benzyloxycarbonyl)- and N-(trifluoroacetyl)dehydro dipeptides with C-terminal Δ Ala and ΔPhe, respectively (Table 2 and 3). Synthese von Peptiden mit α,β-Dehydroaminosauren, I. - Synthese von N-(Benzyloxycarbonyl)-und N-(Trifluoracetyl) dipeptiden von Dehydroalanin und Dehydrophenylalanin Die Kondensation von Nα-(Benzyloxycarbonyl)- und Nα-(Trifluoracetyl)aminosaureamiden mit Brenztrauben- und Phenylbrenztraubensaure in Gegenwart von p-Toluolsulfonsaure als Katalysator fuhrt zu N-(Benzyloxycarbonyl)- und N-…