15401-08-8Relevant articles and documents
Synthesis of Prolylproline
Gaidukevich,Popova,Zubreichuk,Knizhnikov
, p. 1005 - 1008 (2019)
Prolylproline has been synthesized by both classical peptide synthesis method utilizing tert-butoxycarbonyl or trifluoroacetyl protection of the NH group and carbodiimide-promoted peptide bond formation and by opening of the dioxopiperazine ring in octahydrodipyrrolo[1,2-a:1′,2′-d]pyrazine-5,10-dione obtained by thermolysis of proline methyl ester.
Permeation through phospholipid bilayers, skin-cell penetration, plasma stability, and CD spectra of α- And β-oligoproline derivatives
Kolesinska, Beata,Podwysocka, Dominika J.,Rueping, Magnus A.,Seebach, Dieter,Kamena, Faustin,Walde, Peter,Sauer, Markus,Windschiegl, Barbara,Meyer-ács, Mira,Vor Der Brüggen, Marc,Giehring, Sebastian
, p. 1 - 38 (2013)
After a survey of the special role, which the amino acid proline plays in the chemistry of life, the cell-penetrating properties of polycationic proline-containing peptides are discussed, and the widely unknown discovery by the Giralt group (J. Am. Chem. Soc. 2002, 124, 8876) is acknowledged, according to which fluorescein-labeled tetradecaproline is slowly taken up by rat kidney cells (NRK-49F). Here, we describe details of our previously mentioned (Chem. Biodiversity 2004, 1, 1111) observation that a hexa-β3-Pro derivative penetrates fibroblast cells, and we present the results of an extensive investigation of oligo-L- and oligo-D-α-prolines, as well as of oligo-β2h- and oligo-β3h-prolines without and with fluorescence labels (1-8; Fig. 1). Permeation through protein-free phospholipid bilayers is detected with the nanoFAST biochip technology (Figs. 2-4). This methodology is applied for the first time for quantitative determination of translocation rates of cell-penetrating peptides (CPPs) across lipid bilayers. Cell penetration is observed with mouse (3T3) and human foreskin fibroblasts (HFF; Figs. 5 and 6-8, resp.). The stabilities of oligoprolines in heparin-stabilized human plasma increase with decreasing chain lengths (Figs. 9-11). Time- and solvent-dependent CD spectra of most of the oligoprolines (Figs. 13 and 14) show changes that may be interpreted as arising from aggregation, and broadening of the NMR signals with time confirms this assumption. Copyright
Synthesis of novel proline-based imidazolium ionic liquids
Chaubey, Snehkrishn A.,Patra, Niranjan,Mishra, Roli
, p. 1409 - 1417 (2020)
Abstract: A series of eight novel proline functionalized dipeptide imidazolium ionic liquids (DPILs), i.e. Boc-[Pro-Pro-EMIM], Boc-[Pro-Val-EMIM], Boc-[Pro-Ala-EMIM], Boc-[Pro-Phe-EMIM] containing [Cl] and [NTf2] anions were synthesized via a f
Proline-Rich Short Peptides with Photocatalytic Activity for the Nucleophilic Addition of Methanol to Phenylethylenes
Hermann, Sergej,Sack, Daniel,Wagenknecht, Hans-Achim
, p. 2204 - 2207 (2018/06/04)
Short proline-rich peptides were synthesized and modified with 1-(N,N-dimethylamino)pyrene by copper(I)-catalyzed cycloaddition. They perform photoredox catalysis of the nucleophilic addition of methanol to 1,1-diphenylethylene derivatives into products with Markovnikov orientation. The common additive triethylamine is avoided because forward and backward electron transfer is controlled by substrate binding. A free carboxylic function in the substrate allows more precise substrate binding and defines the electron transfer path better than the unspecific exciplex formation with the substrate bearing a carboxylic ester. A proline-type turn is an advantage for photoredox catalysis, but a proline-induced helix is not required. This is the first successful example for introducing secondarily structured peptides to photoredox catalysis.
Peptide-catalyzed stereoselective Michael addition of aldehydes and ketones to heterocyclic nitroalkenes
Polá?ková, Viera,?melová, Patrícia,Górová, Renáta,?ebesta, Radovan
, p. 729 - 736 (2017/12/26)
Abstract: Stereoselective Michael addition of enolizable carbonyl compounds to a furane-derived nitroalkene was catalyzed by di- and tripeptide organocatalysts. The most competent catalysts were tripeptides possessing Pro–Pro–Glu structure. With aldehydes
Factors Affecting the Stabilization of Polyproline II Helices in a Hydrophobic Environment
Zanna, Nicola,Milli, Lorenzo,Del Secco, Benedetta,Tomasini, Claudia
, p. 1662 - 1665 (2016/04/26)
Several parameters have a critical importance for the stabilization of either polyproline I (PPI) or polyproline II (PPII) helices in a hydrophobic environment. Among them, it was found out that the concentration is crucial as polyprolines at 3 mM concent
Compounds, compositions and use
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Page/Page column, (2014/05/08)
A peptide comprising a unit of formula (I) and having a molecular weight of less than 2000 wherein each X is independently an organic group, e.g. a C1-6 alkyl or C1-6 alkenyl group, preferably —CH2—CH═CH2, or th
Asymmetric catalysis at the mesoscale: Gold nanoclusters embedded in chiral self-assembled monolayer as heterogeneous catalyst for asymmetric reactions
Gross, Elad,Liu, Jack H.,Alayoglu, Selim,Marcus, Matthew A.,Fakra, Sirine C.,Toste, F. Dean,Somorjai, Gabor A.
, p. 3881 - 3886 (2013/04/10)
Research to develop highly versatile, chiral, heterogeneous catalysts for asymmetric organic transformations, without quenching the catalytic reactivity, has met with limited success. While chiral supramolecular structures, connected by weak bonds, are highly active for homogeneous asymmetric catalysis, their application in heterogeneous catalysis is rare. In this work, asymmetric catalyst was prepared by encapsulating metallic nanoclusters in chiral self-assembled monolayer (SAM), immobilized on mesoporous SiO2 support. Using olefin cyclopropanation as an example, it was demonstrated that by controlling the SAM properties, asymmetric reactions can be catalyzed by Au clusters embedded in chiral SAM. Up to 50% enantioselectivity with high diastereoselectivity were obtained while employing Au nanoclusters coated with SAM peptides as heterogeneous catalyst for the formation of cyclopropane- containing products. Spectroscopic measurements correlated the improved enantioselectivity with the formation of a hydrogen-bonding network in the chiral SAM. These results demonstrate the synergetic effect of the catalytically active metallic sites and the surrounding chiral SAM for the formation of a mesoscale enantioselective catalyst.
Hybrid bombesin analogues: Combining an agonist and an antagonist in defined distances for optimized tumor targeting
Kroll, Carsten,Mansi, Rosalba,Braun, Friederike,Dobitz, Stefanie,Maecke, Helmut R.,Wennemers, Helma
supporting information, p. 16793 - 16796 (2013/12/04)
Radiolabeled hybrid ligands with defined distances between an agonist and an antagonist for the gastrin-releasing peptide receptor were found to have excellent tumor-targeting properties. Oligoprolines served as rigid scaffolds that allowed for tailoring distances of 10, 20, and 30 A between the recognition elements. In vitro and in vivo studies revealed that the hybrid ligand with a distance of 20 A between the recognition elements exhibits the highest yet observed tumor cell uptake and retention time in prostate cancer cells.
PEG prodrug of gambogic acid: Amino acid and dipeptide spacer effects
Ding, Ya,Zhang, Peng,Tang, Xiao-Yan,Zhang, Can,Ding, Song,Ye, Hai,Ding, Qi-Long,Shen, Wen-Bin,Ping, Qi-Neng
experimental part, p. 1694 - 1702 (2012/08/08)
The clinical application of gambogic acid (GA), a natural component with promising antitumor activity, was limited due to its extremely poor aqueous solubility, rapid elimination in vivo, and wide biodistribution. To solve these problems, 30 poly(ethylene
