Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties
Mungalpara, D., Valkonen, A., Rissanen, K., & Kubik, S. (2017). Efficient stabilisation of a dihydrogenphosphate tetramer and a dihydrogenpyrophosphate dimer by a cyclic pseudopeptide containing 1,4-disubstituted 1,2,3-triazole moieties. Chemical Science, 8(9), 6005-6013. https://doi.org/10.1039/C7SC02700A
Published inChemical Science
© the Authors, 2017. This is an open access article distributed under the terms of a Creative Commons License.
A cyclic pseudooctapeptide 2 is described containing 1,4-disubstituted 1,2,3-triazole moieties. This compound features eight converging hydrogen bond donors along the ring, namely four amide NH and four triazole CH groups, which enable 2 to engage in interactions with anions. While fully deprotonated sulfate anions exhibit only moderate affinity for 2, protonated anions such as dihydrogenpyrophosphate and dihydrogenphosphate anions are strongly bound. Complexation of the phosphate-derived anions involves sandwiching of a dihydrogenpyrophosphate dimer or a dihydrogenphosphate tetramer between two pseudopeptide rings. X-ray crystallography provided structural information, while 1 H NMR spectroscopy, mass spectrometry, and isothermal titration calorimetry demonstrated that these complexes are stable in solution (2.5 vol% water/ DMSO) and can even be transferred without decomposition into the gas phase. The observed high thermodynamic stabilities are attributed to the mutual reinforcement of the interactions between the individual complex components, namely, hydrogen-bonding between the anions, multiple hydrogen bonding interactions between the anion aggregates and the triazole CH and NH hydrogen bond donors of 2, and potential dispersive interactions between the closely arranged pseudopeptide rings. Pseudopeptide 2 thus represents a promising lead for the construction of phosphate receptors, whose binding selectivity makes use of the unique ability of certain anions to assemble into higher aggregates. ...
PublisherRoyal Society of Chemistry
Publication in research information system
MetadataShow full item record
Except where otherwise noted, this item's license is described as © the Authors, 2017. This is an open access article distributed under the terms of a Creative Commons License.
Showing items with similar title or keywords.
X-ray Crystal Structure and Hirshfeld Analysis of Gem-Aminals-Based Morpholine, Pyrrolidine, and Piperidine Moieties Al-Majid, Abdullah Mohammed; Haukka, Matti; Soliman, Saied M.; Alamary, Abdullah Saleh; Alshahrani, Saeed; Ali, M.; Islam, Mohammad Shahidul; Barakat, Assem (MDPI AG, 2021)The gem-aminals of 1,2-dimorpholinoethane (1) and 1-morpholino-3-morpholinium bromide propane (2) were synthesized by reaction of two molar ratio of morpholine with the halogenating agents in the presence of basic condition ...
Characterization of the interaction of the antifungal and cytotoxic cyclic glycolipopeptide hassallidin with sterol-containing lipid membranes Humisto, Anu; Jokela, Jouni; Teigen, Knut; Wahlsten, Matti; Permi, Perttu; Sivonen, Kaarina; Herfindal, Lars (Elsevier BV, 2019)Hassallidins are cyclic glycolipopeptides produced by cyanobacteria and other prokaryotes. The hassallidin structure consists of a peptide ring of eight amino acids where a fatty acid chain, additional amino acids, and ...
N-Heterocyclic Carbene Catalyzed Asymmetric Synthesis of Pentacyclic Spirooxindoles via [3+3] Annulations of Isatin-Derived Enals and Cyclic N-Sulfonyl Ketimines Liu, Qiang; Chen, Xiangyu; Li, Sun; Rissanen, Kari; Enders, Dieter (Wiley - VCH Verlag GmbH & Co. KGaA, 2019)A convenient enantioselective route to new types of pentacyclic spirooxindoles via [3+3] annulation reactions of isatin-derived enals and cyclic N-sulfonyl ketimines, using N-heterocyclic carbene (NHC) catalysis has ...
Fluorine-containing functionalized cyclopentene scaffolds through ring contraction and deoxofluorination of various substituted cyclohexenes Remete, Attila Márió; Nonn, Melinda; Fustero, Santos; Haukka, Matti; Fülöp, Ferenc; Kiss, Lorand (Wiley-VCH, 2018)The fluorination of some highly‐functionalized cyclopentene derivatives, obtained from various substituted cyclohexenes through a ring‐opening/ring‐contraction procedure, has been investigated. The transformations were ...
Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis : An Efficient Asymmetric Route to Cyclohexenes Chen, Xiang-Yu; Li, Sun; Liu, Qiang; Kumar, Mukesh; Peuronen, Anssi; Rissanen, Kari; Enders, Dieter (Wiley, 2018)Ahighly efficient strategy for the kinetic resolu-tion of Michael adductswas realized using achiral N-het-erocyclic carbene catalyst.The kinetic resolution providesanew convenientroute to single diastereomers of cyclo-hexenes ...