1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties

Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N (2019)
Frontiers in Chemistry 7: 155.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
Download
OA 13.54 MB
Autor*in
Schröder, David C.UniBi ; Kracker, OliverUniBi; Fröhr, TanjaUniBi; Góra, Jerzy; Jewginski, Michał; Nieß, AnkeUniBi; Antes, Iris; Latajka, Rafał; Marion, Antoine; Sewald, NorbertUniBi
Abstract / Bemerkung
Peptidotriazolamers are hybrid foldamers with features of peptides and triazolamers, containing alternation of amide bonds and 1,4-disubstituted 1H-1,2,3-triazoles with conservation of the amino acid side chains. We report on the synthesis of a new class of peptidomimetics, containing 1,4-disubstituted 1H-1,2,3-triazoles in alternation with amide bonds and the elucidation of their conformational properties in solution. Based on enantiomerically pure propargylamines bearing the stereogenic center in the propargylic position and α-azido esters, building blocks were obtained by copper-catalyzed azide-alkyne cycloaddition. With these building blocks the peptidotriazolamers were readily available by solution phase synthesis. A panel of homo- and heterochiral tetramers, hexamers, and heptamers was synthesized and the heptamer Boc-Ala-Val-Ψ[4Tz]Phe-LeuΨ[4Tz]Phe-LeuΨ[4Tz]Val-OAll as well as an heterochiral and a Gly-containing equivalent were structurally characterized by NMR-based molecular dynamics simulations using a specifically tailored force field to determine their conformational and solvation properties. All three variants adopt a compact folded conformation in DMSO as well as in water. In addition to the heptamers we predicted the conformational behavior of similar longer oligomers i.e., Boc-Ala-(AlaΨ[4Tz]Ala)6-OAll as well as Boc-Ala-(d-AlaΨ[4Tz]Ala)6-OAll and Boc-Ala-(GlyΨ[4Tz]Ala)6-OAll. Our calculations predict a clear secondary structure of the first two molecules in DMSO that collapses in water due to the hydrophobic character of the side chains. The homochiral compound folds into a regular helical structure and the heterochiral one shows a twisted “S”-shape, while the Gly variant exhibits no clear secondary structure.
Erscheinungsjahr
2019
Zeitschriftentitel
Frontiers in Chemistry
Band
7
Art.-Nr.
155
ISSN
2296-2646
eISSN
2296-2646
Finanzierungs-Informationen
Open-Access-Publikationskosten wurden durch die Deutsche Forschungsgemeinschaft und die Universität Bielefeld gefördert.
Page URI
https://pub.uni-bielefeld.de/record/2934768

Zitieren

Schröder DC, Kracker O, Fröhr T, et al. 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry. 2019;7: 155.
Schröder, D. C., Kracker, O., Fröhr, T., Góra, J., Jewginski, M., Nieß, A., Antes, I., et al. (2019). 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry, 7, 155. https://doi.org/10.3389/fchem.2019.00155
Schröder, David C., Kracker, Oliver, Fröhr, Tanja, Góra, Jerzy, Jewginski, Michał, Nieß, Anke, Antes, Iris, Latajka, Rafał, Marion, Antoine, and Sewald, Norbert. 2019. “1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties”. Frontiers in Chemistry 7: 155.
Schröder, D. C., Kracker, O., Fröhr, T., Góra, J., Jewginski, M., Nieß, A., Antes, I., Latajka, R., Marion, A., and Sewald, N. (2019). 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry 7:155.
Schröder, D.C., et al., 2019. 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry, 7: 155.
D.C. Schröder, et al., “1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties”, Frontiers in Chemistry, vol. 7, 2019, : 155.
Schröder, D.C., Kracker, O., Fröhr, T., Góra, J., Jewginski, M., Nieß, A., Antes, I., Latajka, R., Marion, A., Sewald, N.: 1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties. Frontiers in Chemistry. 7, : 155 (2019).
Schröder, David C., Kracker, Oliver, Fröhr, Tanja, Góra, Jerzy, Jewginski, Michał, Nieß, Anke, Antes, Iris, Latajka, Rafał, Marion, Antoine, and Sewald, Norbert. “1,4-Disubstituted 1H-1,2,3-Triazole Containing Peptidotriazolamers: A New Class of Peptidomimetics With Interesting Foldamer Properties”. Frontiers in Chemistry 7 (2019): 155.
Alle Dateien verfügbar unter der/den folgenden Lizenz(en):
Creative Commons Namensnennung - Nicht-kommerziell - Keine Bearbeitung 3.0 Unported (CC BY-NC-ND 3.0):
Volltext(e)
Access Level
OA Open Access
Zuletzt Hochgeladen
2019-09-06T09:19:06Z
MD5 Prüfsumme
fb8b35b4af5ac83c19fa7d720d895557


54 References

Daten bereitgestellt von Europe PubMed Central.

Evaluation of distances from ROESY experiments with the intensity-ratiomethod
Ämmälahti E., Bardet M., Molko D., Cadet J.., 1996
Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions.
Angell YL, Burgess K., Chem Soc Rev 36(10), 2007
PMID: 17721589
The 1,2,3-triazole ring as a peptido- and olefinomimetic element: discovery of click vanilloids and cannabinoids.
Appendino G, Bacchiega S, Minassi A, Cascio MG, De Petrocellis L, Di Marzo V., Angew. Chem. Int. Ed. Engl. 46(48), 2007
PMID: 17968870
Thermal rearrangement of tert-butylsulfinamide.
Arava VR, Gorentla L, Dubey PK., Beilstein J Org Chem 7(), 2011
PMID: 21286388
Conformationally homogeneous heterocyclic pseudotetrapeptides as three-dimensional scaffolds for rational drug design: receptor-selective somatostatin analogues.
Beierle JM, Horne WS, van Maarseveen JH, Waser B, Reubi JC, Ghadiri MR., Angew. Chem. Int. Ed. Engl. 48(26), 2009
PMID: 19266506
Straightforward strategy to substitute amide bonds by 1,2,3-triazoles in peptaibols analogs using Aibψ[Tz]-Xaa dipeptides.
Ben Haj Salah K, Legrand B, Das S, Martinez J, Inguimbert N., Biopolymers 104(5), 2015
PMID: 25784277
How are 1,2,3-triazoles accommodated in helical secondary structures?
Ben Haj Salah K, Das S, Ruiz N, Andreu V, Martinez J, Wenger E, Amblard M, Didierjean C, Legrand B, Inguimbert N., Org. Biomol. Chem. 16(19), 2018
PMID: 29693098
CuI-catalyzed alkyne–azide “Click” Cycloadditions from a mechanistic and synthetic perspective
Bock V., Hiemstra H., van J.., 2006
Click chemistry as a route to cyclic tetrapeptide analogues: synthesis of cyclo-[Pro-Val-psi(triazole)-Pro-Tyr].
Bock VD, Perciaccante R, Jansen TP, Hiemstra H, van Maarseveen JH., Org. Lett. 8(5), 2006
PMID: 16494474
1,2,3-Triazoles as peptide bond isosteres: synthesis and biological evaluation of cyclotetrapeptide mimics.
Bock VD, Speijer D, Hiemstra H, van Maarseveen JH., Org. Biomol. Chem. 5(6), 2007
PMID: 17340013
1,2,3-triazole as a peptide surrogate in the rapid synthesis of HIV-1 protease inhibitors.
Brik A, Alexandratos J, Lin YC, Elder JH, Olson AJ, Wlodawer A, Goodsell DS, Wong CH., Chembiochem 6(7), 2005
PMID: 15934050
Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors.
Brik A, Muldoon J, Lin YC, Elder JH, Goodsell DS, Olson AJ, Fokin VV, Sharpless KB, Wong CH., Chembiochem 4(11), 2003
PMID: 14613121

Case C., Cheatham T., Darden T., Duke R., Giese T., Gohlke H.., 2017
Bivalent peptidomimetic ligands of TrkC are biased agonists and selectively induce neuritogenesis or potentiate neurotrophin-3 trophic signals.
Chen D, Brahimi F, Angell Y, Li YC, Moscowicz J, Saragovi HU, Burgess K., ACS Chem. Biol. 4(9), 2009
PMID: 19735123
Application of the RESP methodology in the parametrization of organicsolvents
Fox T., Kollman P.., 1998
Click chemistry - what's in a name? triazole synthesis and beyond
Gil B., Arévalo M., López O.., 2007
NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities.
Gottlieb HE, Kotlyar V, Nudelman A., J. Org. Chem. 62(21), 1997
PMID: 11671879
Polypseudopeptides with variable stereochemistry: synthesis via click-chemistry, postfunctionalization and conformational behavior in solution
Hartwig S., Hecht S.., 2010
Click chemistry, a powerful tool for pharmaceutical sciences.
Hein CD, Liu XM, Wang D., Pharm. Res. 25(10), 2008
PMID: 18509602
Development of an improved four-site water model for biomolecular simulations: TIP4P-Ew.
Horn HW, Swope WC, Pitera JW, Madura JD, Dick TJ, Hura GL, Head-Gordon T., J Chem Phys 120(20), 2004
PMID: 15267980
Heterocyclic peptide backbone modifications in an alpha-helical coiled coil.
Horne WS, Yadav MK, Stout CD, Ghadiri MR., J. Am. Chem. Soc. 126(47), 2004
PMID: 15563148
VMD: visual molecular dynamics.
Humphrey W, Dalke A, Schulten K., J Mol Graph 14(1), 1996
PMID: 8744570
Matplotlib: A 2D Graphics Environment
Hunter J.., 2007
Evaluation of triazolamers as active site inhibitors of HIV-1 protease.
Jochim AL, Miller SE, Angelo NG, Arora PS., Bioorg. Med. Chem. Lett. 19(21), 2009
PMID: 19800230
Head-to-tail dimerization and organogelating properties of click peptidomimetics.
Ke Z, Chow HF, Chan MC, Liu Z, Sze KH., Org. Lett. 14(1), 2011
PMID: 22188338
Design, synthesis, and preliminary biological evaluation of a novel triazole analogue of ceramide.
Kim S, Cho M, Lee T, Lee S, Min HY, Lee SK., Bioorg. Med. Chem. Lett. 17(16), 2007
PMID: 17561396
The growing impact of click chemistry on drug discovery.
Kolb HC, Sharpless KB., Drug Discov. Today 8(24), 2003
PMID: 14678739
1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics.
Kracker O, Gora J, Krzciuk-Gula J, Marion A, Neumann B, Stammler HG, Nieß A, Antes I, Latajka R, Sewald N., Chemistry 24(4), 2017
PMID: 29160605
Synthesis and evaluation of 1,2,3-triazole containing analogues of the immunostimulant alpha-GalCer.
Lee T, Cho M, Ko SY, Youn HJ, Baek DJ, Cho WJ, Kang CY, Kim S., J. Med. Chem. 50(3), 2007
PMID: 17266209
Amber-Compatible Parametrization Procedure for Peptide-like Compounds: Application to 1,4- and 1,5-Substituted Triazole-Based Peptidomimetics.
Marion A, Gora J, Kracker O, Frohr T, Latajka R, Sewald N, Antes I., J Chem Inf Model 58(1), 2017
PMID: 29112399
The growing applications of click chemistry.
Moses JE, Moorhouse AD., Chem Soc Rev 36(8), 2007
PMID: 17619685
"Clicktophycin-52": a bioactive cryptophycin-52 triazole analogue.
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N., Org. Lett. 12(5), 2010
PMID: 20131817
Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research.
Nwe K, Brechbiel MW., Cancer Biother. Radiopharm. 24(3), 2009
PMID: 19538051

Oliphant T.., 2007
1,2,3-triazoles in peptidomimetic chemistry
Pedersen D., Abell A.., 2011
A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB., Angew. Chem. Int. Ed. Engl. 41(14), 2002
PMID: 12203546
Design,synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a β-strand: potential application to the design of novel inhibitors of proteolytic enzymes
Smith B., Keenan T., Holcomb R., Sprengeler P., Guzman M.., 1992
Click chemistry reactions in medicinal chemistry: applications of the 1,3-dipolar cycloaddition between azides and alkynes.
Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA., Med Res Rev 28(2), 2008
PMID: 17763363
Probing the Backbone Function of Tumor Targeting Peptides by an Amide-to-Triazole Substitution Strategy.
Valverde IE, Vomstein S, Fischer CA, Mascarin A, Mindt TL., J. Med. Chem. 58(18), 2015
PMID: 26309061
Efficient route to C2 symmetric heterocyclic backbone modified cyclic peptides.
van Maarseveen JH, Horne WS, Ghadiri MR., Org. Lett. 7(20), 2005
PMID: 16178569
Rapid assembly of matrix metalloprotease inhibitors using click chemistry.
Wang J, Uttamchandani M, Li J, Hu M, Yao SQ., Org. Lett. 8(17), 2006
PMID: 16898826
(RS)-(+)-2-Methyl-2-propanesulfinamide
Weix D., Ellman J.., 2005
Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics.
Wunsch M, Schroder D, Frohr T, Teichmann L, Hedwig S, Janson N, Belu C, Simon J, Heidemeyer S, Holtkamp P, Rudlof J, Klemme L, Hinzmann A, Neumann B, Stammler HG, Sewald N., Beilstein J Org Chem 13(), 2017
PMID: 29234470
An efficient and improved procedure for preparation of triflyl azide and application in catalytic diazotransferreaction
Yan R., Yang F., Wu Y., Zhang L., Ye X.., 2005
Ruthenium-catalyzed cycloaddition of alkynes and organic azides.
Zhang L, Chen X, Xue P, Sun HH, Williams ID, Sharpless KB, Fokin VV, Jia G., J. Am. Chem. Soc. 127(46), 2005
PMID: 16287266
Material in PUB:
Teil dieser Dissertation
Conformational Analysis of Peptidotriazolamers and *cyclic* RGD Peptides
Schröder DC (2021)
Bielefeld: Universität Bielefeld.
Export

Markieren/ Markierung löschen
Markierte Publikationen

Open Data PUB

Web of Science

Dieser Datensatz im Web of Science®
Quellen

PMID: 30972322
PubMed | Europe PMC

Suchen in

Google Scholar