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 H-G, Nieß A, Antes I, Latajka R, Sewald N (2018)
Chemistry - A European Journal 24(4): 953-961.
Zeitschriftenaufsatz
| Veröffentlicht | Englisch
Download
Es wurden keine Dateien hochgeladen. Nur Publikationsnachweis!
Autor*in
Kracker, OliverUniBi;
Gora, JerzyUniBi;
Krzciuk-Gula, Joanna;
Marion, Antoine;
Neumann, BeateUniBi;
Stammler, Hans-GeorgUniBi;
Nieß, AnkeUniBi;
Antes, Iris;
Latajka, Rafal;
Sewald, NorbertUniBi 
Einrichtung
Abstract / Bemerkung
Peptidotriazolamers are hybrid foldamers combining features of peptides and triazolamers-repetitive peptidomimetic structures with triazoles replacing peptide bonds. We report on the synthesis of a new class of peptidomimetics, containing 1,5-disubstituted 1,2,3-triazoles in an alternating fashion with amide bonds and the analysis of their conformation in solid state and solution. Homo-or heterochiral peptidotriazolamers were obtained from enantiomerically pure propargylamines with stereogenic centers in the prop-argylic position and alpha-azido esters by ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) under microwave conditions in high yields. With such building blocks the peptidotriazolamers are readily available by solution phase synthesis. While the conformation of the homochiral peptidotriazolamer Boc-Ala[5Tz] Phe-Val[5Tz] Ala-Leu[5Tz] Val-OBzl resembles that of a beta VIa1 turn, the heterochiral peptidotriazolamer Boc- D-Ala[5Tz] Phe-D-Val[5Tz] Ala-d-Leu[5Tz] Val-OBzl adopts a polyproline-like repetitive structure.
Stichworte
conformational analysis;
foldamers;
peptidomimetics;
ruthenium;
triazoles
Erscheinungsjahr
2018
Zeitschriftentitel
Chemistry - A European Journal
Band
24
Ausgabe
4
Seite(n)
953-961
ISSN
0947-6539
eISSN
1521-3765
Page URI
https://pub.uni-bielefeld.de/record/2919079
Zitieren
Kracker O, Gora J, Krzciuk-Gula J, et al. 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal. 2018;24(4):953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H. - G., Nieß, A., et al. (2018). 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal, 24(4), 953-961. https://doi.org/10.1002/chem.201704583
Kracker, Oliver, Gora, Jerzy, Krzciuk-Gula, Joanna, Marion, Antoine, Neumann, Beate, Stammler, Hans-Georg, Nieß, Anke, Antes, Iris, Latajka, Rafal, and Sewald, Norbert. 2018. “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics”. Chemistry - A European Journal 24 (4): 953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H. - G., Nieß, A., Antes, I., Latajka, R., and Sewald, N. (2018). 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal 24, 953-961.
Kracker, O., et al., 2018. 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal, 24(4), p 953-961.
O. Kracker, et al., “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics”, Chemistry - A European Journal, vol. 24, 2018, pp. 953-961.
Kracker, O., Gora, J., Krzciuk-Gula, J., Marion, A., Neumann, B., Stammler, H.-G., Nieß, A., Antes, I., Latajka, R., Sewald, N.: 1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics. Chemistry - A European Journal. 24, 953-961 (2018).
Kracker, Oliver, Gora, Jerzy, Krzciuk-Gula, Joanna, Marion, Antoine, Neumann, Beate, Stammler, Hans-Georg, Nieß, Anke, Antes, Iris, Latajka, Rafal, and Sewald, Norbert. “1,5-Disubstituted 1,2,3-Triazole-Containing Peptidotriazolamers: Design Principles for a Class of Versatile Peptidomimetics”. Chemistry - A European Journal 24.4 (2018): 953-961.
1 Zitation in Europe PMC
Daten bereitgestellt von Europe PubMed Central.
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., Front Chem 7(), 2019
PMID: 30972322
Schröder DC, Kracker O, Fröhr T, Góra J, Jewginski M, Nieß A, Antes I, Latajka R, Marion A, Sewald N., Front Chem 7(), 2019
PMID: 30972322
53 References
Daten bereitgestellt von Europe PubMed Central.
Gellman, Acc. Chem. Res. 31(), 1998
Targeting recognition surfaces on natural proteins with peptidic foldamers.
Checco JW, Gellman SH., Curr. Opin. Struct. Biol. 39(), 2016
PMID: 27390896
Checco JW, Gellman SH., Curr. Opin. Struct. Biol. 39(), 2016
PMID: 27390896
Therapeutic Potential of Foldamers: From Chemical Biology Tools To Drug Candidates?
Gopalakrishnan R, Frolov AI, Knerr L, Drury WJ 3rd, Valeur E., J. Med. Chem. 59(21), 2016
PMID: 27362955
Gopalakrishnan R, Frolov AI, Knerr L, Drury WJ 3rd, Valeur E., J. Med. Chem. 59(21), 2016
PMID: 27362955
Smith, J. Am. Chem. Soc. 114(), 1992
Nonpeptidic foldamers from amino acids: synthesis and characterization of 1,3-substituted triazole oligomers.
Angelo NG, Arora PS., J. Am. Chem. Soc. 127(49), 2005
PMID: 16332031
Angelo NG, Arora PS., J. Am. Chem. Soc. 127(49), 2005
PMID: 16332031
Solution- and solid-phase synthesis of triazole oligomers that display protein-like functionality.
Angelo NG, Arora PS., J. Org. Chem. 72(21), 2007
PMID: 17880241
Angelo NG, Arora PS., J. Org. Chem. 72(21), 2007
PMID: 17880241
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
Jochim AL, Miller SE, Angelo NG, Arora PS., Bioorg. Med. Chem. Lett. 19(21), 2009
PMID: 19800230
Smith, Chem. Rev. 23(), 1938
Huisgen, Angew. Chem. Int. Ed. Engl. 2(), 1963
AUTHOR UNKNOWN, Angew. Chem. 75(), 1963
Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(i)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides.
Tornoe CW, Christensen C, Meldal M., J. Org. Chem. 67(9), 2002
PMID: 11975567
Tornoe CW, Christensen C, Meldal M., J. Org. Chem. 67(9), 2002
PMID: 11975567
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
Rostovtsev VV, Green LG, Fokin VV, Sharpless KB., Angew. Chem. Int. Ed. Engl. 41(14), 2002
PMID: 12203546
AUTHOR UNKNOWN, Angew. Chem. 114(), 2002
Cu-catalyzed azide-alkyne cycloaddition.
Meldal M, Tornoe CW., Chem. Rev. 108(8), 2008
PMID: 18698735
Meldal M, Tornoe CW., Chem. Rev. 108(8), 2008
PMID: 18698735
The growing impact of click chemistry on drug discovery.
Kolb HC, Sharpless KB., Drug Discov. Today 8(24), 2003
PMID: 14678739
Kolb HC, Sharpless KB., Drug Discov. Today 8(24), 2003
PMID: 14678739
Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions.
Angell YL, Burgess K., Chem Soc Rev 36(10), 2007
PMID: 17721589
Angell YL, Burgess K., Chem Soc Rev 36(10), 2007
PMID: 17721589
AUTHOR UNKNOWN, 0
Bock, J. Org. Chem. 71(), 2006
Growing applications of "click chemistry" for bioconjugation in contemporary biomedical research.
Nwe K, Brechbiel MW., Cancer Biother. Radiopharm. 24(3), 2009
PMID: 19538051
Nwe K, Brechbiel MW., Cancer Biother. Radiopharm. 24(3), 2009
PMID: 19538051
Click chemistry, a powerful tool for pharmaceutical sciences.
Hein CD, Liu XM, Wang D., Pharm. Res. 25(10), 2008
PMID: 18509602
Hein CD, Liu XM, Wang D., Pharm. Res. 25(10), 2008
PMID: 18509602
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
Tron GC, Pirali T, Billington RA, Canonico PL, Sorba G, Genazzani AA., Med Res Rev 28(2), 2008
PMID: 17763363
The growing applications of click chemistry.
Moses JE, Moorhouse AD., Chem Soc Rev 36(8), 2007
PMID: 17619685
Moses JE, Moorhouse AD., Chem Soc Rev 36(8), 2007
PMID: 17619685
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
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
Ruthenium-catalyzed azide-alkyne cycloaddition: scope and mechanism.
Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV., J. Am. Chem. Soc. 130(28), 2008
PMID: 18570425
Boren BC, Narayan S, Rasmussen LK, Zhang L, Zhao H, Lin Z, Jia G, Fokin VV., J. Am. Chem. Soc. 130(28), 2008
PMID: 18570425
Click chemistry: 1,2,3-triazoles as pharmacophores.
Agalave SG, Maujan SR, Pore VS., Chem Asian J 6(10), 2011
PMID: 21954075
Agalave SG, Maujan SR, Pore VS., Chem Asian J 6(10), 2011
PMID: 21954075
Pedersen, Eur. J. Org. Chem. (), 2011
Ruthenium-Catalyzed Azide Alkyne Cycloaddition Reaction: Scope, Mechanism, and Applications.
Johansson JR, Beke-Somfai T, Said Stalsmeden A, Kann N., Chem. Rev. 116(23), 2016
PMID: 27960271
Johansson JR, Beke-Somfai T, Said Stalsmeden A, Kann N., Chem. Rev. 116(23), 2016
PMID: 27960271
Johansson, Eur. J. Org. Chem. (), 2014
Reginato, Tetrahedron 52(), 1996
Dickson, Tetrahedron Lett. 45(), 2004
Conversion of carbonyl compounds to alkynes: general overview and recent developments.
Habrant D, Rauhala V, Koskinen AM., Chem Soc Rev 39(6), 2010
PMID: 20502799
Habrant D, Rauhala V, Koskinen AM., Chem Soc Rev 39(6), 2010
PMID: 20502799
Jurczak, Chem. Rev. 89(), 1989
Protein prosthesis: 1,5-disubstituted[1,2,3]triazoles as cis-peptide bond surrogates.
Tam A, Arnold U, Soellner MB, Raines RT., J. Am. Chem. Soc. 129(42), 2007
PMID: 17914828
Tam A, Arnold U, Soellner MB, Raines RT., J. Am. Chem. Soc. 129(42), 2007
PMID: 17914828
Approaches to the total synthesis of chaetochalasin A.
Thomas EJ, Willis M., Org. Biomol. Chem. 12(38), 2014
PMID: 25119649
Thomas EJ, Willis M., Org. Biomol. Chem. 12(38), 2014
PMID: 25119649
Doherty, Eur. J. Org. Chem. (), 2017
"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
Nahrwold M, Bogner T, Eissler S, Verma S, Sewald N., Org. Lett. 12(5), 2010
PMID: 20131817
Ellman, Pure Appl. Chem. 75(), 2003
Highly diastereoselective addition of alkynylmagnesium chlorides to N-tert-butanesulfinyl aldimines: a practical and general access to chiral alpha-branched amines.
Chen BL, Wang B, Lin GQ., J. Org. Chem. 75(3), 2010
PMID: 20041724
Chen BL, Wang B, Lin GQ., J. Org. Chem. 75(3), 2010
PMID: 20041724
A flexible and stereoselective synthesis of azetidin-3-ones through gold-catalyzed intermolecular oxidation of alkynes.
Ye L, He W, Zhang L., Angew. Chem. Int. Ed. Engl. 50(14), 2011
PMID: 21381165
Ye L, He W, Zhang L., Angew. Chem. Int. Ed. Engl. 50(14), 2011
PMID: 21381165
AUTHOR UNKNOWN, Angew. Chem. 123(), 2011
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
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
Recycling the tert-butanesulfinyl group in the synthesis of amines using tert-butanesulfinamide.
Wakayama M, Ellman JA., J. Org. Chem. 74(7), 2009
PMID: 19323570
Wakayama M, Ellman JA., J. Org. Chem. 74(7), 2009
PMID: 19323570
Synthesis and applications of tert-butanesulfinamide.
Robak MT, Herbage MA, Ellman JA., Chem. Rev. 110(6), 2010
PMID: 20420386
Robak MT, Herbage MA, Ellman JA., Chem. Rev. 110(6), 2010
PMID: 20420386
Alper, Tetrahedron Lett. 37(), 1996
Improved solid-phase peptide synthesis method utilizing alpha-azide-protected amino acids.
Lundquist JT 4th, Pelletier JC., Org. Lett. 3(5), 2001
PMID: 11259061
Lundquist JT 4th, Pelletier JC., Org. Lett. 3(5), 2001
PMID: 11259061
Thermal rearrangement of tert-butylsulfinamide.
Arava VR, Gorentla L, Dubey PK., Beilstein J Org Chem 7(), 2011
PMID: 21286388
Arava VR, Gorentla L, Dubey PK., Beilstein J Org Chem 7(), 2011
PMID: 21286388
Basel, Synthesis (), 2001
Carpino, Tetrahedron 55(), 1999
A heterocyclic peptide nanotube.
Horne WS, Stout CD, Ghadiri MR., J. Am. Chem. Soc. 125(31), 2003
PMID: 12889966
Horne WS, Stout CD, Ghadiri MR., J. Am. Chem. Soc. 125(31), 2003
PMID: 12889966
Systematic replacement of amides by 1,4-disubstituted[1,2,3]triazoles in Leu-enkephalin and the impact on the delta opioid receptor activity.
Proteau-Gagne A, Rochon K, Roy M, Albert PJ, Guerin B, Gendron L, Dory YL., Bioorg. Med. Chem. Lett. 23(19), 2013
PMID: 23988352
Proteau-Gagne A, Rochon K, Roy M, Albert PJ, Guerin B, Gendron L, Dory YL., Bioorg. Med. Chem. Lett. 23(19), 2013
PMID: 23988352
Oxyma: an efficient additive for peptide synthesis to replace the benzotriazole-based HOBt and HOAt with a lower risk of explosion.
Subiros-Funosas R, Prohens R, Barbas R, El-Faham A, Albericio F., Chemistry 15(37), 2009
PMID: 19575348
Subiros-Funosas R, Prohens R, Barbas R, El-Faham A, Albericio F., Chemistry 15(37), 2009
PMID: 19575348
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
Marion A, Gora J, Kracker O, Frohr T, Latajka R, Sewald N, Antes I., J Chem Inf Model 58(1), 2017
PMID: 29112399
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
Horn HW, Swope WC, Pitera JW, Madura JD, Dick TJ, Hura GL, Head-Gordon T., J Chem Phys 120(20), 2004
PMID: 15267980
Export
Markieren/ Markierung löschen
Markierte Publikationen
Web of Science
Dieser Datensatz im Web of Science®Quellen
PMID: 29160605
PubMed | Europe PMC
Suchen in
Google Scholar