ACS Publications. Most Trusted. Most Cited. Most Read
Privileged Structures as Peptide Backbone Constraints: Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone Peptides

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:ACS Comb. Sci. 2014, 16, 7, 359-366
    Research Article

    Privileged Structures as Peptide Backbone Constraints: Polymer-Supported Stereoselective Synthesis of Benzimidazolinopiperazinone Peptides
    Click to copy article linkArticle link copied!

    View Author Information
    † Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University, 17 Listopadu 12, 771 46 Olomouc, Czech Republic
    ‡ Farmak, Na Vlčinci 16/3, Klášterní Hradisko, 779 00 Olomouc, Czech Republic
    § Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States
    *E-mail: [email protected]
    Other Access OptionsSupporting Information (1)

    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2014, 16, 7, 359–366
    Click to copy citationCitation copied!
    https://doi.org/10.1021/co500023k
    Published April 11, 2014
    Copyright © 2014 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A molecular scaffold comprising a privileged structure was designed and synthesized to serve as a peptide backbone conformational constraint. The synthesis of highly functionalized 2,3,10,10a-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrazin-4(1H)-ones on a solid-phase support was performed via a tandem N-acyl-N-aryliminium ion cyclization–nucleophilic addition reaction. The synthesis proceeded with full stereocontrol of the newly formed stereogenic center. Conventional and microwave-assisted syntheses were compared with respect to efficiency and the optical integrity of the target compounds. Significant epimerization was observed during acylation with (S)- and (R)-2-bromopropionic acids under microwave conditions.

    Copyright © 2014 American Chemical Society

    Subjects

    what are subjects

    Keywords

    what are keywords

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Copies of NMR spectra associated with this article. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article is cited by 18 publications.

    1. Eva Schütznerová, Adam Přibylka, Noelia S. Medran, Viktor Krchňák. Greening Solid-Phase Organic Synthesis: Environmentally Conscious Synthesis of Pharmaceutically Relevant Privileged Structures 5,6-Dihydropyridin-2(1H)-ones and Quinolin-2(1H)-ones. The Journal of Organic Chemistry 2020, 85 (18) , 11867-11881. https://doi.org/10.1021/acs.joc.0c01623
    2. Shashank Tripathi, Mayur D. Ambule, Ajay Kumar Srivastava. Construction of Highly Functionalized Piperazinones via Post-Ugi Cyclization and Diastereoselective Nucleophilic Addition. The Journal of Organic Chemistry 2020, 85 (11) , 6910-6923. https://doi.org/10.1021/acs.joc.0c00108
    3. Sergii Okorochenkov, Viktor Krchňák. Application of Glaser–Hay Diyne Coupling To Constrain Nα-Amino Acid Amides via a N–N Bridge. ACS Combinatorial Science 2019, 21 (4) , 316-322. https://doi.org/10.1021/acscombsci.8b00179
    4. Eva Schütznerová, Pedro Verdía, and Viktor Krchňák . Fused Ring Molecular Scaffold with 3D Architecture for Constrained Peptidomimetics: Polymer-Supported Stereoselective Synthesis of Tetrahydrobenzo[e]pyrazino[2,1-c][1,2,4]thiadiazinone 6,6-dioxide via N-Acyl Iminiums. ACS Combinatorial Science 2016, 18 (10) , 655-659. https://doi.org/10.1021/acscombsci.6b00126
    5. Veronika Fülöpová and Miroslav Soural . Mining the Chemical Space: Application of 2/4-Nitrobenzenesulfonamides in Solid-Phase Synthesis. ACS Combinatorial Science 2015, 17 (10) , 570-591. https://doi.org/10.1021/acscombsci.5b00089
    6. Agustina La-Venia, Pilar Ventosa-Andrés, Ludmila Hradilová, and Viktor Krchňák . From Amino Acids to Nature-Inspired Molecular Scaffolds: Incorporation of Medium-Sized Bridged Heterocycles into a Peptide Backbone. The Journal of Organic Chemistry 2014, 79 (21) , 10378-10389. https://doi.org/10.1021/jo501983j
    7. Jianhao Liang, Peifeng Tang, Jinxia Fu, Xinmeng Lan, Yu Wu, Qin Zhang, Shimin Kang. Valorization of polylactic acid to 2-bromopropionates and lactates. Biomass Conversion and Biorefinery 2024, 185 https://doi.org/10.1007/s13399-024-05454-z
    8. Naděžda Cankařová, Viktor Krchňák. Regioselective Cyclic Iminium Formation of Ugi Advanced Intermediates: Rapid Access to 3,4-Dihydropyrazin-2(1H)-ones and Other Diverse Nitrogen-Containing Heterocycles. Molecules 2023, 28 (7) , 3062. https://doi.org/10.3390/molecules28073062
    9. Abigail J. Herbert, Sarah A. Shepherd, Victoria A. Cronin, Matthew R. Bennett, Rehana Sung, Jason Micklefield. Engineering Orthogonal Methyltransferases to Create Alternative Bioalkylation Pathways. Angewandte Chemie 2020, 132 (35) , 15060-15066. https://doi.org/10.1002/ange.202004963
    10. Abigail J. Herbert, Sarah A. Shepherd, Victoria A. Cronin, Matthew R. Bennett, Rehana Sung, Jason Micklefield. Engineering Orthogonal Methyltransferases to Create Alternative Bioalkylation Pathways. Angewandte Chemie International Edition 2020, 59 (35) , 14950-14956. https://doi.org/10.1002/anie.202004963
    11. Joana F. Campos, Sabine Berteina-Raboin. Tandem Catalysis: Synthesis of Nitrogen-Containing Heterocycles. Catalysts 2020, 10 (6) , 631. https://doi.org/10.3390/catal10060631
    12. Indrajeet J. Barve, Chung‐Ming Sun. Solid‐Supported Synthesis. 2018, 469-507. https://doi.org/10.1002/9781119288152.ch18
    13. Eva Schütznerová, Allen G. Oliver, Greg A. Slough, Viktor Krchňák. Traceless Solid-Phase Synthesis of Fused Chiral Macrocycles via Conformational Constraint-Assisted Cyclic Iminium Formation. Chemistry - A European Journal 2017, 23 (52) , 12876-12885. https://doi.org/10.1002/chem.201702461
    14. A.M. Jones. Privileged Structures and Motifs (Synthetic and Natural Scaffolds). 2017, 116-152. https://doi.org/10.1016/B978-0-12-409547-2.12316-9
    15. Pilar Ventosa‐Andrés, Agustina La‐Venia, Carlos Alfonso Barea Ripoll, Ludmila Hradilová, Viktor Krchňák. Synthesis of Nature‐Inspired Medium‐Sized Fused Heterocycles from Amino Acids. Chemistry – A European Journal 2015, 21 (37) , 13112-13119. https://doi.org/10.1002/chem.201501746
    16. Pilar Ventosa-Andrés, Carlos Alfonso Barea Ripoll, Agustina La-Venia, Viktor Krchňák. Solid-phase synthesis of fused 1,4-diazepanone peptidomimetics via tandem N-iminium ion cyclization–nucleophilic addition. Tetrahedron Letters 2015, 56 (40) , 5424-5428. https://doi.org/10.1016/j.tetlet.2015.08.015
    17. Agustina La-Venia, Pilar Ventosa-Andrés, Viktor Krchňák. Peptidomimetics via Iminium Ion Chemistry on Solid Phase: Single, Fused, and Bridged Heterocycles. 2015, 105-126. https://doi.org/10.1007/7081_2015_194
    18. N.K. Terrett. Combinatorial Chemistry Online Volume 16, Issue 9, September 2014. Combinatorial Chemistry - an Online Journal 2014, 16 (9) , 33-35. https://doi.org/10.1016/j.comche.2014.08.001
    Download PDF
    Go to ACS Combinatorial Science
    Get e-Alerts
    Get e-Alerts

    ACS Combinatorial Science

    Cite this: ACS Comb. Sci. 2014, 16, 7, 359–366
    Click to copy citationCitation copied!
    https://doi.org/10.1021/co500023k
    Published April 11, 2014
    Copyright © 2014 American Chemical Society
    Request reuse permissions

    Article Views

    615

    Altmetric

    -

    Citations

    18
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.