ACS Publications. Most Trusted. Most Cited. Most Read
Synthesis of Sulfonated Peptides Using a Trifluoromethyltoluene-Protected Amino Acid
My Activity
    Article

    Synthesis of Sulfonated Peptides Using a Trifluoromethyltoluene-Protected Amino Acid
    Click to copy article linkArticle link copied!

    • Ashley E. DeYong
      Ashley E. DeYong
      Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United States
    • Kaicheng Li
      Kaicheng Li
      Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United States
      More by Kaicheng Li
    • Elliot L. Chaikof*
      Elliot L. Chaikof
      Department of Surgery, Beth Israel Deaconess Medical Center, Harvard Medical School, Boston, Massachusetts 02215, United States
      Division of Health Sciences and Technology, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States
      Broad Institute of MIT and Harvard, Cambridge, Massachusetts 02142, United States
      *Email: [email protected]. Phone: (617) 632-9581. Fax: (617) 632-9701.
    Other Access OptionsSupporting Information (1)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 3, 1327–1332
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02529
    Published January 14, 2025
    Copyright © 2025 American Chemical Society

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    A scalable, seven step synthesis is reported for a trifluoromethyl toluene protected sulfonated phenylalanine building block whose utility was demonstrated in the synthesis of four CXCR4-derived sulfonopeptides. When compared to a conventional trichloroethyl protected building block, overall yield was improved by up to 4-fold. We believe this building block will prove to be of significant value for the synthesis of a variety of peptide targets containing phenylalanine sulfonate, a bioisostere of tyrosine sulfate, enabling orthogonal protection strategies and improving synthetic efficiency and yield.

    Copyright © 2025 American Chemical Society

    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!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c02529.

    • Full experimental details; 1H NMR, 13C NMR, and HRMS of all new compounds (PDF)

    Terms & Conditions

    Electronic Supporting Information files are available without a subscription to ACS Web Editions. The American Chemical Society holds a copyright ownership interest in any copyrightable Supporting Information. Files available from the ACS website may be downloaded for personal use only. Users are not otherwise permitted to reproduce, republish, redistribute, or sell any Supporting Information from the ACS website, either in whole or in part, in either machine-readable form or any other form without permission from the American Chemical Society. For permission to reproduce, republish and redistribute this material, requesters must process their own requests via the RightsLink permission system. Information about how to use the RightsLink permission system can be found at http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!

    This article has not yet been cited by other publications.

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2025, 90, 3, 1327–1332
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c02529
    Published January 14, 2025
    Copyright © 2025 American Chemical Society

    Article Views

    454

    Altmetric

    -

    Citations

    -
    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.