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    The 9-Fluorenylmethoxycarbonyl (Fmoc) Group in Chemical Peptide Synthesis - Its Past, Present, and Future

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    Author
    Li, W; O'Brien-Simpson, NM; Hossain, MA; Wade, JD
    Date
    2020-01-01
    Source Title
    Australian Journal of Chemistry: an international journal for chemical science
    Publisher
    CSIRO PUBLISHING
    University of Melbourne Author/s
    Li, Wenyi; Wade, John; Hossain, Mohammed; O'Brien-Simpson, Neil
    Affiliation
    Melbourne Dental School
    Florey Department of Neuroscience and Mental Health
    Metadata
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    Document Type
    Journal Article
    Citations
    Li, W., O'Brien-Simpson, N. M., Hossain, M. A. & Wade, J. D. (2020). The 9-Fluorenylmethoxycarbonyl (Fmoc) Group in Chemical Peptide Synthesis - Its Past, Present, and Future. AUSTRALIAN JOURNAL OF CHEMISTRY, 73 (4), pp.271-276. https://doi.org/10.1071/CH19427.
    Access Status
    Open Access
    URI
    http://hdl.handle.net/11343/252295
    DOI
    10.1071/CH19427
    Abstract
    <jats:p> The chemical formation of the peptide bond has long fascinated and challenged organic chemists. It requires not only the activation of the carboxyl group of an amino acid but also the protection of the Nα-amino group. The more than a century of continuous development of ever-improved protecting group chemistry has been married to dramatic advances in the chemical synthesis of peptides that, itself, was substantially enhanced by the development of solid-phase peptide synthesis by R. B. Merrifield in the 1960s. While the latter technology has continued to undergo further refinement and improvement in both its chemistry and automation, the development of the base-labile 9-fluorenylmethoxycarbonyl (Fmoc) group and its integration into current synthesis methods is considered a major landmark in the history of the chemical synthesis of peptides. The many beneficial attributes of the Fmoc group, which have yet to be surpassed by any other Nα-protecting group, allow very rapid and highly efficient synthesis of peptides, including ones of significant size and complexity, making it an even more valuable resource for research in the post-genomic world. This review charts the development and use of this Nα-protecting group and its adaptation to address the need for more green chemical peptide synthesis processes. </jats:p>

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