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

DOI PDF 被引用文献2件
  • Wenyi Li
    ABio21 Institute and Melbourne Dental School, University of Melbourne, Melbourne, Vic. 3010, Australia.
  • Neil M. O’Brien-Simpson
    ABio21 Institute and Melbourne Dental School, University of Melbourne, Melbourne, Vic. 3010, Australia.
  • Mohammed Akhter Hossain
    BFlorey Institute of Neuroscience and Mental Health, University of Melbourne, Melbourne, Vic. 3010, Australia.
  • John D. Wade
    BFlorey Institute of Neuroscience and Mental Health, University of Melbourne, Melbourne, Vic. 3010, Australia.

書誌事項

公開日
2019-11-22
権利情報
  • https://creativecommons.org/licenses/by-nc-nd/4.0/
DOI
  • 10.1071/ch19427
公開者
CSIRO Publishing

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説明

<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 Na-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 Na-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 Na-protecting group and its adaptation to address the need for more green chemical peptide synthesis processes.</jats:p>

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