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Malins LR, deGruyter JN, Robbins KJ, et al. Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products. J Am Chem Soc. 2017;139(14):5233-5241doi: 10.1021/jacs.7b01624.
Malins, L. R., deGruyter, J. N., Robbins, K. J., Scola, P. M., Eastgate, M. D., Ghadiri, M. R., & Baran, P. S. (2017). Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products. Journal of the American Chemical Society, 139(14), 5233-5241. https://doi.org/10.1021/jacs.7b01624
Malins, Lara R, et al. "Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products." Journal of the American Chemical Society vol. 139,14 (2017): 5233-5241. doi: https://doi.org/10.1021/jacs.7b01624
Malins LR, deGruyter JN, Robbins KJ, Scola PM, Eastgate MD, Ghadiri MR, Baran PS. Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products. J Am Chem Soc. 2017 Apr 12;139(14):5233-5241. doi: 10.1021/jacs.7b01624. Epub 2017 Mar 31. PMID: 28326777; PMCID: PMC5391502.
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J Am Chem Soc. 2017 Apr 12;139(14):5233-5241. doi: 10.1021/jacs.7b01624. Epub 2017 Mar 31.

Peptide Macrocyclization Inspired by Non-Ribosomal Imine Natural Products.

Journal of the American Chemical Society

Lara R Malins, Justine N deGruyter, Kevin J Robbins, Paul M Scola, Martin D Eastgate, M Reza Ghadiri, Phil S Baran

Affiliations

  1. Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
  2. Department of Discovery Chemistry, Bristol-Myers Squibb Research and Development , 5 Research Parkway, Wallingford, Connecticut 06492, United States.
  3. Chemical Development, Bristol-Myers Squibb , One Squibb Drive, New Brunswick, New Jersey 08903, United States.

PMID: 28326777 PMCID: PMC5391502 DOI: 10.1021/jacs.7b01624

Abstract

A thermodynamic approach to peptide macrocyclization inspired by the cyclization of non-ribosomal peptide aldehydes is presented. The method provides access to structurally diverse macrocycles by exploiting the reactivity of transient macrocyclic peptide imines toward inter- and intramolecular nucleophiles. Reactions are performed in aqueous media, in the absence of side chain protecting groups, and are tolerant of all proteinogenic functional groups. Macrocyclic products bearing non-native and rigidifying structural motifs, isotopic labels, and a variety of bioorthogonal handles are prepared, along with analogues of four distinct natural products. Structural interrogation of the linear and macrocyclic peptides using variable-temperature NMR and circular dichroism suggests that preorganization of linear substrates is not a prerequisite for macrocyclization.

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