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Epimerization-Free C-Terminal Peptide Activation

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Abstract

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Smooth operation: C-terminal peptide activation with full stereointegrity was accomplished using a copper(II)-mediated coupling reaction of carboxylic acids with arylboroxines (see scheme, NCL = native chemical ligation, Boc = tert-butoxycarbonyl). This method allows epimerization-free activation and ligation of peptides with racemization-prone phenylglycine at the C terminus.

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DOI

10.1002/chem.201303347

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Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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Keywords

  • aminolysis;
  • aryl esterification;
  • copper;
  • peptide activation;
  • peptides

Publication History

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  • Manuscript Received:

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  • The National Research School Combination Catalysis

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  1. 1Stanimir Popovic, Linda Wijsman, Iris R. Landman, Maaike F. Sangster, Dorien Pastoors, Berend B. Veldhorst, Henk Hiemstra, Jan H. van Maarseveen, Fine-Tuning the Balance between Peptide Thioester Cyclization and Racemization, European Journal of Organic Chemistry, 2016, 2016, 3, 443Wiley Online Library
  2. 2Jakov Ivkovic, Christian Lembacher-Fadum, Rolf Breinbauer, A rapid and efficient one-pot method for the reduction of N-protected α-amino acids to chiral α-amino aldehydes using CDI/DIBAL-H, Org. Biomol. Chem., 2015, 13, 42, 10456CrossRef
  3. 3Clare E. Jacobson, Noelia Martinez-Muñoz, David J. Gorin, Aerobic Copper-Catalyzed O-Methylation with Methylboronic Acid, The Journal of Organic Chemistry, 2015, 80, 14, 7305CrossRef
  4. 4Arjen C. Breman, Suze E. M. Telderman, Roy P. M. van Santen, Jamie I. Scott, Jan H. van Maarseveen, Steen Ingemann, Henk Hiemstra, CinchonaAlkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines, The Journal of Organic Chemistry, 2015, 80, 21, 10561CrossRef
  5. 5Chun Ling Tung, Clarence T. T. Wong, Xuechen Li, Peptide 2-formylthiophenol esters do not proceed through a Ser/Thr ligation pathway, but participate in a peptide aminolysis to enable peptide condensation and cyclization, Org. Biomol. Chem., 2015, 13, 25, 6922CrossRef