4.7 Article

Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization

Journal

CHEMICAL COMMUNICATIONS
Volume 49, Issue 4, Pages 385-387

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2cc36381j

Keywords

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Funding

  1. BASF of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  2. Covidien of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  3. Evonik of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  4. Firmenich of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  5. Novozymes of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  6. PepsiCo of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  7. Sherwin Williams of graduated NSF I/UCRC for Biocatalysis and Bioprocessing of Macromolecules at Polytechnic Institute of NYU
  8. Office Of The Director
  9. Office Of Internatl Science &Engineering [1243313] Funding Source: National Science Foundation

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A unique route to perfectly alternating oligopeptides is described. First, AG-OEt was prepared by standard chemical coupling. Then, AG-OEt was converted by papain-catalysis in 30 s to (AG)(x) (80%-yield, x = 9.4 +/- 0.3). Extension of this strategy to other alternating peptide compositions as well as the importance of selecting a protease and reaction conditions that avoid competing transamidation and hydrolysis reactions is discussed.

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