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Article
Efficient photochemical synthesis of peptide-α-phenylthioesters
ChemBioChem: A European Journal of Cemical Biology, Synthetic Biology and Bio-nanotechnology
  • Andrew Pardo, University of Texas at El Paso
  • Tyrone J. Hogenauer, University of Texas at El Paso
  • Zhefeng Cai, University of Texas at El Paso
  • Julian A. Vellucci, University of Texas at El Paso
  • Efrain M. Castillo, University of Texas at El Paso
  • Carl W. Dirk, University of Texas at El Paso
  • Andreas H. Franz, University of the Pacific
  • Katja Michael, University of Texas at El Paso
Document Type
Article
Department
Chemistry
DOI
10.1002/cbic.201500266
Publication Date
9-7-2015
Disciplines
Abstract
Low yields and substantial epimerization of peptide-α-thioesters often compromise the overall efficiency of native chemical ligation (NCL). Peptide arylthioesters are more reactive than peptide alkylthioesters in NCL, but are also more difficult to handle due to their propensity to hydrolyze, and are therefore often generated in situ. However, pre-prepared peptide arylthioesters are required for some NCL applications. Here we present a 7-nitroindoline-based photochemical method that generates protected peptide phenylthioesters under neutral reaction conditions via their activated esters from photoreactive peptide precursors in high isolated yields, and with low levels of epimerization. This method is fully compatible with Fmoc-strategy solid-phase peptide synthesis. Global deprotection with trifluoroacetic acid furnishes peptide phenylthioesters for NCL. Photoreactive peptide precursors can also be converted into their hydrazides in two steps by this method.
Citation Information
Andrew Pardo, Tyrone J. Hogenauer, Zhefeng Cai, Julian A. Vellucci, et al.. "Efficient photochemical synthesis of peptide-α-phenylthioesters" ChemBioChem: A European Journal of Cemical Biology, Synthetic Biology and Bio-nanotechnology Vol. 16 Iss. 13 (2015) p. 1884 - 1889 ISSN: 0352-9568
Available at: http://works.bepress.com/andreas-franz/126/