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Synthesis of N alpha-(1-phenyl-2-mercaptoethyl) amino acids, new building blocks for ligation and cyclization at non-cysteine sites: scope and limitations in peptide synthesis

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Published in Journal of Organic Chemistry. 2004, vol. 69, no. 26, p. 9208-14
Abstract A new and convenient method for the synthesis and incorporation of N(alpha)-(1-phenyl-2-mercaptoethyl)-derivatized amino acids applicable to chemical ligation at non-cysteine sites is presented. N(alpha)-Auxiliary derivatives of glycine and alanine were easily prepared using reductive amination approaches. Several strategies for the incorporation of these derivatives into peptide chains were investigated: coupling without protection, with acid-labile protection, with base-labile protection, and via a novel protection strategy using the thiazolidine derivative. All amino acid derivatives were successfully coupled to various peptide resins, and with the exception of those incorporating Boc-protected derivatives, all resins yielded the desired peptide fragments. However, the coupling of the two alanine derivative diastereomers generated some epimerization. Finally, N-terminal auxiliary glycine and alanine peptides were cyclized, and the corresponding native circular peptides were obtained upon successful removal of the auxiliary.
Keywords Amino Acids/chemistryCysteine/chemistryMagnetic Resonance SpectroscopyMass SpectrometryPeptides/chemical synthesis
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PMID: 15609957
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Research group HIV (835)
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TCHERTCHIAN, Sylvie, HARTLEY, Oliver, BOTTI, Paolo. Synthesis of N alpha-(1-phenyl-2-mercaptoethyl) amino acids, new building blocks for ligation and cyclization at non-cysteine sites: scope and limitations in peptide synthesis. In: Journal of Organic Chemistry, 2004, vol. 69, n° 26, p. 9208-14. https://archive-ouverte.unige.ch/unige:26046

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Deposited on : 2013-01-30

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