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Synthesis 1996; 1996(11): 1277-1279
DOI: 10.1055/s-1996-4387
short paper
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A New Method for the Synthesis of (S)-α-Methylisoserine and Its Incorporation into Peptides

Raul Pires, Klaus Burger*
  • *Institut für Organische Chemie der Universität Leipzig, Talstraße 35, D-04103 Leipzig, Germany, Fax +49(341)9736599
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Publikationsdatum:
31. Dezember 2000 (online)

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(S)-(+)-Citramalic acid is converted into isocyanate 4 using hexafluoroacetone as the protecting agent. Isocyanate 4 represents a doubly activated species, which upon reaction with alcohols provides N-protected, carboxyl-activated α-methylisoserine derivatives, perfectly suited for peptide synthesis (5 → 8). Acylation of 4 with N-protected amino acids gives fully protected carboxyl-activated dipeptides. Ring opening with amino acid esters results in the formation of tripeptides (9 → 10).

non-proteinogenic amino acids - peptides - (S)-(+)-citramalic acid - (S)-α-methylisoserine - hexafluoroacetone