PDF herunterladen
Synlett 1999; 1999(S1): 963-965
DOI: 10.1055/s-1999-3178
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Coupling Reagent Dependent Regioselectivity in the Synthesis of Lysine Dipeptides

Shimon Shatzmiller* , Pat N. Confalone, Ariela Abiri
  • *The Beverly and Raymond Sackler Faculty of Exact Sciences, School of Chemistry, Tel-Aviv University, Ramat-Aviv, Tel-Aviv 69978, Israel; Fax 9 72-3-6 40 92 92; E-mail: shatzi@post.tau.ac.il
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 1999 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Participation of either the Nℇ or Nα of l-methyl lysinate (2) in peptide bond formation could be selectively achieved by the use of either isobutyl chloroformate (method A) or N,N-bis(2-oxo-3-oxazolidinyl) phosphinic chloride (BOP-Cl) (method B), respectively. The amidation performed according to method A gives high yields of the dipeptides 3a-e, irrespective of the amino acids used. In method B, Nα amidation is highly preferred especially with bulky amino acids, yielding 4a, 4c and 4e. The less bulky 4b and 4d gave 4.5 and 20 regioselection Nα/Nℇ amidation ratios. A mechanistical rationalization for these selectivities is discussed.

Nα or Nℇ peptide bond formation