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Letters in Peptide Science

, Volume 5, Issue 2–3, pp 129–131 | Cite as

Influence of proline and β-turn mimetics on the cyclization of penta- and hexapeptides

  • Jana Klose
  • Angelika Ehrlich
  • Michael Bienert
Article

Summary

Proline and Pro-derived peptidomimetics, such as meoxPro-Oic (4-methoxy-proline-octahydro indolic acid), and DBF (2-aminoethyl-6-dibenzofuran propionic acid) were introduced into thymopentin-derived penta-[SP5-] and hexa-[SP6-] peptides and penta-, hexa- and hepta-alanine. Surprisingly, we found that cyclomonomer formation in the investigated penta- and hexapeptides was drastically hindered by the presence of proline regardless of position.

Key words

all-l-peptides DBF meoxPro-Oic turn-induction 

Abbreviations

DIEA

diisopropylethylamine

DMF

dimethylformamide

ES-MS

electrospray ionization mass spectrometry

HOAt

1-hydroxy-7-azabenzotriazole

HAPyU

(7-azabenzotriazol-1-yl)-1,1,3,3-bis(tetramethylene)-uronium hexafluorophosphate

Hmb

2-hydroxy-4-methoxybenzyl

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Copyright information

© Kluwer Academic Publishers 1998

Authors and Affiliations

  • Jana Klose
    • 1
  • Angelika Ehrlich
    • 1
  • Michael Bienert
    • 1
  1. 1.Institute of Molecular PharmacologyBerlinGermany

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