Solid-phase synthesis of oligourea peptidomimetics employing the Fmoc protection strategy.
A solid-phase-Fmoc-based-synthesis strategy is described for oligourea peptidomimetics as well as a convenient general synthesis approach for the preparation of the required building blocks 5a-j and 5k. These are suitable for use in peptide or robot synthesizers, which is illustrated by the synthesis of oligourea peptidomimetics of part of Leu-enkephalin (10) and a neurotensin derivative (17).
Boeijen
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Department of Medicinal Chemistry, Utrecht Institute for Pharmaceutical Sciences, Utrecht University, P.O. Box 80082, NL-3508 TB Utrecht, The Netherlands.
van Ameijde
J
J
Liskamp
R M
RM
D000596:Amino Acids / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004743:Enkephalin, Leucine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D005449:Fluorenes / Q000737:chemistry*; D007202:Indicators and Reagents; D018716:Molecular Mimicry; D009496:Neurotensin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D009842:Oligopeptides / Q000138:chemical synthesis*; D011108:Polymers; D014508:Urea / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D000605:Amino Alcohols; D005449:Fluorenes; D007202:Indicators and Reagents; D009842:Oligopeptides; D011108:Polymers; D009496:Neurotensin; D004743:Enkephalin, Leucine; D014508:Urea; C054007:1-(9-fluorenyl)methyl chloroformate