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Amino acids derived from ornithine

✍ Scribed by Theo Lescrinier; Christophe Pannecouque; Jef Rozenski; Arthur Aerschot; Piet Herdewijn

Publisher: Springer Netherlands
Year: 1995
Tongue: English
Weight: 175 KB
Volume: 2
Category: Article
ISSN: 1573-3149
DOI: 10.1007/bf00119154

No coin nor oath required. For personal study only.

✦ Synopsis

The use of copper complexes in the protection of lysine and tyrosine side chains has been extensively described. Based on this work and in order to produce a peptide library consisting of unnatural amino acids, three amino acids were prepared by acylation/sulfonation of the ~i-amino function of ornithine and they were incorporated in a random sequence. Depending upon the acidity of the remaining proton on the g-nitrogen, an intramolecular cyclization competed with the amide formation using standard coupling conditions (DIC/HOBt/DIEA). This side reaction could be suppressed by simple removal of the base from the condensation mixture. The obtained peptides were purified on a PLRP-s ® column and their identity was confirmed by mass spectrometry.

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