ISSN:
1573-3904
Keywords:
Acylation
;
Sulfonamides
;
Libraries
;
Combinatorial chemistry
;
Intramolecular cyclization
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Summary 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 produre a peptide library consisting of unnatural amino acids, three amino acids were prepared by acylation/sulfonation of the δ-amino function of ornithine and they were incorporated in a random sequence. Depending upon the acidity of the remaining proton on the δ-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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00119154
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