Incorporation of chemoselective functionalities into peptoids via solid-phase submonomer synthesis.
A simple route to the introduction of a number of chemoselective functional groups into peptoids (oligo(N-substituted glycines)) by an extension of the standard solid-phase submonomer method is reported. The following groups were introduced: aminooxyacetamide, N-(carbamoylmethyl)acetohydrazide, mercaptoacetamide, 2-pyridinesulfenylmercaptoacetamide, and aldehyde-terminated peptoids. The method uses commercially available reagents, is fully compatible with standard peptoid submonomer synthesis conditions, is easily automated, and generates the desired functionalized peptoid in high yield and purity. Peptoids with suitable pairs of chemoselective ligation groups were joined in high yield.
Horn
Thomas
T
Chiron Corporation, 4560 Horton Street, Emeryville, California 94608, USA. thomas_horn@chiron.com
Lee
Byoung-Chul
BC
Dill
Ken A
KA
Zuckermann
Ronald N
RN
D002851:Chromatography, High Pressure Liquid / Q000379:methods; D034444:Peptoids / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D034444:Peptoids