title: Incorporation of chemoselective functionalities into peptoids via solid-phase submonomer synthesis.
abstract: 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.
authors.affiliation: Chiron Corporation, 4560 Horton Street, Emeryville, California 94608, USA. thomas_horn@chiron.com
authors.forename: Thomas
authors.initials: T
authors.lastname: Horn
authors.forename: Byoung-Chul
authors.initials: BC
authors.lastname: Lee
authors.forename: Ken A
authors.initials: KA
authors.lastname: Dill
authors.forename: Ronald N
authors.initials: RN
authors.lastname: Zuckermann
mesh_terms: D002851:Chromatography, High Pressure Liquid / Q000379:methods; D034444:Peptoids / Q000138:chemical synthesis*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
chemical_list: D034444:Peptoids