title: Solid-phase synthesis of amino- and carboxyl-functionalized unnatural alpha-amino acid amides.
abstract: A new solid-phase synthesis efficiently incorporates three different substituents (from R(1)-X, R(2)-CO(2)H, and R(3)-NH(2)) into a glycine-based peptidomimetic scaffold. The synthetic sequence is general and is typically accomplished in >50% overall isolated yield. Alkylating agents with a range of reactivities and normal and branched primary amines give good results. Utility was demonstrated by the synthesis of a series of protected phosphotyrosine mimetics.
authors.affiliation: Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, Indiana 46202-3274, USA. wscott@iupui.edu
authors.forename: William L
authors.initials: WL
authors.lastname: Scott
authors.forename: Ziniu
authors.initials: Z
authors.lastname: Zhou
authors.forename: Jacek G
authors.initials: JG
authors.lastname: Martynow
authors.forename: Martin J
authors.initials: MJ
authors.lastname: O'Donnell
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D005998:Glycine / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D005998:Glycine