Solid-phase synthesis of amino- and carboxyl-functionalized unnatural alpha-amino acid amides.
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.
Scott
William L
WL
Department of Chemistry and Chemical Biology, Indiana University Purdue University Indianapolis, Indianapolis, Indiana 46202-3274, USA. wscott@iupui.edu
Zhou
Ziniu
Z
Martynow
Jacek G
JG
O'Donnell
Martin J
MJ
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
D000577:Amides; D000596:Amino Acids; D005998:Glycine