Solid-phase and solution-phase syntheses of oligomeric guanidines bearing peptide side chains.
[reaction: see text] Synthetic strategies for preparing N,N'-bridged oligomeric guanidines bearing peptide side chains both on solid support and in solution are presented. Monomers are prepared from common alpha-amino acids and therefore contain conventionally protected peptide side chains. The side chains include alkyl, aromatic, hydroxyl, amino, carboxylic acid, and amide functional groups. Oligomer elongation utilizes acid-sensitive sulfonyl activated thiourea through the formation of carbodiimide intermediate. With proper preparation of monomers, synthesis of oligomer can be performed in two directions (equivalent to N to C terminal or C to N terminal in a peptide sequence) with excellent efficiency.
Zhang
Zhongsheng
Z
Department of Biochemistry, Biomolecular Structure Center, University of Washington, Seattle, 98195, USA.
Fan
Erkang
E
D002853:Chromatography, Liquid; D003500:Cyclization; D006146:Guanidines / Q000138:chemical synthesis / Q000737:chemistry*; D013058:Mass Spectrometry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D044367:Phase Transition; D012996:Solutions
D006146:Guanidines; D010455:Peptides; D012996:Solutions