Solid-phase and solution-phase syntheses of oligomeric guanidines bearing peptide side chains |
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Authors: | Zhang Zhongsheng Fan Erkang |
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Affiliation: | Department of Biochemistry, Biomolecular Structure Center, University of Washington, Seattle, 98195, USA. |
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Abstract: | [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. |
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