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Facile Solid-Phase Parallel Synthesis of Linear and Cyclic Peptoids for Comparative Studies of Biological Activity

Title
Facile Solid-Phase Parallel Synthesis of Linear and Cyclic Peptoids for Comparative Studies of Biological Activity
Authors
Park, ShinaeKwon, Yong-Uk
Ewha Authors
권용억
SCOPUS Author ID
권용억scopus
Issue Date
2015
Journal Title
ACS COMBINATORIAL SCIENCE
ISSN
2156-8952JCR Link2156-8944JCR Link
Citation
vol. 17, no. 3, pp. 196 - 201
Keywords
cyclic peptoidsmacrocyclizationmactolactionizationpeptoid synthesis
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS
Abstract
A series of linear and cyclic peptoids, which were expected to possess better pharmacokinetic properties and biological activities for blocking the interaction between apolipoprotein E and amyloid-beta, were designed and synthesized as possible therapeutic agents. Peptoids were easily synthesized on solid-phase by the submonomer strategy and polar side chain-containing amines were effectively introduced under the modified reaction conditions. For the synthesis of cyclic peptoids, beta-alanine protected with the 2-phenylisopropyl group, which could be selectively removed by 2% TFA, was used as a primary amine to afford a complete peptoid unit. The macrolactamization between the carboxylic acid of beta-alanine moiety and terminal amine of peptoids was successfully performed in the presence of the PyAOP coupling agent on solid-phase in all the cases, providing various sizes of cyclic peptoids. In particular, some cyclic peptoids prepared in this study are the largest in size among cyclic peptoids reported to date. The synthetic strategy which was adopted in this study can also provide a robust platform for solid-phase construction of cyclic peptoid libraries. Currently, synthetic peptoids have been used to test interesting biological activities including the ApoE/A beta interaction inhibition, nontoxicity, the blood-brain barrier permeability, etc.
DOI
10.1021/co5001647
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자연과학대학 > 화학·나노과학전공 > Journal papers
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