化学
氨基酸
组合化学
碱基
肽
肽合成
环加成
立体化学
催化作用
有机化学
DNA
生物化学
作者
Rolf A. Kramer,Konrad H. Bleicher,Helma Wennemers
标识
DOI:10.1002/hlca.201200557
摘要
Abstract A straightforward synthesis of orthogonally protected nucleoproline (Nup) amino acids and their coupling to oligomers are described. A key step is the attachment of alkynylated nucleobases to Fmoc‐protected 4‐azidoproline (Fmoc‐Azp‐OH) by a Cu‐catalyzed 1,3‐dipolar cycloaddition (‘click reaction’). The developed protocol allows preparation of the nucleoprolines in scales of >30 g. Solid‐phase peptide synthesis proved to be straightforward with these Nup amino acids. The resulting oligonucleoproline peptides adopt defined helices, are very well H 2 O soluble, and show comparable cell‐penetrating properties as recently reported α ‐nucleoalanine peptides.
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