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Peptidosteroid Tweezers Revisited: DNA Binding Through an Optimised Design
Author(s) -
Carrette Lieselot L. G.,
Morii Takashi,
Madder Annemieke
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301854
Subject(s) - chemistry , peptide , dna , combinatorial chemistry , amphiphile , scaffold , tweezers , self assembly , nanotechnology , biophysics , biochemistry , organic chemistry , polymer , medicine , materials science , biomedical engineering , copolymer , biology
A dipodal peptidosteroid based on a deoxycholic acid scaffold was designed as a transcription factor model to study, and ultimately interfere in, selective protein–DNA interactions. In this paper, the selective binding of such a dipodal peptidosteroid to its DNA binding site is described for the first time, thus proving the concept and confirming the potential of the design. To achieve this, two 25‐mer peptides were synthesized in parallel and in close proximity on a rigid amphiphilic scaffold, attached by flexible linkers. Peptide aggregation complicated the synthesis under conventional conditions to such an extent that optimization and the use of microwave assistance were required for a successful synthesis. As such, this synthesis is a good model to showcase the beneficial effects of microwave assistance in peptide synthesis.