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RNA Cleavage Catalyzed by Amphoteric Bis(acyl)guanidinium Derivatives
Author(s) -
Göbel Michael W.,
Roussev Christo D.,
Scheffer Ute
Publication year - 2014
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300308
Subject(s) - chemistry , catalysis , cleavage (geology) , rna , hydrolysis , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , gene , geotechnical engineering , fracture (geology) , engineering
Described herein are two series (twelve compounds each) of very closely related guanidinium‐based receptors and their ability to catalyze hydrolytic cleavage of a unique RNA substrate – oligo‐dT flanked t rans ‐ A ctivation R esponsive region of the HIV‐1 mRNA, TAR RNA. The significant difference in activities of otherwise very similar compounds is discussed, and direct and indirect evidences supporting our interpretation are presented. The results indicate that improvements in catalytic efficiency could be achieved with little modification of the structure of a relatively weak catalyst, and that a crucial feature could be a finely calibrated interplay between anion‐binding and proton‐donating abilities.