TY  - JOUR
A1  - Danneberg, Friederike
A1  - Westemeier, Hauke
A1  - Horx, Philip
A1  - Zellmann, Felix
A1  - Dörr, Kathrin
A1  - Kalden, Elisabeth
A1  - Zeiger, Mirco
A1  - Akpinar, Abdullah
A1  - Berger, Robert
A1  - Göbel, Michael
T1  - RNA hydrolysis by heterocyclic amidines and guanidines: parameters affecting reactivity
T2  - European journal of organic chemistry
N2  - 2-Aminobenzimidazole 10, although a weak catalyst in the monomeric state, is a successful building block for effective artificial ribonucleases. In an effort to identify new building blocks with improved catalytic potential, RNA cleavage by a variety of heterocyclic amidines and guanidines has been studied. In addition to pKa values and steric effects, the energy difference between tautomeric forms seems to be another important parameter for catalysis. This information is available from quantum chemical calculations on higher levels, but semiempirical methods are sufficient to get a first estimate. According to this assumption, imidazoimidazol 18, characterized by isoenergetic tautomeric forms, is superior to 2-aminoimidazol 6, the best candidate among the simple compounds. By far the largest effects are seen with 2-aminoperimidine 24, which rapidly cleaves RNA even in the micromolar concentration range. The impressive reactivity, however, is related to a tendency of compound 24 to form polycationic aggregates which are the actual catalysts.
KW  - Ab initio calculations
KW  - Catalysis
KW  - Post-Hartree-Fock methods
KW  - RNA cleavage
KW  - Semi-empiricalcalculations
Y1  - 2021
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/63895
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-638953
SN  - 1434-193X
N1  - Open Access funding enabled and organized by Projekt DEAL.
VL  - 2021
IS  - 46 = Special Issue: In Memory of Klaus Hafner
SP  - 6358
EP  - 6366
PB  - Wiley VCZ
CY  - Weinheim
ER  -