Details
| Original language | English |
|---|---|
| Pages (from-to) | 8421-8438 |
| Number of pages | 18 |
| Journal | TETRAHEDRON |
| Volume | 53 |
| Issue number | 25 |
| Publication status | Published - 23 Jun 1997 |
Abstract
An RNAse active site model system is described. The rigid steroid backbone is used as the template on which guanidinium and imidazole moieties, necessary for the transesterification/cleavage. are assembled. By changing the stereochemistry at C11 of 2, and varying the guanidinium side chains, active compounds 9, 11, 13, 15 with different hydrolytic behavior are obtained. Comparison of the steroid compounds clearly demonstrates that changes in the geometry can influence the cleavage reaction of RNA analogs. Furthermore, an intramolecular base can enhance the cleavage rate. The pK(a) values of the most active bis(guanidinium) compound 3 has been determined and the pH dependence of the cleavage reaction is discussed.
ASJC Scopus subject areas
- Biochemistry, Genetics and Molecular Biology(all)
- Biochemistry
- Pharmacology, Toxicology and Pharmaceutics(all)
- Drug Discovery
- Chemistry(all)
- Organic Chemistry
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In: TETRAHEDRON, Vol. 53, No. 25, 23.06.1997, p. 8421-8438.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of RNAse active site model systems using a steroid template
AU - Oost, Thorsten
AU - Kalesse, Markus
PY - 1997/6/23
Y1 - 1997/6/23
N2 - An RNAse active site model system is described. The rigid steroid backbone is used as the template on which guanidinium and imidazole moieties, necessary for the transesterification/cleavage. are assembled. By changing the stereochemistry at C11 of 2, and varying the guanidinium side chains, active compounds 9, 11, 13, 15 with different hydrolytic behavior are obtained. Comparison of the steroid compounds clearly demonstrates that changes in the geometry can influence the cleavage reaction of RNA analogs. Furthermore, an intramolecular base can enhance the cleavage rate. The pK(a) values of the most active bis(guanidinium) compound 3 has been determined and the pH dependence of the cleavage reaction is discussed.
AB - An RNAse active site model system is described. The rigid steroid backbone is used as the template on which guanidinium and imidazole moieties, necessary for the transesterification/cleavage. are assembled. By changing the stereochemistry at C11 of 2, and varying the guanidinium side chains, active compounds 9, 11, 13, 15 with different hydrolytic behavior are obtained. Comparison of the steroid compounds clearly demonstrates that changes in the geometry can influence the cleavage reaction of RNA analogs. Furthermore, an intramolecular base can enhance the cleavage rate. The pK(a) values of the most active bis(guanidinium) compound 3 has been determined and the pH dependence of the cleavage reaction is discussed.
UR - http://www.scopus.com/inward/record.url?scp=0031007572&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00526-7
DO - 10.1016/S0040-4020(97)00526-7
M3 - Article
AN - SCOPUS:0031007572
VL - 53
SP - 8421
EP - 8438
JO - TETRAHEDRON
JF - TETRAHEDRON
SN - 0040-4020
IS - 25
ER -