Abstract
We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing α-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5002-5005 |
| Number of pages | 4 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 21 |
| Issue number | 17 |
| DOIs | |
| State | Published - Sep 1 2011 |
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Keywords
- Aptamer
- Covalent tethering
- Helix-threading peptide
- Nucleoside analog
- Templated reaction
ASJC Scopus subject areas
- Pharmaceutical Science
- Drug Discovery
- Organic Chemistry
- Molecular Medicine
- Molecular Biology
- Clinical Biochemistry
- Biochemistry
Cite this
Covalent stabilization of a small molecule-RNA complex. / Peacock, Hayden; Bachu, Radhika; Beal, Peter A.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 21, No. 17, 01.09.2011, p. 5002-5005.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Covalent stabilization of a small molecule-RNA complex
AU - Peacock, Hayden
AU - Bachu, Radhika
AU - Beal, Peter A.
PY - 2011/9/1
Y1 - 2011/9/1
N2 - We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing α-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies.
AB - We demonstrate covalent bond formation between an RNA aptamer containing a cysteamine-tethered nucleobase and helix-threading peptides (HTPs) containing α-bromoacetamide N-termini. The reaction is high yielding and inhibited by a DNA strand Watson-Crick complementary to the aptamer sequence indicating covalent reaction is dependent on the high affinity HTP-binding site present in the folded aptamer. These results are important for future structural studies of HTP-RNA complexes and methods for the discovery of new high affinity analogs via covalent tethering strategies.
KW - Aptamer
KW - Covalent tethering
KW - Helix-threading peptide
KW - Nucleoside analog
KW - Templated reaction
UR - http://www.scopus.com/inward/record.url?scp=80051795315&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=80051795315&partnerID=8YFLogxK
U2 - 10.1016/j.bmcl.2011.04.136
DO - 10.1016/j.bmcl.2011.04.136
M3 - Article
C2 - 21601451
AN - SCOPUS:80051795315
VL - 21
SP - 5002
EP - 5005
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 17
ER -