Abstract
Canonical peptide nucleic acid (PNA), in which naturally occurring nucleobases (A, G, C, and T) are bound to a poly-(N-(2-aminoethyl)glycine) backbone, forms a stable duplex with single-stranded complementary DNA. However, this PNA hardly forms stable complexes with double-stranded DNA. We here show that, when some of the A and T groups therein are replaced with pseudo-complementary nucleobases (2,6-diaminopurine and 2-thiouracil), even only one strand of this partially pseudo-complementary PNA efficiently invades double-stranded DNA. This single-strand invasion spontaneously occurs at 25-50°C, indicating its promising applicability to versatile purposes both in vivo and in vitro. The promotion by 2,6-diaminopurine is primarily attributed to the formation of an additional hydrogen bond with T in one of the two DNA strands, whereas the 2-S atom in 2-thiouracil promotes stacking interactions with adjacent nucleobases. Furthermore, the present new methodology is successfully employed to site-selective scission of double-stranded DNA, in which the single-stranded portion, formed upon the single-strand invasion, is preferentially hydrolyzed by Ce IV /EDTA complex.
| Original language | English |
|---|---|
| Pages (from-to) | 330-335 |
| Number of pages | 6 |
| Journal | Bulletin of the Chemical Society of Japan |
| DOIs | |
| Publication status | Published - 2019 Jan 1 |
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Keywords
- Invasion
- PNA
- Pseudo-complementary
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Promotion of single-strand invasion of PNA to double-stranded DNA by pseudo-complementary base pairing. / Shigi, Narumi; Mizuno, Yuki; Kunifuda, Hiroko; Matsumura, Kazunari; Komiyama, Makoto.
In: Bulletin of the Chemical Society of Japan, 01.01.2019, p. 330-335.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Promotion of single-strand invasion of PNA to double-stranded DNA by pseudo-complementary base pairing
AU - Shigi, Narumi
AU - Mizuno, Yuki
AU - Kunifuda, Hiroko
AU - Matsumura, Kazunari
AU - Komiyama, Makoto
PY - 2019/1/1
Y1 - 2019/1/1
N2 - Canonical peptide nucleic acid (PNA), in which naturally occurring nucleobases (A, G, C, and T) are bound to a poly-(N-(2-aminoethyl)glycine) backbone, forms a stable duplex with single-stranded complementary DNA. However, this PNA hardly forms stable complexes with double-stranded DNA. We here show that, when some of the A and T groups therein are replaced with pseudo-complementary nucleobases (2,6-diaminopurine and 2-thiouracil), even only one strand of this partially pseudo-complementary PNA efficiently invades double-stranded DNA. This single-strand invasion spontaneously occurs at 25-50°C, indicating its promising applicability to versatile purposes both in vivo and in vitro. The promotion by 2,6-diaminopurine is primarily attributed to the formation of an additional hydrogen bond with T in one of the two DNA strands, whereas the 2-S atom in 2-thiouracil promotes stacking interactions with adjacent nucleobases. Furthermore, the present new methodology is successfully employed to site-selective scission of double-stranded DNA, in which the single-stranded portion, formed upon the single-strand invasion, is preferentially hydrolyzed by Ce IV /EDTA complex.
AB - Canonical peptide nucleic acid (PNA), in which naturally occurring nucleobases (A, G, C, and T) are bound to a poly-(N-(2-aminoethyl)glycine) backbone, forms a stable duplex with single-stranded complementary DNA. However, this PNA hardly forms stable complexes with double-stranded DNA. We here show that, when some of the A and T groups therein are replaced with pseudo-complementary nucleobases (2,6-diaminopurine and 2-thiouracil), even only one strand of this partially pseudo-complementary PNA efficiently invades double-stranded DNA. This single-strand invasion spontaneously occurs at 25-50°C, indicating its promising applicability to versatile purposes both in vivo and in vitro. The promotion by 2,6-diaminopurine is primarily attributed to the formation of an additional hydrogen bond with T in one of the two DNA strands, whereas the 2-S atom in 2-thiouracil promotes stacking interactions with adjacent nucleobases. Furthermore, the present new methodology is successfully employed to site-selective scission of double-stranded DNA, in which the single-stranded portion, formed upon the single-strand invasion, is preferentially hydrolyzed by Ce IV /EDTA complex.
KW - Invasion
KW - PNA
KW - Pseudo-complementary
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UR - http://www.scopus.com/inward/citedby.url?scp=85061792762&partnerID=8YFLogxK
U2 - 10.1246/bcsj.20180211
DO - 10.1246/bcsj.20180211
M3 - Article
SP - 330
EP - 335
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
ER -