Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine

G Haaima; O Dahl; Peter E. Nielsen

Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine

Transcription, RNA, and Gene Medicine Program

Abstract

The synthesis of a diaminopurine PNA monomer, N-[N6-(benzyloxycarbonyl)-2,6-diaminopurine-9-yl] acetyl-N-(2-t-butyloxycarbonylaminoethyl)glycine, and the incorporation of this monomer into PNA oligomers are described. Substitution of adenine by diaminopurine in PNA oligomers increased the T m of duplexes formed with complementary DNA, RNA or PNA by 2.5-6.5 degrees C per diaminopurine. Furthermore, discrimination against mismatches facing the diaminopurine in the hybridizing oligomer is improved. Finally, a homopurine decamer PNA containing six diaminopurines is shown to form a (gel shift) stable strand displacement complex with a target in a 246 bp double-stranded DNA fragment.

Original language	English
Journal	Nucleic Acids Research
Volume	25
Issue number	22
Pages (from-to)	4639-43
Number of pages	5
ISSN	0305-1048
Publication status	Published - 15 Nov 1997

Keywords

2-Aminopurine/analogs & derivatives
Adenine
DNA/metabolism
Molecular Mimicry
Nucleic Acids/chemical synthesis
Nylons/chemical synthesis
Peptides/chemistry

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@article{f1b46d6d1d594e89bec6aa2092283056,

title = "Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine",

abstract = "The synthesis of a diaminopurine PNA monomer, N-[N6-(benzyloxycarbonyl)-2,6-diaminopurine-9-yl] acetyl-N-(2-t-butyloxycarbonylaminoethyl)glycine, and the incorporation of this monomer into PNA oligomers are described. Substitution of adenine by diaminopurine in PNA oligomers increased the T m of duplexes formed with complementary DNA, RNA or PNA by 2.5-6.5 degrees C per diaminopurine. Furthermore, discrimination against mismatches facing the diaminopurine in the hybridizing oligomer is improved. Finally, a homopurine decamer PNA containing six diaminopurines is shown to form a (gel shift) stable strand displacement complex with a target in a 246 bp double-stranded DNA fragment.",

keywords = "2-Aminopurine/analogs & derivatives, Adenine, DNA/metabolism, Molecular Mimicry, Nucleic Acids/chemical synthesis, Nylons/chemical synthesis, Peptides/chemistry",

author = "G Haaima and O Dahl and Nielsen, {Peter E.}",

year = "1997",

month = nov,

day = "15",

language = "English",

volume = "25",

pages = "4639--43",

journal = "Nucleic Acids Research",

issn = "0305-1048",

publisher = "Oxford University Press",

number = "22",

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TY - JOUR

T1 - Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine

AU - Haaima, G

AU - Dahl, O

AU - Nielsen, Peter E.

PY - 1997/11/15

Y1 - 1997/11/15

N2 - The synthesis of a diaminopurine PNA monomer, N-[N6-(benzyloxycarbonyl)-2,6-diaminopurine-9-yl] acetyl-N-(2-t-butyloxycarbonylaminoethyl)glycine, and the incorporation of this monomer into PNA oligomers are described. Substitution of adenine by diaminopurine in PNA oligomers increased the T m of duplexes formed with complementary DNA, RNA or PNA by 2.5-6.5 degrees C per diaminopurine. Furthermore, discrimination against mismatches facing the diaminopurine in the hybridizing oligomer is improved. Finally, a homopurine decamer PNA containing six diaminopurines is shown to form a (gel shift) stable strand displacement complex with a target in a 246 bp double-stranded DNA fragment.

AB - The synthesis of a diaminopurine PNA monomer, N-[N6-(benzyloxycarbonyl)-2,6-diaminopurine-9-yl] acetyl-N-(2-t-butyloxycarbonylaminoethyl)glycine, and the incorporation of this monomer into PNA oligomers are described. Substitution of adenine by diaminopurine in PNA oligomers increased the T m of duplexes formed with complementary DNA, RNA or PNA by 2.5-6.5 degrees C per diaminopurine. Furthermore, discrimination against mismatches facing the diaminopurine in the hybridizing oligomer is improved. Finally, a homopurine decamer PNA containing six diaminopurines is shown to form a (gel shift) stable strand displacement complex with a target in a 246 bp double-stranded DNA fragment.

KW - 2-Aminopurine/analogs & derivatives

KW - Adenine

KW - DNA/metabolism

KW - Molecular Mimicry

KW - Nucleic Acids/chemical synthesis

KW - Nylons/chemical synthesis

KW - Peptides/chemistry

M3 - Journal article

C2 - 9358176

SN - 0305-1048

VL - 25

SP - 4639

EP - 4643

JO - Nucleic Acids Research

JF - Nucleic Acids Research

IS - 22

ER -

Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine

Abstract

Keywords

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