Synthesis of γ-substituted peptide nucleic acids: A new place to attach fluorophores without affecting DNA binding

被引：72

作者：

Englund, EA

Appella, DH ^{[1
]}

机构：

[1] NIDDK, Bioorgan Chem Lab, NIH, DHHS, Bethesda, MD 20892 USA

[2] Northwestern Univ, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 16期

关键词：

D O I：

10.1021/ol051143z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Molecular beacon strategies using PNA are currently restricted to fluorophore attachment to the ends of the PNA. We report the synthesis of PNA oligomers wherein fluorophores can be attached to the PNA backbone from novel gamma-lysine PNA monomers. Oligomers incorporating the modified PNA showed comparable thermal stability to the corresponding aegPNA oligomer with DNA. When the modified PNA oligomer was annealed with complementary DNA, the fluorescence intensity increased 4-fold over the unbound PNA.

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页码：3465 / 3467

页数：3

相关论文

共 17 条

[1] PEPTIDE NUCLEIC-ACID (PNA) WITH A CHIRAL BACKBONE BASED ON ALANINE [J].

DUEHOLM, KL ;

PETERSEN, KH ;

JENSEN, DK ;

EGHOLM, M ;

NIELSEN, PE ;

BUCHARDT, O .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (08) :1077-1080

[2] Solution structure of a peptide nucleic acid DNA duplex [J].

Eriksson, M ;

Nielsen, PE .

NATURE STRUCTURAL BIOLOGY, 1996, 3 (05) :410-413

[3]

Haaima G, 1996, ANGEW CHEM INT EDIT, V35, P1939

[4] A highly discriminating quencher-free molecular beacon for probing DNA [J].

Hwang, GT ;

Seo, YJ ;

Kim, BH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6528-6529

[5] STRUCTURE-ACTIVITY STUDIES OF THE BINDING OF MODIFIED PEPTIDE NUCLEIC-ACIDS (PNAS) TO DNA [J].

HYRUP, B ;

EGHOLM, M ;

NIELSEN, PE ;

WITTUNG, P ;

NORDEN, B ;

BUCHARDT, O .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :7964-7970

[6] Hybridization of DNA and PNA molecular beacons to single-stranded and double-stranded DNA targets [J].

Kuhn, H ;

Demidov, VV ;

Coull, JM ;

Fiandaca, MJ ;

Gildea, BD ;

Frank-Kamenetskii, MD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) :1097-1103

[7] SYNTHESIS AND PROPERTIES OF AN OLIGODEOXYNUCLEOTIDE MODIFIED WITH A PYRENE DERIVATIVE AT THE 5'-PHOSPHATE [J].

MANN, JS ;

SHIBATA, Y ;

MEEHAN, T .

BIOCONJUGATE CHEMISTRY, 1992, 3 (06) :554-558

[8] SEQUENCE-SELECTIVE RECOGNITION OF DNA BY STRAND DISPLACEMENT WITH A THYMINE-SUBSTITUTED POLYAMIDE [J].

NIELSEN, PE ;

EGHOLM, M ;

BERG, RH ;

BUCHARDT, O .

SCIENCE, 1991, 254 (5037) :1497-1500

[9] Imaging gene expression using oligonucleotides and peptide nucleic acids [J].

Paroo, Z ;

Corey, DR .

JOURNAL OF CELLULAR BIOCHEMISTRY, 2003, 90 (03) :437-442

[10] Short PNA molecular beacons for real-time PCR allelic discrimination of single nucleotide polymorphisms [J].

Petersen, K ;

Vogel, U ;

Rockenbauer, E ;

Nielsen, KV ;

Kolvraa, S ;

Bolund, L ;

Nexo, B .

MOLECULAR AND CELLULAR PROBES, 2004, 18 (02) :117-122