γ-substituted peptide nucleic acids constructed from L-lysine are a versatile scaffold for multifunctional display

被引:90
作者
Englund, Ethan A.
Appella, Daniel H. [1 ]
机构
[1] NIDDK, Bioorgan Chem Lab, NIH, DHHS, Bethesda, MD 20892 USA
[2] NIDDK, NIH, DHHS, Bethesda, MD 20892 USA
[3] Northwestern Univ, Evanston, IL 60208 USA
关键词
binding studies; chiral backbone; DNA structures; nucleic acids; peptide nucleic acids;
D O I
10.1002/anie.200603483
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Figure Presented) On display: This model shows DNA (pink) annealed to a peptide nucleic acid (PNA; orange) containing several L-lysine γ side chains (LKγ-PNA) in the middle of the PNA oligomer. The LKγ-PNA side chains project away from the nucleobase pairs (purple) and line the periphery of the duplex. This strategy can be used for the multifunctional display of various functional groups from the PNA residues without diminishing the binding affinity or selectivity to DNA. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1414 / 1418
页数:5
相关论文
共 46 条
[1]   Specific versus nonspecific binding of cationic PNAs to duplex DNA [J].
Abibi, A ;
Protozanova, E ;
Demidov, VV ;
Frank-Kamenetskii, MD .
BIOPHYSICAL JOURNAL, 2004, 86 (05) :3070-3078
[2]  
BIAZMOCHON JJ, 2005, CHEM COMMUN, P3316
[3]   STABILITY OF PEPTIDE NUCLEIC-ACIDS IN HUMAN SERUM AND CELLULAR-EXTRACTS [J].
DEMIDOV, VV ;
POTAMAN, VN ;
FRANKKAMENETSKII, MD ;
EGHOLM, M ;
BUCHARD, O ;
SONNICHSEN, SH ;
NIELSEN, PE .
BIOCHEMICAL PHARMACOLOGY, 1994, 48 (06) :1310-1313
[4]   Convergent synthesis of peptide nucleic acids by native chemical Ligation [J].
Dose, C ;
Seitz, O .
ORGANIC LETTERS, 2005, 7 (20) :4365-4368
[5]   Cell-permeable GPNA with appropriate backbone stereochemistry and spacing binds sequence-specifically to RNA [J].
Dragulescu-Andrasi, A ;
Zhou, P ;
He, GF ;
Ly, DH .
CHEMICAL COMMUNICATIONS, 2005, (02) :244-246
[6]   A simple γ-backbone modification preorganizes peptide nucleic acid into a helical structure [J].
Dragulescu-Andrasi, Anca ;
Rapireddy, Srinivas ;
Frezza, Brian M. ;
Gayathri, Chakicherla ;
Gil, Roberto R. ;
Ly, Danith H. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10258-10267
[7]   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
[8]   PNA HYBRIDIZES TO COMPLEMENTARY OLIGONUCLEOTIDES OBEYING THE WATSON-CRICK HYDROGEN-BONDING RULES [J].
EGHOLM, M ;
BUCHARDT, O ;
CHRISTENSEN, L ;
BEHRENS, C ;
FREIER, SM ;
DRIVER, DA ;
BERG, RH ;
KIM, SK ;
NORDEN, B ;
NIELSEN, PE .
NATURE, 1993, 365 (6446) :566-568
[9]   Synthesis of γ-substituted peptide nucleic acids: A new place to attach fluorophores without affecting DNA binding [J].
Englund, EA ;
Appella, DH .
ORGANIC LETTERS, 2005, 7 (16) :3465-3467
[10]   Spermine conjugated peptide nucleic acids (spPNA): UV and fluorescence studies of PNA-DNA hybrids with improved stability [J].
Gangamani, BP ;
Kumar, VA ;
Ganesh, KN .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 240 (03) :778-782