Synthesis and binding affinity of a chiral PNA analogue

被引:16
作者
Li, Y [1 ]
Jin, T [1 ]
Liu, KL [1 ]
机构
[1] Beijing Inst Pharmacol & Toxicol, Beijing 100850, Peoples R China
关键词
D O I
10.1081/NCN-100105906
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of a chiral peptide nucleic acid (PNA), which is composed of N-aminoethyl-cis-4-nucleobase-L-proline units, was described. The chiral PNA monomers containing all four nucleobases (A., T, C and G) were steroselectively prepared. The x-ray diffraction data from a single crystal confirmed the configuration of a key intermediate. Binding activity of the oligomers with their complementary DNA targets was also investigated.
引用
收藏
页码:1705 / 1721
页数:17
相关论文
共 20 条
[1]   A CONVENIENT SYNTHESIS OF TERT-BUTYL N-(2-BROMOETHYL)CARBAMATE [J].
BEYLIN, VG ;
GOEL, OP .
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1987, 19 (01) :78-80
[2]   NOVEL ISOMERIC DIDEOXYNUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS [J].
BOLON, PJ ;
SELLS, TB ;
NUESCA, ZM ;
PURDY, DF ;
NAIR, V .
TETRAHEDRON, 1994, 50 (26) :7747-7764
[3]   Cis (1S,3R)-1-(9-adenyl)-3-hydroxycyclopentane inhibits the respiratory burst from polymorphonuclear leukocytes and has in vivo efficacy in an acute and chronic model of inflammation [J].
Borcherding, DR ;
Butler, BT ;
Linnik, MD ;
Mehdi, S ;
Dudley, MW ;
Edwards, CK .
NUCLEOSIDES & NUCLEOTIDES, 1996, 15 (05) :967-979
[4]   Affinity capture and recovery of DNA at femtomolar concentrations with peptide nucleic acid probes [J].
Chandler, DP ;
Stults, JR ;
Anderson, KK ;
Cebula, S ;
Schuck, BL ;
Brockman, FJ .
ANALYTICAL BIOCHEMISTRY, 2000, 283 (02) :241-249
[5]   Aminoethylprolyl peptide nucleic acids (aepPNA):: Chiral PNA analogues that form highly stable DNA:aepPNA2 triplexes [J].
D'Costa, M ;
Kumar, VA ;
Ganesh, KN .
ORGANIC LETTERS, 1999, 1 (10) :1513-1516
[6]   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
[7]   SYNTHESIS OF PEPTIDE NUCLEIC-ACID MONOMERS CONTAINING THE 4 NATURAL NUCLEOBASES - THYMINE, CYTOSINE, ADENINE, AND GUANINE AND THEIR OLIGOMERIZATION [J].
DUEHOLM, KL ;
EGHOLM, M ;
BEHRENS, C ;
CHRISTENSEN, L ;
HANSEN, HF ;
VULPIUS, T ;
PETERSEN, KH ;
BERG, RH ;
NIELSEN, PE ;
BUCHARDT, O .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (19) :5767-5773
[8]   alpha-PNA: A novel peptide nucleic acid analogue of DNA [J].
Howarth, NM ;
Wakelin, LPG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5441-5450
[9]   REGIOSELECTIVE ALKYLATION OF 6-(BETA-METHOXYETHOXY)GUANINE TO GIVE 9-ALKYLGUANINE DERIVATIVE [J].
KJELLBERG, J ;
LILJENBERG, M ;
JOHANSSON, NG .
TETRAHEDRON LETTERS, 1986, 27 (07) :877-880
[10]   Antisense properties of peptide nucleic acid [J].
Larsen, HJ ;
Bentin, T ;
Nielsen, PE .
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION, 1999, 1489 (01) :159-166