PNA monomers fully compatible with standard Fmoc-based solid-phase synthesis of pseudocomplementary PNA

被引：9

作者：

Sugiyama, Toru ^{[1
]}

Hasegawa, Genki ^{[1
]}

Niikura, Chie ^{[1
]}

Kuwata, Keiko ^{[2
]}

Imamura, Yasutada ^{[3
]}

Demizu, Yosuke ^{[4
]}

Kurihara, Masaaki ^{[5
]}

Kittaka, Atsushi ^{[1
]}

机构：

[1] Teikyo Univ, Fac Pharmaceut Sci, Itabashi Ku, Tokyo 1738605, Japan

[2] Nagoya Univ, Inst Transformat Biomol WPI ITbM, Chikusa Ku, Nagoya, Aichi 4648601, Japan

[3] Kogakuin Univ, Fac Engn, 2665-1 Nakano, Hachioji, Tokyo 1920015, Japan

[4] Minist Hlth & Welf Japan, Natl Inst Hlth Sci, Div Organ Chem, Setagaya Ku, Tokyo 1588501, Japan

[5] Int Univ Hlth & Welf, Sch Pharm, 2600-1 Kitakanemaru, Ohtawara, Tochigi 3248501, Japan

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 15期

基金：

日本学术振兴会;

关键词：

Peptide nucleic acid; Strand invasion; Pseudocomplementary; Antigene; PEPTIDE NUCLEIC-ACIDS; PSEUDO-COMPLEMENTARY PNA; DOUBLE-STRANDED DNA; DUPLEX DNA; RESTRICTION; EFFICIENT; ENZYMES;

D O I：

10.1016/j.bmcl.2017.06.015

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：3337 / 3341

页数：5

共 24 条

[1] Pseudo-complementary PNA actuators as reversible switches in dynamic DNA nanotechnology
Ackermann, Damian
Famulok, Michael
[J]. NUCLEIC ACIDS RESEARCH, 2013, 41 (08) : 4729 - 4739
[2] AHSt Amant, 2012, ORG BIOMOL CHEM, V10, P876
[3] STABILITY OF PEPTIDE NUCLEIC-ACIDS IN HUMAN SERUM AND CELLULAR-EXTRACTS
DEMIDOV, VV
POTAMAN, VN
FRANKKAMENETSKII, MD
EGHOLM, M
BUCHARD, O
SONNICHSEN, SH
NIELSEN, PE
[J]. BIOCHEMICAL PHARMACOLOGY, 1994, 48 (06) : 1310 - 1313
[4] Synthesis of tert-butoxycarbonyl (Boc)-protected purines
Dey, S
Garner, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (22) : 7697 - 7699
[5] PNA HYBRIDIZES TO COMPLEMENTARY OLIGONUCLEOTIDES OBEYING THE WATSON-CRICK HYDROGEN-BONDING RULES
EGHOLM, M
BUCHARDT, O
CHRISTENSEN, L
BEHRENS, C
FREIER, SM
DRIVER, DA
BERG, RH
KIM, SK
NORDEN, B
NIELSEN, PE
[J]. NATURE, 1993, 365 (6446) : 566 - 568
[6] Solution- and solid-phase parallel synthesis of 4-alkoxy-substituted pyrimidines with high molecular diversity
Font, D
Heras, M
Villalgordo, JM
[J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (03): : 311 - 321
[7] Font D, 2002, SYNTHESIS-STUTTGART, P1833
[8] Specific and nonspecific inhibition of transcription by DNA, PNA, and phosphorothioate promoter analog duplexes
Hamilton, SE
Iyer, M
Norton, JC
Corey, DR
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (23) : 2897 - 2900
[9] PNA-directed triple-helix formation by N7-xanthine
Hudson, RHE
Goncharenko, M
Wallman, AP
Wojciechowski, F
[J]. SYNLETT, 2005, (09) : 1442 - 1446
[10] Sequence-specific protection of duplex DNA against restriction and methylation enzymes by pseudocomplementary PNAs
Izvolsky, KI
Demidov, VV
Nielsen, PE
Frank-Kamenetskii, MD
[J]. BIOCHEMISTRY, 2000, 39 (35) : 10908 - 10913

← 1 2 3 →