Design, synthesis, biophysical and primer extension studies of novel acyclic butyl nucleic acid (BuNA)

被引：22

作者：

Kumar, Vipin ^{[1
]}

Gore, Kiran R. ^{[2
]}

Pradeepkumar, P. I. ^{[2
]}

Kesavan, Venkitasamy ^{[1
]}

机构：

[1] Indian Inst Technol Madras IITM, Dept Biotechnol, Biol Chem Lab, Madras 600036, Tamil Nadu, India

[2] Indian Inst Technol, Dept Chem, Bombay 400076, Maharashtra, India

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 35期

关键词：

THROMBIN BINDING APTAMER; BASE-PAIRING PROPERTIES; I-MOTIF STRUCTURE; HYBRIDIZATION PROPERTIES; NUCLEOSIDE ANALOGS; ANTISENSE OLIGONUCLEOTIDES; CHEMICAL-MODIFICATIONS; ENZYMATIC STABILITY; POLYMERASE CRYSTAL; DUPLEX FORMATION;

D O I：

10.1039/c3ob41244j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel nucleic acid analogue called acyclic (S)-butyl nucleic acid (BuNA) composed of an acyclic backbone containing a phosphodiester linkage and bearing natural nucleobases was synthesized. Next, (S)-BuNA nucleotides were incorporated in DNA strands and their effect on duplex stability and changes in structural conformation were investigated. Circular dichroism (CD), UV-melting and non-denatured gel electrophoresis (native PAGE) studies revealed that (S)-BuNA is capable of making duplexes with its complementary strands and integration of (S)-BuNA nucleotides into DNA duplex does not alter the B-type-helical structure of the duplex. Furthermore, (S)-BuNA oligonucleotides and (S)-BuNA substituted DNA strands were studied as primer extensions by DNA polymerases. This study revealed that the acyclic scaffold is tolerated by enzymes and is therefore to some extent biocompatible.

引用

页码：5853 / 5865

页数：13

共 50 条

[21] STUDIES ON NUCLEIC ACID AND NUCLEIC ACID ANALOGS .2. SYNTHESIS OF 1-METHYLHYPOXANTHINE
YAMAOKA, N
ASO, K
NIPPON NOGEI KAGAKU KAISHI, 1961, 35 (03): : 280 - &
[22] STUDIES OF NUCLEIC ACID SYNTHESIS IN ASCITES TUMOR CELLS
LEPAGE, GA
GREENLEES, J
FERNANDES, JF
ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1956, 63 (05) : 999 - 1007
[23] Peptide nucleic acid synthesis by novel amide formation
Lee, Hyunil
Jeon, Jae Hoon
Lim, Jong Chan
Choi, Hoon
Yoon, Yeohong
Kim, Sung Kee
ORGANIC LETTERS, 2007, 9 (17) : 3291 - 3293
[24] Design, synthesis, and evaluation of novel biarylpyrimidines: A new class of ligand for unusual nucleic acid structures
Wheelhouse, Richard T.
Jennings, Sharon A.
Phillips, Victoria A.
Pletsas, Dimitrios
Murphy, Peter M.
Garbett, Nichola C.
Chaires, Jonathan B.
Jenkins, Terence C.
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (17) : 5187 - 5198
[25] ACYCLIC NUCLEIC-ACID ANALOGS - SOLID-PHASE SYNTHESIS OF MODIFIED POLYURETHANES AND POLYPEPTIDES
NELSON, JS
WELLER, DD
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1992, 203 : 98 - ORGN
[26] INHIBITION OF NUCLEIC-ACID SYNTHESIS BY DI-N-BUTYL ESTER OF METHOTREXATE
CURT, GA
TOBIAS, JS
KRAMER, RA
ROSOWSKY, A
PARKER, LM
TATTERSALL, MHN
BIOCHEMICAL PHARMACOLOGY, 1976, 25 (17) : 1943 - 1946
[27] ORGN 786-Design, synthesis and anion binding studies of a series of novel, acyclic anion binding agents
Sessler, Joanthan L.
Barkey, Natalie
Pantos, G. Dan
Gale, Philip A.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
[28] 6′-Fluoro[4.3.0]bicyclo nucleic acid: synthesis, biophysical properties and molecular dynamics simulations
Frei, Sibylle
Istrate, Andrei
Leumann, Christian J.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 3088 - 3097
[29] Design, synthesis and DNA/RNA binding studies of nucleic acids comprising stereoregular and acyclic polycarbamate backbone: polycarbamate nucleic acids (PCNA) (vol 8, pg 3734, 2010)
Madhuri, Vangala
Kumar, Vaijayanti A.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (24) : 5700 - 5700
[30] Design, Synthesis, and Biophysical Studies of Novel 1,2,3-Triazole-Based Quinoline and Coumarin Compounds
Paul, Sandip
Roy, Pritam
Sardar, Pinki Saha
Majhi, Anjoy
ACS OMEGA, 2019, 4 (04): : 7213 - 7230

← 1 2 3 4 5 →