Ionic liquid mediated synthesis of labelled peptide nucleic acid monomer

被引:1
作者
Athira, C. K. [1 ]
Manikandan, Priyadharshini [1 ]
Kandasamy, Elango [1 ]
Ramani, Prasanna [1 ]
机构
[1] Amrita Vishwa Vidyapeetham, Amrita Sch Engn, Dept Sci, Dhanvanthri Lab, Coimbatore, Tamil Nadu, India
关键词
amino acids; peptide nucleic acids; alkylation; ionic liquids; phthalimides; PNA; RNA;
D O I
10.1016/j.matpr.2019.05.271
中图分类号
T [工业技术];
学科分类号
08 ;
摘要
We have designed and synthesized phthalimido labelled peptide nucleic acid (PNA) monomer through N-alkylation of a-amino acid ester with N-bromo ethylphthalimide which was facilitated by using ionic liquids. The alkylated product was condensed with nucleobase such as thymine-1-acetic acid to get the target compound. The labelled-PNA monomer is a new molecule which bears a marker and can be easily prepared in two steps. (C) 2019 Published by Elsevier Ltd.
引用
收藏
页码:1735 / 1739
页数:5
相关论文
共 18 条
[1]   Synthesis of of peptide nucleic acids (PNA) with a crosslinking agent to RNA and effective inhibition of dicer [J].
Akisawa, Takuya ;
Yamada, Ken ;
Nagatsugi, Fumi .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (24) :5902-5906
[2]   Imaging of RNA in live cells [J].
Armitage, Bruce A. .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2011, 15 (06) :806-812
[3]   Electrochemical activity of new ferrocene-labelled PNA monomers to be applied for DNA detection: Effects of the molecular structure and of the solvent [J].
Baldoli, C ;
Licandro, E ;
Maiorana, S ;
Resemini, D ;
Rigamonti, C ;
Falciola, L ;
Longhi, M ;
Mussini, PR .
JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 2005, 585 (02) :197-205
[4]   Synthesis and characterization of a peptide nucleic acid conjugated to a D-peptide analog of insulin-like growth factor 1 for increased cellular uptake [J].
Basu, S ;
Wickstrom, E .
BIOCONJUGATE CHEMISTRY, 1997, 8 (04) :481-488
[5]   Metal-Free, Ionic Liquid-Mediated Synthesis of Functionalized Quinolines [J].
Bharate, Jaideep B. ;
Bharate, Sandip B. ;
Vishwakarma, Ram A. .
ACS COMBINATORIAL SCIENCE, 2014, 16 (11) :624-630
[6]   Peptide nucleic acids: versatile tools for gene therapy strategies [J].
Dean, DA .
ADVANCED DRUG DELIVERY REVIEWS, 2000, 44 (2-3) :81-95
[7]   PNA-based artificial nucleases as antisense and anti-miRNA oligonucleotide agents [J].
Gaglione, M. ;
Milano, G. ;
Chambery, A. ;
Moggio, L. ;
Romanelli, A. ;
Messere, A. .
MOLECULAR BIOSYSTEMS, 2011, 7 (08) :2490-2499
[8]  
Gupta Anjali, 2017, J. appl. res. technol, V15, P122, DOI 10.1016/j.jart.2017.01.006
[9]   Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis. 2 [J].
Hallett, Jason P. ;
Welton, Tom .
CHEMICAL REVIEWS, 2011, 111 (05) :3508-3576
[10]   Synthesis and properties of peptide nucleic acid labeled at the N-terminus with HiLyte Fluor 488 fluorescent dye [J].
Hnedzko, Dziyana ;
McGee, Dennis W. ;
Rozners, Eriks .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (18) :4199-4205