NDLI: Oligonucleotide analogues containing a C3′-NH-C(O)-CH$

Content Provider	Springer Nature Link
Author	Varizhuk, A. M. Kochetkova, S. V. Kolgava, N. A. Timofeev, E. N. Florent’ev, V. L.
Copyright Year	2010
Abstract	A dinucleotide containing a C3′-NH-C(O)-CH$_{2}$-C5′ amide internucleotide bond was synthesized by the interaction of 3′-deoxy-3′-amino-5′-O-(tert-butyldimethylsilyl)thymidine with 3′-O-benzyl-2′-O-tert-butyldimethylsilyl-5′-deoxy-5′-carboxymethylribosylthymine, which was obtained from 2′-O-acetyl-3′-O-benzyl-5′-deoxy-5′-ethoxycarbonylmethylribosylthymine through the methanolysis of the acetyl group followed by silylation of liberated hydroxyl and ester saponification. After standard manipulation with protecting groups, the dinucleotide was converted into 3′-O(2-cyanoethyl-N,N-diisopropylphosphoramidite), which was used for the synthesis of modified oligonucleotides on an automated synthesizer. The melting curves of the duplexes formed by modified and complementary natural oligonucleotides were registered, and the melting temperatures and thermodynamic parameters of the duplex formation were calculated. The introduction of a single modified bond into the oligonucleotide led to an insignificant decrease in the melting temperature of these duplexes as compared to unmodified ones.
Starting Page	199
Ending Page	206
Page Count	8
File Format	PDF
ISSN	10681620
Journal	Russian Journal of Bioorganic Chemistry
Volume Number	36
Issue Number	2
e-ISSN	1608330X
Language	English
Publisher	SP MAIK Nauka/Interperiodica
Publisher Date	2010-04-07
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	oligonucleotides analogues amide internucleotide bond hybridization thermal stability Biomedicine general Organic Chemistry Bioorganic Chemistry Biochemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry

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