TY - JOUR
T1 - Synthesis and duplex DNA recognition studies of oligonucleotides containing a ureido isoindolin-1-one homo-N-nucleoside. A comparison of host-guest and DNA recognition studies
AU - Mertz, Eric
AU - Mattei, Sebastiano
AU - Zimmerman, Steven C.
N1 - Funding Information:
We wish to thank the W. M. Keck Center for Comparative and Functional Genomics for assistance with oligonucleotide synthesis. Funding for this work was generously provided by the University of Illinois and the National Institutes of Health.
PY - 2004/3/15
Y1 - 2004/3/15
N2 - In an effort to construct non-natural bases to be used in triplex-based antigene DNA recognition strategies, a uriedo-isoindolin-1-one homo-N-nucleoside base was designed to bind the cytosine-guanine (CG) base pair. An organic soluble analogue of this base was shown to effectively complex CG (Kassoc=740 M-1) in chloroform through formation of three hydrogen bonds (Mertz, E.; Mattei, S.; Zimmerman, S. C. Org. Lett. 2000, 2, 2931-2934). The novel nucleoside base was synthesized and successfully incorporated into oligonucleotides which were used in triple helix melting temperature studies. Low melting temperatures were observed when the isoindolin-1-one base was paired opposite CG as well as GC, TA, and AT, thus indicating that despite favorable recognition in model studies, the artificial base did not effectively recognize duplex DNA to form pyrimidine-purine- pyrimidine type triple helices.
AB - In an effort to construct non-natural bases to be used in triplex-based antigene DNA recognition strategies, a uriedo-isoindolin-1-one homo-N-nucleoside base was designed to bind the cytosine-guanine (CG) base pair. An organic soluble analogue of this base was shown to effectively complex CG (Kassoc=740 M-1) in chloroform through formation of three hydrogen bonds (Mertz, E.; Mattei, S.; Zimmerman, S. C. Org. Lett. 2000, 2, 2931-2934). The novel nucleoside base was synthesized and successfully incorporated into oligonucleotides which were used in triple helix melting temperature studies. Low melting temperatures were observed when the isoindolin-1-one base was paired opposite CG as well as GC, TA, and AT, thus indicating that despite favorable recognition in model studies, the artificial base did not effectively recognize duplex DNA to form pyrimidine-purine- pyrimidine type triple helices.
KW - DNA Recognition
KW - Nucleoside
KW - Triplex DNA
UR - http://www.scopus.com/inward/record.url?scp=1542331584&partnerID=8YFLogxK
U2 - 10.1016/j.bmc.2003.12.022
DO - 10.1016/j.bmc.2003.12.022
M3 - Article
C2 - 15018925
AN - SCOPUS:1542331584
SN - 0968-0896
VL - 12
SP - 1517
EP - 1526
JO - Bioorganic and Medicinal Chemistry
JF - Bioorganic and Medicinal Chemistry
IS - 6
ER -