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Nucleic Acids Research, 2001, Vol. 29, No. 7 1470-1475
© 2001 Oxford University Press

Hybrid characteristics of oligonucleotides consisting of isonucleoside 2',5'-anhydro-3'-deoxy-3'-(thymin-1-yl)-D-mannitol with different linkage modes

Zhen Lei, Ling Zhang, Liang Ren Zhang, Jun Chen, Ji Mei Min and Li He Zhang*

National Research Laboratory of Natural and Biomimetic Drugs, Peking University, 38 Xueyuan Road, Beijing 100083, People’s Republic of China

Oligonucleotides consisting of the isonucleoside repeating unit 2',5'-anhydro-3'-deoxy-3'-(thymin-1-yl)-D-mannitol (4) were synthesized with the monomeric unit 4 incorporated into oligonucleotides as 1'->4' linkage 4a (oligomer I) or 6'->4' linkage 4b (oligomer II). The hybrid properties of the two oligonucleotides I and II with their complementary strands were investigated by thermal denaturation and CD spectra. Oligonucleotide I (4a) formed a stable duplex with d(A)14 with a slightly reduced Tm value of 36.6°C, relative to 38.2°C for the control duplex d(T)14/d(A)14, but oligomer II (4b) failed to hybridize with a DNA complementary single strand. The spectrum of the duplex oligomer I/d(A)14 showed a positive CD band at 217 nm and a negative CD band at 248 nm attributable to a B-like conformation. Molecular modeling showed that in the case of oligomer I the C6' hydroxy group of each unit could be located in the groove area when hybridized to the DNA single strand, which might contribute additional hydrogen bonding to the stability of duplex formation.

* To whom correspondence should be addressed. Tel: +86 10 620 91 570; Fax: +86 10 620 92 724; Email: zdszlh{at}mail.bjmu.edu.cn


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J. Chen, L. R. Zhang, J. M. Min, and L. H. Zhang
Studies on the synthesis of a G-rich octaoligoisonucleotide (isoT)2(isoG)4(isoT)2 by the phosphotriester approach and its formation of G-quartet structure
Nucleic Acids Res., July 1, 2002; 30(13): 3005 - 3014.
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