Stabilization of double-stranded oligonucleotides using backbone-linked disulfide bridges

Gao, Hewei; Yang, Meihua; Cook, Alan F.

doi:10.1093/nar/23.2.285

Cited by 25 publications

(20 citation statements)

References 19 publications

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“…In a procedure that is reminiscent of the introduction of PEG and stilbene linkers, Gao and co-workers have bridged the 5′-and 3′-hydroxyls of helices with disulfide loops (35). 120,121 A disulfide cross-linked circular oligonucleotide has also been reported. 122 In this work, two C 5 -(thiopropyne)thymidines (36) were incorporated within a single oligonucleotide strand and upon binding a complementary stand in the major groove a crosslink results.…”

Section: Figurementioning

confidence: 96%

Nucleic Acid Selection and the Challenge of Combinatorial Chemistry

1997

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Section: Figurementioning

confidence: 96%

Nucleic Acid Selection and the Challenge of Combinatorial Chemistry

1997

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“…One of the most successful approaches to the linking of two oligonucleotide strands is the introduction of thiol groups which can form a covalent disulfide bond. [21][22][23][24][25][26][27] Such crosslinks between two complementary strands can be useful in the study of mechanisms of enzymatic processing of DNA 21,23 and in the stabilization of folded structures for structural studies. 22,[24][25][26] The juxtaposition of thiols in two complementary strands makes formation of disulfide crosslinks a simple procedure under oxidative conditions.…”

Section: Introductionmentioning

confidence: 99%

Very High Affinity DNA Recognition by Bicyclic and Cross-Linked Oligonucleotides

Chaudhuri

Kool²

1995

J. Am. Chem. Soc.

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We report the synthesis and DNA incorporation of a novel C-5 thiopropyne-substituted thymidine derivative which can be used to bring about covalent crosslinks between two noncomplementary DNA strands. This modified thymine pairs normally with adenine in duplex DNA and is shown not to be destabilizing to DNA double helices. Placement of the thiol-nucleotide near the center of opposing pyrimidine strands in pyr·pur·pyr triple helices results in crosslinking of the pyrimidine strands under aerobic conditions. Thermal melting studies at neutral pH show that such crosslinked ligands bind complementary purine strands with higher affinity than is possible with simple Watson-Crick recognition alone. In addition, we describe the construction of a triplex-forming circular oligonucleotide which contains a similar disulfide link across the center. This macrobicyclic ligand binds with extremely high affinity and sequence selectivity to a complementary purine DNA strand. The formation of crosslinks across two noncomplementary strands represents a new strategy for increasing affinity and selectivity of DNA recognition.

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“…Although it is known that oxidation at the sulfur can occur, to our knowledge the reaction products were not characterized. The reactivity of the thiol allowed the formation of both intra-and intermolecular dithio bonds and was applied to the synthesis of circular oligonucleotides [9] and double stranded DNA oligomers with loops at both sides [10].…”

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confidence: 99%

Characterization and sequence verification of thiolated deoxyoligonucleotides used for microarray construction

Rozenski

2006

J. Am. Soc. Mass Spectrom.

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During synthesis of thiolated deoxyoligonucleotides, side products can be formed. When used in the fabrication of microchips, the oligonucleotides have to be of high purity. We demonstrated the presence of impurities, which were not failure sequences from the synthesis. These products were identified and characterized using high-performance liquid chromatography (HPLC) and electrospray MS(/MS). The presence of the free thiol group was assessed by acrylamide derivatization. After reaction with acrylamide the correct compounds showed a 71 u mass shift and the major fragment ions could be assigned as 5= a-base and 3= w ions, similar as for unmodified DNA. The side products were unaffected by acrylamide, suggesting that the thiol group was modified. The oligonucleotide containing a species with a mass of 32 u higher was identified as 5= sulfinic acid containing molecule and was found as 45% of the total amount of a DNA 25 mer. Other components appeared to be dithio-linked oxidation products, present about 1 to 5% in a 10 mer and 15 mer deoxyoligonucleotide. The analyses were useful for optimizing the synthesis

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Stabilization of double-stranded oligonucleotides using backbone-linked disulfide bridges

Cited by 25 publications

References 19 publications

Nucleic Acid Selection and the Challenge of Combinatorial Chemistry

Nucleic Acid Selection and the Challenge of Combinatorial Chemistry

Very High Affinity DNA Recognition by Bicyclic and Cross-Linked Oligonucleotides

Characterization and sequence verification of thiolated deoxyoligonucleotides used for microarray construction

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