Synthesis of the analogue nucleoside 3-deaza-2′-deoxycytidine and its template activity with DNA polymerase

Searls, Tim; McLaughlin, Larry W.

doi:10.1016/s0040-4020(99)00703-6

Cited by 18 publications

(12 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interactions that interfere with complementary hydrogen‐bonding usually lead to dramatic duplex destabilization 26, 27. In addition to hydrogen‐bonding interactions, inter‐residue base‐stacking effects are critical to effective duplex formation.…”

Section: Discussionmentioning

confidence: 99%

Effects of the minor groove pyrimidine nucleobase functional groups on the stability of duplex DNA: The impact of uncompensated minor groove amino groups

Sun

McLaughlin

2007

Biopolymers

Self Cite

View full text Add to dashboard Cite

DNA sequences containing four types of analog nucleosides are described. All four are pyridine derivatives constructed as C-nucleosides so that they mimic the pyrimidine derivatives 2'-deoxyuridine, thymidine or 2'-deoxycytidine, but in all cases the analogs lack the corresponding O2-carbonyls that in duplex DNA are located in the minor groove. In place of the O2-carbonyl is a hydrogen atom, a polar fluorine atom, or a nonpolar methyl group. The described C-nucleosides have native-like bidentate Watson-Crick hydrogen-bonding faces and can form essentially normal W-C base pairs of varying stability with A or G. In each modified base pair, two inter-residue hydrogen bonds should be present. In spite of a common number of interstrand hydrogen bonds, the thermodynamic stabilities of the prepared duplexes, each containing two analog base pairs, vary dramatically. Most notably, base pairs containing uncompensated purine amino groups (those lacking a hydrogen-bonding partner) in the minor groove exhibit the most dramatic reductions in thermodynamic stability. Removal of such uncompensated amino groups results in increased duplex stability. Base pairs containing fluorine in the minor groove positioned adjacent to an amino group seem to enhance duplex stability marginally (relative to --H or --CH(3)), but there is little evidence to suggest that fluorine is an effective hydrogen-bonding partner in these systems. The presence of minor groove methyl groups results in the least stable duplexes in each series of sequences.

show abstract

Section: Discussionmentioning

confidence: 99%

Effects of the minor groove pyrimidine nucleobase functional groups on the stability of duplex DNA: The impact of uncompensated minor groove amino groups

Sun

McLaughlin

2007

Biopolymers

Self Cite

View full text Add to dashboard Cite

show abstract

“…The 3-deaza-C phosphoramidite was prepared as described previously. 23 Oligonucleotides containing 3-deaza-C and 4-thio-U were synthesized using 5 0 -O-dimethoxytrityl protected phosphoramidites on a Mermade 4 DNA synthesizer. Oligonucleotides were purified by reversed phase HPLC (Agilent 1100) on a Luna 5 lm C18 (2) 100 Å 250 mm Â 4.60 mm column (Phenomenex), and were eluted with acetonitrile and 50 mM triethylammonium acetate buffer using a gradient of 5-50% acetonitrile over 24 min.…”

Section: Oligonucleotidesmentioning

confidence: 99%

Oligonucleotide probes containing pyrimidine analogs reveal diminished hydrogen bonding capacity of the DNA adduct O6-methyl-G in DNA duplexes

Angelov¹,

Dahlmann²,

Sturla³

2013

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

“…This procedure has also been used to prepare 3-deaza-2 0 -deoxycytidine phosphoramidite. 48 Triazine derivatives and their nucleosides, 52,53 such as 6-azauridine, show a wide spectrum of antiviral activity against DNA and RNA viruses. 54 Several compounds with this structure have been synthesized and evaluated against parainfluenza type-1 SV.…”

Section: A Pyrimidine and Purine Derivativesmentioning

confidence: 99%

“…54 Several compounds with this structure have been synthesized and evaluated against parainfluenza type-1 SV. Salicylhydrazones of asymmetrical triazines (47)(48)(49) (Fig. 10) and the corresponding copper complexes show anti-SVactivity associated to a superoxide radical scavenger activity.…”

Section: A Pyrimidine and Purine Derivativesmentioning

confidence: 99%

Recent advances in the chemistry of parainfluenza‐1 (Sendai) virus inhibitors

Saladino

Ciambecchini

Nencioni

et al. 2003

Medicinal Research Reviews

View full text Add to dashboard Cite

show abstract

Synthesis of the analogue nucleoside 3-deaza-2′-deoxycytidine and its template activity with DNA polymerase

Cited by 18 publications

References 18 publications

Effects of the minor groove pyrimidine nucleobase functional groups on the stability of duplex DNA: The impact of uncompensated minor groove amino groups

Effects of the minor groove pyrimidine nucleobase functional groups on the stability of duplex DNA: The impact of uncompensated minor groove amino groups

Oligonucleotide probes containing pyrimidine analogs reveal diminished hydrogen bonding capacity of the DNA adduct O6-methyl-G in DNA duplexes

Recent advances in the chemistry of parainfluenza‐1 (Sendai) virus inhibitors

Contact Info

Product

Resources

About