13C and15N NMR chemical shift assignments ofN-1-(2- azidoethyl)-4-R-pyrimidin-2-ones by1H,X HMQ(B)C withz-gradient selection

Kolehmainen, Erkki; Lappalainen, Kari; Šaman, David; Holý, Antonı́n; Gunter, J. D.

doi:10.1002/(sici)1097-458x(199806)36:6<442::aid-omr314>3.0.co;2-g

Cited by 5 publications

(7 citation statements)

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“…Supporting evidence came from experimental and DFT calculated isotopic IR shifts (Table ). The 15 N NMR experimental chemical shifts closely matched DFT chemical shift calculations (Table ) and were consistent with observed chemical shifts in previous literature studies …”

Section: Resultssupporting

confidence: 90%

“…The 15 N NMR experimental 2) and were consistent with observed chemical shifts in previous literature studies. 51 The 15 N chemical shift demonstrated different sensitivity to the change of the local solvent environment depending upon the position of the 15 N atom within the azido probe. The 4).…”

Section: Resultsmentioning

confidence: 99%

“…In this context, indirect detect 2D NMR methods such as HMBC may be preferred. This technique was successfully used to obtain natural abundance 15 N NMR spectra of both internal and middle nuclei of an azido group, 51 which suggests these methods will be applicable to 1i or 1m incorporated into oligonucleotides. Similar to the IR results, the 15 N chemical shift of the azide probe in 3m was found to remain essentially unchanged (∆δ 15 N ) 0.05 ppm) upon heterodimer formation with 4 in deuterochloroform.…”

Section: Resultsmentioning

confidence: 99%

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A Sensitive Multispectroscopic Probe for Nucleic Acids

2010

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Azides have recently been used as vibrational probes of proteins, but their incorporation into nucleic acids has been limited to photo-cross-linking or click chemistry applications. The utility of 2'-azido-2'-deoxyuridine (N(3)-dU, 1) as an IR and (15)N NMR spectroscopic probe of the sugar phosphate backbone region of nucleic acids was investigated by measuring the effects of solvent, heterodimer formation, and temperature on peak frequencies and IR bandwidth. The azide IR asymmetric stretching band (nu(N(3))) of N(3)-dU was sensitive to its environment, undergoing a blue shift of 13.5 cm(-1) when changing the solvent from THF to water. The solvent effects on (15)N chemical shifts (delta((15)N)) of each of the nitrogen atoms in the azido group was studied, and the terminal nitrogen atom was the most sensitive to solvent, shifting downfield by 3.8 ppm when changing the solvent from THF-d(8) to D(2)O. Formation of a base-pair-like heterodimer between 3 (a silyl ether analogue of 1) and 2,6-diheptanamidopyridine (4) in chloroform resulted in minimal changes in the IR and (15)N NMR spectral frequency and chemical shift, respectively, as expected given the location of the azido moiety. The intrinsic temperature dependence of nu(N(3)) and delta((15)N) were found to be minimal over the temperature range studied especially compared to the solvent dependence of these spectral observables. The analysis of the experimental studies was complemented by density functional theory (DFT) calculations on model systems.

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Section: Resultssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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A Sensitive Multispectroscopic Probe for Nucleic Acids

2010

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“…2-Azidoethylpyrimidin-2-ones. A study of the 15 N chemical shifts and long-range couplings of a series of 4-substituted 1-(2-azidoethyl)pyrimidin-2-ones ( 44 ) was recently reported by Kolehmainen and co-workers …”

Section: Applications Of Long-range 1h−15n Heteronuclear Chemical Shi...mentioning

confidence: 91%

“…A study of the 15 N chemical shifts and long-range couplings of a series of 4-substituted 1-(2-azidoethyl)pyrimidin-2-ones (44) was recently reported by Kolehmainen and co-workers. 109 Samples were prepared as saturated solutions in DMSOd 6 . The long-range delays were variously optimized for 5 or 2.5 Hz; chemical shifts were reported upfield of nitromethane and are reported here downfield of liquid ammonia.…”

Section: -Azidoethylpyrimidin-2-onesmentioning

confidence: 99%

Long-Range ¹H−¹⁵N Heteronuclear Shift Correlation at Natural Abundance

Martin¹,

Hadden²

2000

J. Nat. Prod.

193

187

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Despite the inherently low sensitivity of (15)N NMR because of its low gyromagnetic ratio (gamma(N)) and its relatively low natural abundance (0.37%), this important nuclide still has useful potential as a structural probe even at natural abundance. Inverse-detected NMR methods coupled with major advances in NMR probe designs have made it possible to acquire long-range (1)H-(15)N heteronuclear shift correlation data on samples as small as a micromole overnight. Chemical shift referencing schemes for (15)N and the range of (15)N shifts are discussed, followed by a discussion of the currently available pulse sequences, pulse calibration, parametrization and processing of long-range (1)H-(15)N data, and the implications of probe selection. These topics are followed by a review of the applications contained in the literature that have utilized (1)H-(15)N heteronuclear shift correlation experiments at natural abundance, with emphasis placed on the observed long-range coupling pathways.

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¹⁵N NMR spectroscopy of 3‐substituted 5‐trichloromethyl‐1,2‐dimethyl‐1H‐pyrazolium chlorides

Martins

Pereira

Sinhorin

et al. 2002

Magnetic Reson in Chemistry

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13C and15N NMR chemical shift assignments ofN-1-(2- azidoethyl)-4-R-pyrimidin-2-ones by1H,X HMQ(B)C withz-gradient selection

Cited by 5 publications

References 0 publications

A Sensitive Multispectroscopic Probe for Nucleic Acids

A Sensitive Multispectroscopic Probe for Nucleic Acids

Long-Range ¹H−¹⁵N Heteronuclear Shift Correlation at Natural Abundance

¹⁵N NMR spectroscopy of 3‐substituted 5‐trichloromethyl‐1,2‐dimethyl‐1H‐pyrazolium chlorides

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13C and15N NMR chemical shift assignments ofN-1-(2- azidoethyl)-4-R-pyrimidin-2-ones by1H,X HMQ(B)C withz-gradient selection

Cited by 5 publications

References 0 publications

A Sensitive Multispectroscopic Probe for Nucleic Acids

A Sensitive Multispectroscopic Probe for Nucleic Acids

Long-Range 1H−15N Heteronuclear Shift Correlation at Natural Abundance

15N NMR spectroscopy of 3‐substituted 5‐trichloromethyl‐1,2‐dimethyl‐1H‐pyrazolium chlorides

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Product

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Long-Range ¹H−¹⁵N Heteronuclear Shift Correlation at Natural Abundance

¹⁵N NMR spectroscopy of 3‐substituted 5‐trichloromethyl‐1,2‐dimethyl‐1H‐pyrazolium chlorides