Nucleic acids and alkylating agents: Carbon-13 magnetic resonance studies of the methylation of ribonucleic acid with methyl methanesulfonate

Chang, Ching‐Jer; Lee, Chi-Gen

doi:10.1016/0003-9861(76)90225-3

Cited by 7 publications

(1 citation statement)

References 13 publications

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“…Chang and Lee (11) were able to identify methyl carbon resonances from five methylated nucleosides (m7G, m A, m3C, m G and methyl phosphate) in a natural-abundance 13C-NMR spectrum of unfractionated yeast tRNA methylated in vitro by treatment with an alkylating agent, methyl methanesulfonate. A large improvement in the signal-to-noise ratio was observed with the use of a 13C-enriched methylating agent.…”

Section: Introductionmentioning

confidence: 99%

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Agris

Schmidt

1980

Nucl Acids Res

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Methyl carbon-13 NMR spectra of purified tRNA species are presented for the first time. In addition, these spectra of tRNA species specific for phenylalanine, tyrosine, and cysteine exhibited the first resolution of single methyl carbon resonances. Carbon-13 enriched methyl groups of ribothymidine (T) and 7-methylguanosine (m7G) and the methylthio group of 2-methylthio-N6-(delta2-isopentenyl) adenosine (ms2i6A) were resolved. The T methyl signal of tRNAPhe shifted from 12.3 ppm at 45 degrees in the absence of added Mg2+ to 11.1 ppm at 30 degrees in the presence of 10mM MgCl2. The same change in conditions led to a 0.4 ppm shift of the m7G methyl signal in the opposite direction. The relative ease in obtainment of single carbon resonances of purified tRNA species, and display of the sensitivity of their chemical shifts to changes in local structure, are requisite criteria for 13C-NMR to be a useful technique in probing tRNA conformation and its changes during interaction with proteins and other nucleic acids.

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Section: Introductionmentioning

confidence: 99%

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Agris

Schmidt

1980

Nucl Acids Res

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Synthesis of [2‐¹³C, 2‐¹⁴C]2‐aminoethanol, [1‐¹³C, 1‐¹⁴C]2‐chloroethylamine, N,N′‐bis([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(BCNU) and N‐([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(CNU)

Narayan¹,

Chang²

1982

Labelled Comp Radiopharmac

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[2‐13C, 2‐14C]2‐Aminoethanol hydrochloride was prepared in good yield from Na*CN in a two step sequence by first converting the Na*CN to OHCH2*CN and then reducing the nitrile directly with a solution of borane‐tetrahydrofuran complex. The reaction procedure was simple and the pure product could be obtained readily. Using this specifically labelled precursor, the synthesis of [1‐13C, 1‐14C]2‐chloroethylamine hydrochloride, N‐([1‐13C, 1‐14C]2‐chloroethyl)‐N‐nitrosourea(CNU) and N,N′‐bis([1‐13C, 1‐14C]2‐chloroethyl)‐N‐nitrosourea(BCNU) in good yield without isotope scrambling was also reported.

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¹³C NMR studies of methylnucleosides

et al. 1984

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Nucleic acids and alkylating agents: Carbon-13 magnetic resonance studies of the methylation of ribonucleic acid with methyl methanesulfonate

Cited by 7 publications

References 13 publications

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Synthesis of [2‐¹³C, 2‐¹⁴C]2‐aminoethanol, [1‐¹³C, 1‐¹⁴C]2‐chloroethylamine, N,N′‐bis([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(BCNU) and N‐([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(CNU)

¹³C NMR studies of methylnucleosides

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Nucleic acids and alkylating agents: Carbon-13 magnetic resonance studies of the methylation of ribonucleic acid with methyl methanesulfonate

Cited by 7 publications

References 13 publications

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from13C-enriched, purified species

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from13C-enriched, purified species

Synthesis of [2‐13C, 2‐14C]2‐aminoethanol, [1‐13C, 1‐14C]2‐chloroethylamine, N,N′‐bis([1‐13C, 1‐14C]2‐chloroethyl)‐N‐nitrosourea(BCNU) and N‐([1‐13C, 1‐14C]2‐chloroethyl)‐N‐nitrosourea(CNU)

13C NMR studies of methylnucleosides

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Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Structure of transfer RNA by carbon NMR: resolution of single carbon resonances from¹³C-enriched, purified species

Synthesis of [2‐¹³C, 2‐¹⁴C]2‐aminoethanol, [1‐¹³C, 1‐¹⁴C]2‐chloroethylamine, N,N′‐bis([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(BCNU) and N‐([1‐¹³C, 1‐¹⁴C]2‐chloroethyl)‐N‐nitrosourea(CNU)

¹³C NMR studies of methylnucleosides