Structure determination of two new amino acid-containing derivatives of adenosine from tRNA of thermophilic bacteria and archaea

• Published in: Nucleic acids research Vol. 20; no. 21; pp. 5607 - 5615
• Main Authors: Reddy, Dasari M., Crain, Pamela F., Edmonds, Charles G., Gupta, Ramesh, Hashizume, Takeshi, Stetter, Karl O., Widde, Friedrich, McCloskey, James A.
• Format: Journal Article
• Language: English
• Published: Oxford Oxford University Press 11-11-1992
• Subjects: Adenosine - chemistry; Analytical, structural and metabolic biochemistry; Archaea; Archaea - genetics; Bacteria - genetics; Biological and medical sciences; Chromatography, High Pressure Liquid; Fundamental and applied biological sciences. Psychology; Gram-Negative Anaerobic Bacteria - genetics; Mass Spectrometry; Methanococcus; Methanolobus; Molecular Structure; Molecular Weight; Nucleic Acid Conformation; Nucleic acids; Nucleosides - chemistry; Pyrobaculum islandicum; Pyrococcus furiosus; RNA, Bacterial - chemistry; Rna, ribonucleoproteins; RNA, Transfer - chemistry; Thermococcus; Thermodesulfobacterium; Thermotoga maritima; Gas chromatography; t-RNA; Molecular structure; Archaeobacteria; Bacteria; Adenine nucleotide; Mass spectrometry
• ISSN: 0305-1048; 1362-4962
• DOI: 10.1093/nar/20.21.5607

Two new nucleosides have been identified in unfractionated transfer RNA of two thermophilic bacteria, Thermodesulfobacterium commune, and Thermotoga maritima, six hyperthermophlic archaea, including Pyrobaculum islandicum, Pyrococcus furiosus and Thermococcus sp. and two mesophilic archaea, Methanococcus vannielii and Methanolobus tindarius Structures were determined primarily by mass spectro-metry, as 3-hydroxy-/N-[[(9-β-D-ribofuranosyl-9H- purin-6-yl)amino]carbonyl]norvaline, (hn6A), structure 1, and 3-hydroxy-N-[[(9-β-D-ribofuranosyl-9H-2-methyl-thiopurin-6-yl)amino]carbonyl]norvaline (ms2hn6A), 2. The amino acid side chain was characterized as 3-hydroxynorvaline (3) by gas chromatography-mass spectrometry of the trimethylsilyl derivative after cleavage from 1 and 2 by alkaline hydrolysis. Evidence for the amino acid-purine carbamoyl linkage was obtained from the collision-induced dissociation mass spectrum of trimethylsilylated 1, and the total structure was confirmed bv chemical svnthesis of 1.