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Nucleic Acids Research, 1992, Vol. 20, No. 21 5607-5615
© 1992


CHEMISTRY

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

Dasari M. Reddy, Pamela F. Crain, Charles G. Edmonds+, Ramesh Gupta1, Takeshi Hashizume, Karl O. Stetter2, Friedrich Widde3,§ and James A. McCloskey*

Departments of Medicinal Chemistry and Biochemistry, University of Utah Salt Lake City, UT 84112 1Southern Illinois University School of Medicine Carbondale, IL 62901 2Lehrstuhl für Mikrobiologie, Universität Regensburg Germany 3Department of Microbiology, University of Illinois Urbana, IL 61801, USA

* To whom correspondence should be addressed

Received August 25, 1992. Revised October 5, 1992. Accepted October 5, 1992.

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-ß-D-ribofuranosyl-9H- purin-6-yl)amino]carbonyl]norvaline, (hn6A), structure 1, and 3-hydroxy-N-[[(9-ß-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.


+Present addresses: Battelle Pacific Northwest Laboratories, Richland, WA 99352, USA

§Max-Planck-Institut für Marine Mikrobiologie, BITZ, Fahrenheitstrasse 1, W-2800 Bremen 33, Germany


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