Genome guided identification of 2-methylthio-N6-(4-hydroxy-isopentenyl)-adenosine from Streptomyces xinghaiensis NRRL B24674T

Abstract:

[Objective] To investigate the production of adenosine modified with N⁶-(Δ²-isopentenyl) and 2-thiomethyl groups from marine-derived Streptomyces xinghaiensis NRRL B24674^T. [Methods] Bioinformatics analysis was carried out to search the genome sequence of S. xinghaiensis NRRL B24674^T and the secondary metabolites were purified by silica gel column chromatography, gel chromatography and high-performance liquid chromatography, and the chemical structure was elucidated by nuclear magnetic resonance (NMR) and mass spectroscopy (MS). [Results] Two proteins involved in such a biosynthetic pathway were found in the genome of S. xinghaiensis NRRL B24674^T; 2-methylthio-N⁶-(4-hydroxyisopentenyl)-adenosine has been purified from the liquid culture of S. xinghaiensis NRRL B24674^T, and its chemical structure was elucidated by analysis of high-resolution mass spectrometry (HR-MS) and NMR data. [Conclusion] Such an adenine modification process was present in S. xinghaiensis NRRL B24674^T, and it is the first time to report this kind of adenine modification from actinomycetes Streptomyces. Bioinformatics analysis implies that Streptomyces can also have this kind of RNA or adenine modification.