13C-labeled D-ribose: chemi-enzymic synthesis of various isotopomers.
Current interest in the use of heteronuclear multidimensional NMR methods to assess the structures, conformations and/or dynamics of oligonucleotides in solution has created an immediate need for nucleosides and their derivatives labeled in various ways with stable isotopes (13C, 2H, 15N and/or 17,18O). This short review focuses exclusively on chemienzymic methods to introduce one or more 13C labels into D-ribose, a precursor to ribo- and 2'-deoxyribonucleosides. It will be demonstrated that five convenient reactions, applied in specific sequences, provide access to 26 of the 32 13C-labeled isotopomers of D-ribose in acceptable yields. While not explicitly discussed herein, these same reactions, appropriately modified, can also be used to insert one or more 2H and/or 17,18O isotopes into this aldopentose.
Serianni
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AS
Department of Chemistry and Biochemistry, University of Notre Dame, Indiana 46556.
Bondo
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PB
D002247:Carbon Isotopes; D018360:Crystallography, X-Ray; D007527:Isoenzymes; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D009838:Oligodeoxyribonucleotides / Q000737:chemistry*; D012266:Ribose / Q000737:chemistry*
D002247:Carbon Isotopes; D007527:Isoenzymes; D009838:Oligodeoxyribonucleotides; D012266:Ribose