Systematic synthesis of specifically 13C/2H - labeled nucleosides from [ul-13C6]-d-glucose

• Published in: Tetrahedron letters 1998-04, Vol.39 (18), p.2793-2796
• Main Authors: Ono, Akira (Mei), Shiina, Toko, Ono, Akira, Kainosho, Masatsune
• Format: Article
• Language: English
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/S0040-4039(98)00432-8

A systematic approach, which combines previously reported reactions with appropriate modifications, was established for preparing a variety of selectively deuterated nucleosides from glucose. We have developed a systematic method of synthesizing specifically deuterated nucleosides from glucose. Selectively 13C/2H - doubly labeled nucleosides, such as [1′,2′,3′,4′,5′-13C5;3′,5′-2H2]- and [1′,2′,3′,4′,5′-13C5;4′,5′-2H2]-adenosines, have been synthesized starting from [ul-13C6]-d-glucose. These labeled nucleosides are very useful for precise conformational analyses of nucleic acids in solution by heteronuclear multidimensional NMR spectroscopy. A systematic approach to synthesize specifically deuterated nucleosides from glucose has been developed. A variety of 13C/2H-doubly labeled nucleosides, such as [1′, 2′, 3′, 4′, 5′-13C5;3′,5′-2H2] - and [1′, 2′, 3′, 4′, 5′-2H2]-adenosines, have been synthesized by this approach staring from [ul-13C6]-D-glucose.