J(77Se, 1H) and J(77Se, 13C) couplings of seleno‐carbohydrates obtained by 77Se satellite 1D 13C spectroscopy and 77Se selective HR‐HMBC spectroscopy. (21st May 2018)

• Record Type: Journal Article
• Authors: Uzawa, Jun; Shimabukuro, Junpei; Suzuki, Tatsuya; Imamura, Akihiro; Ishida, Hideharu; Ando, Hiromune; Yamaguchi, Yoshiki
• Is Part Of: Magnetic resonance in chemistry. Volume 56:Number 9(2018)
• Page Start: 836
• Page End: 846
• Publication Date: 2018-05-21
• Subjects: 13C -- 1H -- 77Se -- 77Se satellite 13C signal -- conformation -- coupling constant -- HR‐HMBC -- NMR -- seleno‐carbohydrates; Nuclear magnetic resonance spectroscopy -- Periodicals; Chemistry, Organic -- Periodicals; Magnetic resonance -- Periodicals; 538.36
• DOI: 10.1002/mrc.4746
• Languages: English
• ISSNs: 0749-1581

Abstract

Abstract : Seleno‐carbohydrates are those in which the oxygen of the glycosidic bond or the hydroxyl group is artificially replaced with selenium. This substitution changes 1 H and 13 C chemical shifts and produces spin coupling constants involving 77 Se. Coupling constants, such as 2‐3 J ( 77 Se, 1 H), are likely to be useful for conformational analyses of glycans because such couplings are never observed in natural glycans. Several papers have discussed the relationship between 2‐3 J ( 77 Se, 1 H) and conformation; however, only few reports describe 1‐3 J ( 77 Se, 13 C), which could also be useful. Here, we obtain 77 Se coupling constants of seleno‐carbohydrates from 77 Se‐selective HR‐HMBC and 77 Se satellites in 1D 13 C spectra and examine their conformations using the Newman projection scheme. Abstract : We performed a nuclear magnetic resonance study of seleno‐carbohydrates. The substitution of an oxygen atom with selenium potentially provides new additional nuclear magnetic resonance parameters such as J (Se, H) and J (Se, C) coupling constants. Here, J (Se, H) and J (Se, C) coupling constants were successfully obtained by use of 77 Se‐selective HR‐HMBC and 77 Se satellite 1D 13 C spectroscopy.