A new synthesis of sucrose 6'-phosphate.
Sucrose 6'-phosphate (3) is the key intermediate for sucrose (1) synthesis in plants [1]. It has recently become commercially available at ca. $1500/g (Sigma). The only chemical synthesis is that of Buchanan et al. [2]. This six-step procedure, while unambiguous, gives an overall yield of only ca. 6%. We describe here a simplified route (2 steps) with an unoptimized yield of ca. 15%. Our strategy was to use a phosphorylation reagent selective for primary hydroxyl groups and thus to avoid the necessity for blocking all of the secondary ones. Sowa and Ouchi [3] described a suitable system which they used very effectively for the synthesis of 5'-nucleotides from unprotected nucleosides. We applied this reagent to 2,1':4,6-di-O-isopropylidenesucrose (2) [4] in which the only unprotected primary hydroxyl group is that at the 6'-position (Scheme 1). The identity of the product was established by comparison of its rotation with the literature value and by the correspondence of its 1H and 13C NMR spectra with those of an authentic sample synthesized by Buchanan's method (Sigma) 1H assignments were made with the help of the assignments of du Penhoat et al. [5] for sucrose and the results of a one-bond H-C COSY experiment (Fig. 1). The 13C spectrum showed that all of the resonances were shifted downfield by ca. 0.5 ppm as compared with sucrose [6] except for the C-5' doublet which was shifted upfield by 0.5 ppm and the C-6' doublet which was shifted downfield by 2.2 ppm (Table 1).
Kim
K B
KB
Department of Biochemistry, Ohio State University, Columbus, 43210, USA.
Behrman
E J
EJ
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry
D013403:Sugar Phosphates; C535046:sucrose-6-phosphate; D013395:Sucrose