83051-88-1Relevant articles and documents
A five-component one-pot synthesis of phosphatidylinositol pentamannoside (PIM5)
Wang, Dong,Xiong, De-Cai,Ye, Xin-Shan
, p. 1340 - 1342 (2018/01/08)
A practical and efficient synthesis of phosphatidylinositol pentamannoside (PIM5) was achieved based on a five-component one-pot sequential glycosylation protocol with exclusive regio- and stereo-selectivity. Two regioselective sequential glycosylations on inositol and p-tolyl thioglycosides as the sole type of building blocks made this protocol to avoid the tedious protective group manipulations. This synthetic strategy provides access to other important glycolipids with similar structures.
Construction of the octose 8-phosphate intermediate in lincomycin A biosynthesis: Characterization of the reactions catalyzed by LmbR and LmbN
Sasaki, Eita,Lin, Chia-I,Lin, Ke-Yi,Liu, Hung-Wen
, p. 17432 - 17435 (2013/01/15)
Lincomycin A is a potent antimicrobial agent noted for its unusual C1 methylmercapto-substituted 8-carbon sugar. Despite its long clinical history for the treatment of Gram-positive infections, the biosynthesis of the C 8-sugar, methylthiolincosamide (MTL), is poorly understood. Here, we report our studies of the two initial enzymatic steps in the MTL biosynthetic pathway leading to the identification of d-erythro-d-gluco-octose 8-phosphate as a key intermediate. Our experiments demonstrate that this intermediate is formed via a transaldol reaction catalyzed by LmbR using d-fructose 6-phosphate or d-sedoheptulose 7-phosphate as the C3 donor and d-ribose 5-phosphate as the C5 acceptor. Subsequent 1,2-isomerization catalyzed by LmbN converts the resulting 2-keto C8-sugar (octulose 8-phosphate) to octose 8-phosphate. These results provide, for the first time, in vitro evidence for the biosynthetic origin of the C8 backbone of MTL.
Ring-closing metathesis as a new strategy for the C-C coupling of monosaccharide derivatives via silicon tethering
Lobbel, Michael,Koell, Peter
, p. 393 - 396 (2007/10/03)
Suitable carbohydrate-derived terminal olefins have been coupled by ring-closing metathesis reaction following a silicon tethering strategy, generating very long contiguous chains of carbon atoms each equipped with specific stereochemistry and functionali