103597-19-9Relevant articles and documents
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
supporting information, 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.
Simple synthesis of D-erythro- and L-erythro-D-gluco-octoses
Jarosz,Skora,Kosciolowska
, p. 1797 - 1802 (2007/10/03)
Synthesis of the previously unknown methyl 2,3,4-tri-O-benzyl-L-erythro-β-D-gluco-and D-erythro-α-D-gluco-oct-1,5-pyranosides (1 and 2) was accomplished on two independent routes via either cis-hydroxylation of stereoisomeric 6-C-vinyl-L-glycero-β-D-gluco
Chain-extension of carbohydrates. 5. Synthesis of the C-glycosyl amino acid moiety of miharamycins involving stereocontrolled ethynylation of methyl 2,3,4-tri-O-benzyl-α-D-gluco-hexodialdo-1,5-pyranoside
Czernecki,Horns,Valery
, p. 650 - 655 (2007/10/02)
A multistep synthesis of the C-glycosyl amino acid moiety of miharamycins from methyl 2,3,4-tri-O-benzyl-α-D-gluco-hexodialdo-1,5-pyranoside (1) is described. The ethynyl group was employed as a synthetic equivalent of the carboxylic acid function. In the