20770-87-0Relevant articles and documents
A Natural Lipotrisaccharide and Its Derivatives Selectively Lyse Streptococcus pneumoniae via Interaction with Cell Membrane
Liu, Bo,Liu, Xue,Zhang, Jing-Ren,Liu, Gang
, p. 438 - 453 (2017)
A natural lipotrisaccharide (NP000778, 1a), a new triglycosidic tri-O-substituted glycolipid isolated from the Morinda citrifolia plant, and its chemical derivatives were identified to be active against major Gram-positive pathogens, particularly Streptococcus pneumoniae. Additional evidence indicated that 1a and its synthetic derivatives exerted their bactericidal activities against S. pneumoniae by selectively targeting the bacterial membrane, leading to the rapid lysis of the pneumococci. Efficient synthesis of 1a and its derivatives was performed using an application of the intramolecular aglycon delivery (IAD) reaction to establish its structure-activity relationships (SARs). SAR analysis indicated that trisaccharide glycolipid compounds showed good selectivity and high potency against S. pneumoniae. These compounds contain a linear chain with a chain length from C3 to C9 at the 2-position (R1) and 4′-position (R3), as well as a 2-methyl butyryl group at the 3′-position (R2), without an aza substitution in the lipid chain. This is the first lipotrisaccharide identified with potent bactericidal activity via interaction with cell membrane. The results reported herein offer a valuable guideline for the design of glycolipid derivatives that selectively target pathogenic bacteria.
Application of 5-C5H5)Fe(CO)2(2-methylpropene)>+BF4- for the Protection of the Allyl Group in Carbohydrate Derivatives Containing O-Allyl and O-Benzyl Groups
Stepowska, H.,Zamojski, A.
, p. 2229 - 2236 (2007/10/02)
Complex 5-C5H5)Fe(CO)2(η2-2-methylpropene)>+BF4- forms exchange complexes with the double bond in O-allyl group protected, O-benzylated sugar derivatives (6-14).From these compounds benzyl groups can be removed by catalytic hydrogenation.Decomplexation furnishes debenzylated, O-allyl groups containing products (15-22) in low to modest yields.Selective debenzylation, carbohydrates, η5-cyclopentadienyl-di(carbonyl)-η2-2-methylpropene-iron tetrafluoroborate
Synthesis, Photochemistry and Enzymology of 2-O-(2-Nitrobenzyl)-D-glucose, a Photolabile Derivative of D-Glucose
Corrie, John E. T.
, p. 2161 - 2166 (2007/10/02)
Alkylation of the dibutylstannylene derivative of methyl 4,6-O-benzylidene-α-D-glucopyranose 2a with 2-nitrobenzyl bromide gave a mixture of 2-O- and 3-O-(2-nitrobenzyl) derivatives 3b and 4 b in the ratio ca.3:1.Chromatographic separation and removal of the protecting groups gave the title compound 1.Regiospecific synthesis by 2-nitrobenzylation of the monoalcohol 8a was examined but could not be achieved efficiently.Compound 1 was neither a substrate for nor an inhibitor of coupled hexokinase/glucose-6-phosphate dehydrogenase enzyme system.On photolysis, it was converted into free glucose with 1:1 stoichiometry.
SYNTHETIC STUDIES ON NOGALAMYCIN: STEREOSPECIFIC C-5 ALKYLATION OF A SUGAR DERIVATIVE VIA CLAISEN REARRANGEMENT AND A NEW ROUTE TO 1,1,4-TRIALKOXYBUTA-1,3-DIENES.
Vatele, J.-M.
, p. 4443 - 4450 (2007/10/02)
Claisen rearrangement of the 4-methoxybutadienylether of the allylic alcohol 13 which was made in 15 steps from D-glucose, afforded one major aldehyde 17 or 18 in good yield.All attempts to oxidize to an acid were unsuccessful.The model compound 24 and compound 13, were converted respectively to the α, β-unsaturated esters 25 and 26.Compound 25 was further transformed into 1,1,4-trialkoxybuta-1,3-diene 27 which was found unreactive towards quinones.
