63734-12-3Relevant articles and documents
DABCO: An efficient promoter for the acetylation of carbohydrates and other substances under solvent-free conditions
Ch, Ratnasekhar,Tyagi, Mohit,Patil, Premanand Ramrao,Kartha, K.P. Ravindranathan
, p. 5841 - 5846 (2011)
A simple, mild and efficient solvent-free method for the acetylation of carbohydrates, and their partially protected derivatives, as well as non-carbohydrate substances in excellent yields in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) is described with the advantage of tolerance to various functional groups, short reaction time and ease of product isolation.
Effect of solvation on the rotation of hydroxymethyl groups in carbohydrates
Rockwell, Glen D.,Grindley, T. Bruce
, p. 10953 - 10963 (1998)
The solvent dependences of the populations of the hydroxymethyl rotamers of methyl 2,3,4,6-tetra-O-[2H3]-α-D-glucopyranoside (2a) and methyl 2,3,4- tri-O-[2H3]-α-D-glucopyranoside (6) in 10 and 8 solvents, respectively, have been determined by analysis of 3J(H5,H6R) and 3J(H5,H6S) values and by consideration of evidence for hydrogen bonding through infrared spectroscopy and 3J(H,OH) values. The methods used to determine coupling constants in individual hydroxymethyl rotamers were reexamined, and an improved protocol was developed. When 0-6 is methylated (2a), the populations of the hydroxymethyl rotamers are largely independent of solvent polarity at ratios of about 61:38:0 gg:gt:tg, except that a small population (4%) of the tg rotamer appears in the most polar solvents at the expense of the gg rotamer. When 0-6 is unsubstituted (6), there are substantial changes in rotamer population as solvent polarity increases due to loss of intramolecular hydrogen bonding and stabilization of the more polar rotamers. The rotamer populations for 6 return to those adopted by the permethylated derivative (2a) in the most polar solvents. It was concluded that hydrogen bond donation from OH-6 to water is not important in determining hydroxymethyl rotational preferences. The well-known 'reversed' chemical shift order of the two C6 protons of peracetylated glucopyranose derivatives was shown to also occur for permethylated derivatives and is ascribed to solvent effects in addition to anisotropy. The solvent effect on the chemical shift difference is attributed to the fact that one of the two protons stays on the same side of the pyranose ring in the two more populated rotamers while the other proton exchanges environments.
Catalytic Site-Selective Carbamoylation of Pyranosides
Alsarraf, Jér?me,Petitpoisson, Lucas,Pichette, André
supporting information, p. 6052 - 6056 (2021/08/03)
Carbamate-bearing carbohydrates contribute to the pharmacological properties of various natural glycosides. The catalytic site-selective carbamoylation of minimally protected pyranosides was achieved for the first time to bypass protection/deprotection sequences. 1-Carbamoylimidazoles were used as the carbamoylation reagents to circumvent the harmful and unstable phosgene and isocyanates. This borinic acid catalyzed transformation granted an expedient access to the tumor cell-binding carbamoylmannoside moiety of bleomycins and analogs in yields of 56% to 89%.
Addressing the biochemical foundations of a glucose-based "trojan horse"-strategy to boron neutron capture therapy: From chemical synthesis to in vitro assessment
Ekholm, Filip S.,Matovic, Jelena,Jarvinen, Juulia,Bland, Helena C.,Sokka, Iris K.,Imlimthan, Surachet,Huttunen, Kristiina M.,Timonen, Juri,Peraniemi, Sirpa,Aitio, Olli,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko
, p. 3885 - 3899 (2020/11/12)
Boron neutron capture therapy (BNCT) for cancer is on the rise worldwide due to recent developments of in-hospital neutron accelerators which are expected to revolutionize patient treatments. There is an urgent need for improved boron delivery agents, and herein we have focused on studying the biochemical foundations upon which a successful GLUT1-targeting strategy to BNCT could be based. By combining synthesis and molecular modeling with affinity and cytotoxicity studies, we unravel the mechanisms behind the considerable potential of appropriately designed glucoconjugates as boron delivery agents for BNCT. In addition to addressing the biochemical premises of the approach in detail, we report on a hit glucoconjugate which displays good cytocompatibility, aqueous solubility, high transporter affinity, and, crucially, an exceptional boron delivery capacity in the in vitro assessment thereby pointing toward the significant potential embedded in this approach.
