Antitumor activities of α-, β-monogalactosylceramides and four diastereomers of an α-galactosylceramide

Thermotropic liquid crystalline properties of amphiphilic branched chain glycolipids

“…Glycolipids can be isolated from living materials, such as marine sponges [1], or can be synthesized chemically or enzymatically [2]. Some have immune-stimulating activity, making them candidates for anti-cancer drugs [3]; they play a role in cell fusion [4,5] and in cell surface recognition processes [6].…”

Synthesis of Stable Carbohydrate Mimetics as Potential Glycotherapeutics

“…24 Testing of O-analogs of both the b-and a-anomers showed the same trend. 25 We Ester formation (19 + 20 → 21) proceeded smoothly and application of our three-step protocol (Takai methylenation, RCM with 20 mol% of catalyst 8 and hydroboration; oxidative work-up) afforded the target C-glycoside 23 in 40% yield over three steps (Scheme 3). Benzylation (23 → 24, 98%) was followed by acetonide cleavage, oxidation and Wittig reaction to furnish olefin 25 in 89% yield over 3 steps.…”

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

“…87,88) On the other hand, a 4-deoxy-4,4-difluoro analog, 22, one of the mimics of 21, induced only moderate and slightly Th1-biased cytokine production. 89) According to Fan et al, galactosyl serine analog 23 showed weak bioactivity, and therefore a hydroxy group at the 3-position is preferable as a proton donor to a carbonyl group in making a stable CD1d/ligand complex.…”

“…Prior to the discovery of 1, many mono-and disaccharide analogs of glycosphingolipids had been synthesized and assayed. Koezuka and co-workers investigated immunostimulatory and antitumor activities and the enhancing effects on NK cell activity of many monoglycosyl ceramides, 7,88,100,101) and found that (i) generally, -epimers were bioactive, whereas -ones were almost inactive; (ii) pyranoses were preferable to furanoses; and (iii) among the -D-glycopyranosyl ceramides, an -D-galactose analog and an -D-fucose analog showed the most potent bioactivities. Based on these findings, they concluded that -D-galactopyranoside is the best agent for immunostimulation.…”