Facile synthesis of 4-O-β-N-acetylchitooligosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone based on the transformation of chitooligosaccharide and its suppressive effects against the furylfuramide-induced SOS response.
A facile synthesis method is described for transforming the reducing-end residue of chitooligosaccharides (DP 2-4) into lactone. The desired 4-O-β-N-acetylchitooligosyl lactones (GN(n)L) were conveniently prepared from chitooligosaccharides by consecutive dehydration and oxidation reactions to afford 4-O-β-tri-N-acetylchitotriosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone (GN(3)L), 4-O-β-di-N-acetylchitobiosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone (GN(2)L), and 4-O-β-2-acetamido-2-deoxy-D-glucopyranosyl 2-acetamido-2,3-dideoxydidehydro-gluconolactone (GNL). The resulting lactone derivatives exhibited considerable suppression (42.6-54.3% at a concentration of 400 µM) in umu gene expression of the SOS response in Salmonella typhimurium TA1535/pSK1002 against the mutagen, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamido (AF-2). Lactonization of the chitooligosaccharides was found to be essential for their suppression of the SOS-inducing activity.
Department of Bioscience, Graduate School of Science and Technology, Shizuoka University, Shizuoka, Japan. usui@ipc.shizuoka.ac.jp
Makoto
M
Ogata
Ryota
R
Takeuchi
Akari
A
Suzuki
Hirofumi
H
Hirai
Taichi
T
Usui
D016587:Antimutagenic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002686:Chitin / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D005668:Furylfuramide / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D009153:Mutagens / Q000494:pharmacology*; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D013014:SOS Response, Genetics / Q000187:drug effects; D012486:Salmonella typhimurium / Q000187:drug effects* / Q000254:growth & development
D016587:Antimutagenic Agents; D009153:Mutagens; D009844:Oligosaccharides; D005668:Furylfuramide; D002686:Chitin