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

Non-catalytic dehydration of N,N′-diacetylchitobiose in high-temperature water

“…Chromogen III were synthesized by methods reported previously 8,20 and used as standard samples for HPLC analysis.…”

“…Ogata et al have reported the conversion of (GlcNAc)2 into its dehydration products by incubation in sodium borate solution at 100ºC for 2 hours, obtaining GND in 13% yield. 8 They also reported that GND was easily oxidized to GNL over charcoal catalyst at 60ºC for 120 hours. This previous study found that the dehydration of (GlcNAc)2 requires a catalyst (sodium borate) at temperatures below 100ºC.…”

“…[5][6][7] In addition, transformation of chitin and its oligosaccharides into derivatives has recently been studied to obtain renewable N-containing compounds. [8][9][10][11] medicine. 8 For example, GND is expected as an antioxidant and GNL has been found to exhibit antimutagenic activity.…”

“…[8][9][10][11] medicine. 8 For example, GND is expected as an antioxidant and GNL has been found to exhibit antimutagenic activity. 8 So far, these (GlcNAc)2 derivatives are not commercially available from chemical reagent companies because their syntheses generally involve multi-step pathways, but, their market could be increased if a simple synthesis of (GlcNAc)2 derivatives was developed.…”

A Novel Transition-state Analogue for Lysozyme, 4-O-β-Tri-N-acetylchitotriosyl Moranoline, Provided Evidence Supporting the Covalent Glycosyl-enzyme Intermediate*

“…1) were prepared by our previously described methods (11). (GlcNAc) n (n ϭ 2, 3, 4, and 6) and (GlcNAc) 5 -␤-pNP were kindly provided by Yaizu Suisan Kagaku Industry Co., Ltd. (Shizuoka, Japan).…”