90-76-6Relevant articles and documents
Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization-tandem mass spectrometry: Evidence and tags to distinguish different glycosaminoglycans
Zhu, He,Chen, Xuan,Zhang, Xiao,Liu, Lili,Cong, Dapeng,Zhao, Xia,Yu, Guangli
, p. 63 - 69 (2015/02/18)
Diverse monosaccharide analysis methods have been established for a long time, but few methods are available for a complete monosaccharide analysis of glycosaminoglycans (GAGs) and certain acidolysis- resistant components derived from GAGs. In this report, a reversed-phase high-performance liquid chromatography (RP-HPLC) method with pre-column 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization was established for a complete monosaccharide analysis of GAGs. Good separation of glucosamine/ mannosamine (GlcN/ManN) and glucuronic acid/iduronic acid (GlcA/IdoA) was achieved. This method can also be applied to analyze the acidolysis-resistant disaccharides derived from GAGs, and the sequences of these disaccharides were confirmed by electrospray ionization-collision-induced dissociation- tandem mass spectrometry (ESI-CID-MS/MS). These unique disaccharides could be used as markers to distinguish heparin/heparan sulfate (HP/HS), chondroitin sulfate/dermatan sulfate (CS/DS), and hyaluronic acid (HA).
Anti-hepatitis b virus norbisabolane sesquiterpenoids from phyllanthus acidus and the establishment of their absolute configurations using theoretical calculations
Lv, Jun-Jiang,Yu, Shan,Wang, Ya-Feng,Wang, Dong,Zhu, Hong-Tao,Cheng, Rong-Rong,Yang, Chong-Ren,Xu, Min,Zhang, Ying-Jun
, p. 5432 - 5447 (2014/07/08)
Nineteen new highly oxygenated norbisabolane sesquiterpenoids, phyllanthacidoid acid methyl ester (1), and C-T (4-21), were isolated from Phyllanthus acidus Skeels, together with two known ones, phyllanthusols A (2) and B (3), whose sugar moiety was revised as glucosamine-N-acetate, rather than the previously assigned mannosamine-N-acetate. Compounds 2 and 3 were renamed respectively as phyllanthacidoids A (2) and B (3) to avoid confusion. All of the isolates except for 1 are glycosides, whose saccharide moieties possess a pentaoxy cyclohexane (scyllo quercitol) connecting with glucosamine-N-acetate or glucosyl moieties, which are first examples in natural products. Phyllanthacidoids N-R (15-19) with 8R configurations and/or 5,8-diketal skeleton, are unprecedented structures among norbisabolane sesquiterpenoids. Phyllanthacidoids S (20) and T (21) have the unusual tricyclo [3.1.1.1] oxygen bridge skeleton formed by a diketal system, of which the relative configurations of the aliphatic chain were assigned on the basis of heteronuclear coupling constants. The absolute configurations of compounds (1-21) were established by means of calculated electronic circular dichroism (ECD) and coupling constants. Compounds 1-5, 7-9, 10, and 14 displayed potential anti-hepatitis B virus (HBV) activities, with IC50 values of 0.8-36 μM against HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg), and the results indicated that the 5-ketal group and sugar moieties had contributions to the selectivity of HBsAg and HBeAg.
4,6-dimethoxy-1,3,5-triazin-2-yl-d-glycosaminides: Novel substrates for transglycosylation reaction catalyzed by exo-d-glucosaminidase from amycolatopsis orientalis
Tanaka, Tomonari,Wada, Tomonori,Noguchi, Masato,Ishihara, Masaki,Kobayashi, Atsushi,Ohnuma, Takayuki,Fukamizo, Tamo,Brzezinski, Ryszard,Shoda, Shin-Ichiro
, p. 634 - 646 (2013/01/16)
A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl-d-glucosaminide (GlcN-DMT), has been prepared by the reaction of d-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-d-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to d-galactosamine (GalN). GalN-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.
