13089-21-9Relevant articles and documents
Aromatic crown ethers as phase transfer catalysts in the synthesis of N-acetylglucosamine β-aryl glycosides
Chupakhina,Kur'yanov,Chirva,Grigorash,Kotlyar,Kamalov
, p. 301 - 303 (2004)
The crown ether-catalyzed glycosylation of phenol, 4-methoxyphenol, and 4-nitrophenol was studied under phase transfer conditions in solid-liquid system. The asymmetric dibenzocrown esters are superior to [3.3]dibenzo-18- crown-6 and 15-crown-5 in the cat
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Shafizadeh et al.
, p. 1190,1191 (1973)
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Chemical synthesis of 4-azido-β-galactosamine derivatives for inhibitors of N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase
Hor, Seanghai,Kodama, Takumi,Sugiura, Nobuo,Kondou, Hikaru,Yanagida, Mio,Yanagisawa, Keiya,Shibasawa, Aoki,Tsuzuki, Bunta,Fukatsu, Naoto,Nagao, Kazuya,Yamana, Kenji,Hidari, Kazuya I. P. J.,Watanabe, Hideto,Habuchi, Osami,Nakano, Hirofumi
, p. 477 - 491 (2018/09/20)
Chondroitin sulfate E (CS-E) plays a crucial role in diverse processes ranging from viral infection to neuroregeneration. Its regiospecific sulfation pattern, generated by N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase (GalNAc4S-6ST), is the main structural determinant of its biological activity. Inhibitors of GalNAc4S-6ST can serve as powerful tools for understanding physiological functions of CS-E and its potential therapeutic leads for human diseases. A family of new 4-acylamino-β-GalNAc derivatives and 4-azido-β-GalNAc derivatives were synthesized for their potential application as inhibitors of GalNAc4S-6ST. The target compounds were evaluated for their inhibitory activities against GalNAc4S-6ST. The results revealed that 4-pivaloylamino- and 4-azido-β-GalNAc derivatives displayed evident activities against GalNAc4S-6ST with IC50 value ranging from 0.800 to 0.828?mM. They showed higher activities than benzyl D-GalNAc4S that was used as control.
Hydration of Sugars in the gas phase: Regioselectivity and conformational choice in N-acetyl glucosamine and glucose
Cocinero, Emilio J.,Stanca-Kaposta, E. Cristina,Dethlefsen, Mark,Liu, Bo,Gamblin, David P.,Davis, Benjamin G.,Simons, John P.
supporting information; experimental part, p. 13427 - 13434 (2010/04/30)
The influence of an acetamido group in directing the preferred choice of hydration sites in glucosamine and a consequent extension of the working rules governing regioselective hydration and conformational choice, have been revealed through comparisons between the conformations and structures of "free" and multiply hydrated phenyl N-acetyl-β-D-glucosamine (sβpGlcNAc) and phenyl β-D-glucopyranoside (βpGlc), isolated in the gas phase at low temperatures. The structures have been assigned through infrared ion depletion spectroscopy conducted in a supersonic jet expansion, coupled with computational methods. The acetamido motif provides a hydration focus that overwhelms the directing role of the hydroxymethyl group; in multiply hydrated βpGlcNAc the water molecules are all located around the acetamido motif, on the "axial" faces of the pyranose ring rather than around its edge, despite the equatorial disposition of all the hydrophilic groups in the ring. The striking and unprecedented role of the C-2 acetamido group in controlling hydration structures may, in part, explain the differing and widespread roles of GlcNAc, and perhaps GalNAc, in nature.
