2771-55-3Relevant academic research and scientific papers
Immobilization of UDP-Galactose on an Amphiphilic Resin
Bevan, Jessica G. M.,Louren?o, Eva C.,Chaves-Ferreira, Miguel,Rodrigues, Jo?o A.,Rita Ventura
supporting information, p. 908 - 914 (2018/02/27)
Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin-bound nucleotide sugars: fluorinated UDP-galactose and UDP-galactose. They were conjugated to a polyethylene glycol resin through the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin-bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry-based screening system for enzymes that use UDP-galactose.
Synthesis and biological activity of hydroxylated analogues of KRN7000 (α-galactosylceramide)
Shiozaki, Masao,Tashiro, Takuya,Koshino, Hiroyuki,Shigeura, Tomokuni,Watarai, Hiroshi,Taniguchi, Masaru,Mori, Kenji
, p. 46 - 66 (2013/04/23)
KRN7000 is one of the α-galactosylceramides, which has a 2-hexacosanoylamino-3,4-dihydroxyoctadecyl group. This compound, known as a ligand for the activation of CD1d mediated invariant natural killer T cells (iNKT cells) which release both T helper 1 (Th
Impact of sugar stereochemistry on natural killer T cell stimulation by bacterial glycolipids
Deng, Shenglou,Mattner, Jochen,Zang, Zhuo,Bai, Li,Teyton, Luc,Bendelac, Albert,Savage, Paul B.
supporting information; experimental part, p. 7659 - 7662 (2011/12/04)
Natural killer T (NKT) cells recognize glycolipids produced by Sphingomonas bacteria, and these glycolipids contain C6-oxidized sugars, either glucuronic acid or galacturonic acid, linked to ceramides. Glycolipids with gluco stereochemistry are the most p
Divergent synthesis of L-sugars and L-iminosugars from D-sugars
Takahashi, Hideyo,Shida, Tomomi,Hitomi, Yuko,Iwai, Yoshinori,Miyama, Namisa,Nishiyama, Kazusa,Sawada, Daisuke,Ikegami, Shiro
, p. 5868 - 5877 (2008/03/11)
An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxim
Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
Namme, Rie,Mitsugi, Takashi,Takahashi, Hideyo,Shiro, Moto,Ikegami, Shiro
, p. 9183 - 9192 (2007/10/03)
A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely α-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by 3JC,H coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective.
Total synthesis of arthrobacilin A
Garcia, Dulce M.,Yamada, Hidetoshi,Hatakeyama, Susumi,Nishizawa, Mugio
, p. 3325 - 3328 (2007/10/02)
Novel cyclic glycolipids, arthrobacilin A and its analogues, have been synthesized by means of unique DCC/DMAP·HCl promoted oligomerization/cyclization, zinc salt catalyzed β-selective glycosylation, and Noyori's BINAP/Ru catalyzed asymmetric reduction.
SYNTHESIS OF DERMATAN SULFATE FRAGMENTS: A CHEMICAL SYNTHESIS OF METHYL 2-ACETAMIDO-2-DEOXY-3-O-(α-L-IDOPYRANOSYLURONIC ACID)-4-O-SULFO-β-D-GALACTOPYRANOSIDE DISODIUM SALT AND ITS NON-SULFATED ANALOGUE
Jacquinet, Jean-Claude,Sinay, Pierre
, p. 229 - 254 (2007/10/02)
Methyl 2-azido-2-deoxy-β-D-galactopyranoside was subjected in sequence to isopropylidenation, benzylation, acid hydrolysis, and selective acetylation of HO-4, to give amorphous methyl 4-O-acetyl-2-azido-6-O-benzyl-2-deoxy-β-D-galactopyranoside.Condensatio
