138906-42-0Relevant articles and documents
Ionic-liquid supported rapid synthesis of an: N -glycan core pentasaccharide on a 10 g scale
Li, Wei,Gao, Yu,Li, Qing,Li, Zhong-Jun
, p. 4720 - 4727 (2018)
A new and efficient Ionic Liquid-Supported Oligosaccharide Synthesis (ILSOS) strategy for an N-linked core pentasaccharide on a 10 g scale is reported. This new ILSOS includes a new spacer for an IL support, a new tagging strategy, and fast, efficient and orthogonal removal of the ionic-liquid support, producing the N-linked core pentasaccharide with direct applicability potential in a short time, with high yield and on a large gram scale.
Regio/Stereoselective Glycosylation of Diol and Polyol Acceptors in Efficient Synthesis of Neu5Ac-α-2,3-LacNPhth Trisaccharide
Zhang, Ying,Zhao, Fu-Long,Luo, Tao,Pei, Zhichao,Dong, Hai
, p. 223 - 234 (2018/12/05)
A concise approach to a Neu5Ac-α-2,3-LacNPhth trisaccharide derivative was developed. First, the regio/stereoselective glycosylation between glycoside donors and glucoNPhth diol acceptors was investigated. It was found that the regioselectivity depends not only on the steric hindrance of the C2-NPhth group and the C6-OH protecting group of the glucosamine acceptors, but also on the leaving group and protecting group of the glycoside donors. Under optimized conditions, LacNPhth derivatives were synthesized in up to 92 % yield through a regio/stereoselective glycosylation between peracetylated-α-galactopyranosyl trichloroacetimidate and p-methoxyphenyl 6-O-tert-butyldiphenylsilyl-2-deoxy-2-phthalimido-β-d-glucopyranoside, avoiding the formation of glycosylated orthoesters and anomeric aglycon transfer. Then, the LacNPhth derivative was deacylated and then protected on the primary position by TBDPS to form a LacNPhth polyol acceptor. Finally, the Neu5Ac-α-2,3-LacNPhth derivative was synthesized in 48 % yield through the regio/stereoselective glycosylation between the LacNPhth polyol acceptor and a sialyl phosphite donor. Starting from d-glucosamine hydrochloride, the target Neu5Ac-α-2,3-LacNPhth derivative was synthesized in a total yield of 18.5 % over only 10 steps.
Synthesis and immunological characterization of modified hyaluronic acid hexasaccharide conjugates
Gu, Guofeng,Adabala, Pal John Pal,Szczepina, Monica G.,Borrelli, Silvia,Pinto, B. Mario
, p. 8004 - 8019 (2013/09/12)
The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-d-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine ε-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.
Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
Wang, Peng,Wang, Jun,Guo, TianTian,Li, Yingxia
experimental part, p. 607 - 620 (2010/09/20)
Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-β-d-glucosamine, and (1→4)-linked and (1→6)-linked N-acetyl-β-d-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by
Sugars within a hydrophobic scaffold: Glycodendrimers from polyphenylenes
Sakamoto, Junji,Muellen, Klaus
, p. 4277 - 4280 (2007/10/03)
(Chemical Equation Presented) A new glycodendrimer type has been introduced that is designed on the basis of shape-persistent polyphenylene dendrimers. The sugar installation occurs not only on the dendrimer surface but also within the hydrophobic internal scaffold. The synthesis has been accomplished via both convergent and divergent routes by employing the Schmidt glycosylation and the Diels-Alder reaction. This new glycodendrimer has been found to exhibit water-solubility, while conserving hydrophobicity of the interior environment despite the incorporation of sugars.
Synthesis of sulfated glucuronyl glycosphingolipids; carbohydrate epitopes of neural cell-adhesion molecules
Nakano,Ito,Ogawa
, p. 43 - 69 (2007/10/02)
The sulfated glucuronyl glycosphingolipids isolated from the human peripheral nervous system, HO3S-3-β-GlcpA-(1 → 3)-{β-D-Galp-(1 → 4)-β-D-GlcpNAc-(1 → 3)}(n)-β-D-Galp-(1 → 4)-β-D-Glcp-(1 → 1)-Cer (n = 1, 2) (1 and 2) were synthesized. The glyc
Total synthesis of a sulfated glucuronyl glycosphingolipid, IV3GlcA(3-SO3)nLcOse4Cer, a carbohydrate epitope of neural cell adhesion molecules
Nakano, Takahisa,Ito, Yukishige,Ogawa, Tomoya
, p. 1597 - 1600 (2007/10/02)
A total synthesis of a sulfated glucuronyl glycosphingolipid isolated from human peripheral nervous system was achieved for the first time.
