ethyl 3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside | 149713-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside
• 英文别名: GlcNAc(b1-3)[GlcNAc(b1-6)]Gal(b)-O-Et；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4S,5R,6R)-4-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-ethoxy-3,5-dihydroxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 149713-20-2
• 化学式: C₂₄H₄₂N₂O₁₆
• 分子量: 614.601
• InChiKey: XQIMCOOMYOWPRC-MGRJQWATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  ethyl 3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside 、 uridine 5'-diphospho-β-D-galactose 在 β-1,4-galactosyltransferase (E₁) 作用下， 以93%的产率得到ethyl 3,6-bis-O-<β-D-galactopyranosyl-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranosyl>-β-D-galactopyranoside
  参考文献：
  名称：

  Ligand recognition by E-selectin: analysis of conformation and activity of synthetic monomeric and bivalent sialyl Lewis X analogs

  摘要：

  DOI：

  10.1021/ja00069a083
• 作为产物：
  描述：

  ethyl 3,6-bis-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranosyl)-2,4-di-O-acetyl-β-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以70%的产率得到ethyl 3,6-bis-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Ligand Recognition by E-Selectin: Synthesis, Inhibitory Activity and Conformational Analysis of Bivalent Sialyl Lewis x Analogs

  摘要：

  Several sialyl Lewis x dimers anchored onto a galactose template or attached to 1,4-butanediol or 1,5-pentanediol have been prepared chemoenzymatically and evaluated as inhibitors of E-selectin-mediated cell adhesion. Two monosaccharide units were simultaneously incorporated (i.e., Gal, NeuAc, Fuc) by a glycosyltransferase into a chemically synthesized core structure containing GlcNAc and Gal. Each of the galactose-anchored dimers had higher activity than the sialyl Lewis x pentasaccharide la, with the general trend being 3,6-linked > 2,3 greater than or equal to 4,6 greater than or equal to 2,6 monomer. The dimers linked to butanediol or pentanediol showed the same level of activity as the pentasaccharide monomer. Conformational analysis of these dimers with NMR indicated that each sialyl Lewis x domain of the dimers retains the same conformation as the monomer. The differences in activity of the dimers most likely derive from differences in the relative orientation and distance between the monomer domains, suggesting the importance of the linker used in the preparation of dimers.

  DOI：

  10.1021/ja00106a008

文献信息

• US5559103A
  申请人：——

  公开号：US5559103A

  公开（公告）日：1996-09-24
• [EN] BIVALENT SIALYL LEWIS X SACCHARIDES<br/>[FR] SACCHARIDES SIALYLE LEWIS X BIVALENTS
  申请人：CYTEL CORPORATION

  公开号：WO1995003059A1

  公开（公告）日：1995-02-02

  (EN) The invention relates to bivalent sialyl lewis X saccharide compounds that inhibit cellular binding to a selectin receptor. Pharmaceutical compositions comprising the compound of Formula (I) and processes for making and using the same are also disclosed. The compound has the following substituents: R is a divalent monosaccharide unit; Y is selected from the group consisting of C(O), SO2, HNC(O) and SC(O); R2 is selected from the group consisting of C1-C6 hydrocarbyl, phenyl C1-C3 alkylene, an aryl which may be further substituted with a halo, trifluoromethyl, nitro, C1-C6 alkyl, alkoxy, amino, alkylamino, and benzylamino; R3 is methyl or hydroxymethyl; X is hydroxyl, acyloxy, hydroxyacyloxy, halo and azido; Z1 and Z2 are fucosyl or H, and M is a cation.(FR) Cette invention concerne des composés bivalents saccharides sialyle lewis X qui inhibent la liaison cellulaire avec un récepteur de sélectine; ainsi que des compositions pharmaceutiques renfermant le composé de formule (I) et des procédés de préparation et d'utilisation de ce dernier. Le composé comprend les substituants suivants: R représente une unité monosaccharide bivalente; Y est sélectionné dans le groupe formé par C(O), SO2, HNC(O) et SC(O); R2 est sélectionné dans le groupe constitué par C1-C6 hydrocarbyle, phényle C1-C3 alkylène, aryle pouvant être substitué par halo, trifluorométhyle, nitro, C1-C6 alkyle, alcoxy, amino, alkylamino et benzylamino; R3 représente méthyle ou hydroxyméthyle; X représente hydroxyle, acyloxy, hydroxyacyloxy, halo et azido; Z1 et Z2 représente fucosyle ou H, et M représente un cation.