GalNAc-β-ONH2 | 390756-34-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GalNAc-β-ONH2
• 英文别名: aminooxy 2-acetamido-2-deoxy-β-D-galactopyranoside；N-[(2S,3R,4R,5R,6R)-2-aminooxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 390756-34-0
• 化学式: C₈H₁₆N₂O₆
• 分子量: 236.225
• InChiKey: XRZLVHCKXHEMGA-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  134
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl fluoride 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 三乙胺 、 甲基肼 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 5.5h， 生成 GalNAc-β-ONH2
  参考文献：
  名称：

  Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates

  摘要：

  Herein, we describe an efficient preparation of various biologically important carbohydrate motifs bearing an aminooxy group at the anomeric position. These nucleophilic sugar analogues represent useful intermediates for the chemoselective preparation of glycoconjugates. The key glycosylation step involves the coupling of fluoro-activated protected sugar and N-hydroxyphthalimide in the presence of BF3. Et2O. Final deprotection and cleavage of the phthalimide moiety with methylhydrazine afforded new Glc-beta -ONH2 3, GalNAc-beta -ONH2 9, Glc-alpha -ONH2 14, Gal-alpha -ONH2 17 and Man-alpha -ONH2 20 derivatives with good yields. Compared to the literature results, the preparation of Gal-beta -ONH2 6, GalNAc-alpha -ONH2 11 and Lac-beta -ONH2 23 proved to be more efficient. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01614-8

文献信息

• METHODS, COMPOSITIONS, AND SYSTEMS FOR DELIVERING THERAPEUTIC AND DIAGNOSTIC AGENTS INTO CELLS
  申请人：PHASERX, INC.

  公开号：US20180221402A1

  公开（公告）日：2018-08-09

  Disclosed are methods for delivering a therapeutic or diagnostic agent to the cytosol of a cell in a subject. The disclosed methods generally include administering to the subject an effective amount of a lipid nanoparticle comprising the therapeutic or diagnostic agent and an effective amount of a membrane-destabilizing polymer. Also disclosed are related compositions and delivery systems.