Gal-α-ONH2 | 390756-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal-α-ONH2
• 英文别名: (2R,3R,4S,5R,6R)-2-aminooxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 390756-37-3
• 化学式: C₆H₁₃NO₆
• 分子量: 195.172
• InChiKey: RHMWVNFRRRZAAQ-FPRJBGLDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  125
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-1-oxooctadecan-2-yl)hexacosanamide 、 Gal-α-ONH2 在 盐酸 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 以39%的产率得到O-α-D-galacopyranosyl-(1',1)-(2S,3S,4R)-2-hexacosanoylamino-3,4-bis(tert-butyldimethylsiloxy)octadecanylaldoxime
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045
• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-N-oxysuccinimide 在 肼 作用下， 以 甲醇 为溶剂， 以92%的产率得到Gal-α-ONH2
  参考文献：
  名称：

  Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

  摘要：

  Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.045

文献信息

• Inhibition of Mitosis by Glycopeptide Dendrimer Conjugates of Colchicine
  作者：David Lagnoux、Tamis Darbre、M. Lienhard Schmitz、Jean-Louis Reymond

  DOI：10.1002/chem.200401294

  日期：2005.6.20

  devices for colchicine. Colchicine was attached to the dendrimers at the cysteine thiol group through a disulfide or thioether linkage. The biological activities of the glycopeptide dendrimer conjugates were evaluated in HeLa tumor cells and non-transformed mouse embryonic fibroblasts (MEFs). The concentrations of glycopeptide dendrimer drug conjugates required to achieve inhibition of cell proliferation

  已经制备了糖肽树状聚合物，其表面上带有四个或八个相同的糖苷部分（β-葡萄糖，α-半乳糖，α-N-乙酰基半乳糖或乳糖），分支内的天然氨基酸（Ser，Thr，His，Asp ，Glu，Leu，Val，Phe），2,3-二氨基丙酸作为分支单元，并在核心保留一个半胱氨酸残基。这些树状聚合物已被用作秋水仙碱的药物递送装置。秋水仙碱通过二硫键或硫醚键连接到半胱氨酸硫醇基团的树枝状聚合物上。在HeLa肿瘤细胞和未转化的小鼠胚胎成纤维细胞（MEF）中评估了糖肽树状聚合物结合物的生物学活性。发现通过干扰微管蛋白系统达到抑制细胞增殖所需的糖肽树状聚合物结合物的浓度比秋水仙碱浓度要高（IC50> 1 microM）。另一方面，糖肽树状大分子缀合物抑制HeLa细胞的增殖比MEF的增殖有效20到100倍。相比之下，非糖基化树状大分子和秋水仙碱本身对HeLa细胞的选择性是10倍或更低。
• Multivalent presentation of carbohydrates by 3₁₄-helical peptide templates: synthesis, conformational analysis using CD spectroscopy and saccharide recognition
  作者：Nitin J. Pawar、Ulf Diederichsen、Dilip. D. Dhavale

  DOI：10.1039/c5ob01673h

  日期：——

  A tetrameric glycoconjugate template, SSFT 1, was coupled with a variety of six aminooxy sugars to achieve multivalent glycoconjugates 2–7.

  一个四聚糖结合物模板，SSFT 1，与多种六个氨氧基糖偶联，以实现多价糖结合物2-7。
• Glycolipid derivatives, their preparation and compositions comprising them
  申请人：Merck & Co., Inc.

  公开号：EP0028196A2

  公开（公告）日：1981-05-06

  Immunologic adjuvants are obtained by the synthesis of 6-(5-cholesten-3#-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside and its 6-deoxy-6-oleamido derivative.

  免疫佐剂是通过合成 6-(5-胆甾烯-3#-氧基)己基 6-氨基-6-脱氧-1-硫代-β-D-吡喃半乳糖苷及其 6-脱氧-6-油酰氨基衍生物获得的。
• Synthesis of multitopic neoglycopeptides displaying recognition and detection motifs
  作者：Olivier Renaudet、Pascal Dumy

  DOI：10.1016/j.bmcl.2005.05.072

  日期：2005.8

  We describe herein the synthesis of cyclic decapeptide template displaying clustered carbohydrate recognition motifs and detection agent on spatially separated domains. Such multitopic labeled neoglycopeptides represent attractive tools for binding assays with carbohydrate binding proteins in glycomic research. (c) 2005 Elsevier Ltd. All rights reserved.
• Expedient synthesis of aminooxylated-carbohydrates for chemoselective access of glycoconjugates
  作者：Olivier Renaudet、Pascal Dumy

  DOI：10.1016/s0040-4039(01)01614-8

  日期：2001.10

  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.