2-acetamido-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine | 73982-39-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine
• 英文别名: 2-acetamido-2-deoxy-1-N-chloroacetyl-β-D-glucopyranosylamine；N-chloroacetyl-2-acetamido-2-deoxy-β-D-glucopyranosylamine；N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)chloroacetamide；2-acetamido-N-chloroacetyl-2-deoxy-β-D-glucopyranosylamine；N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-chloroacetamide
• CAS: 73982-39-5
• 化学式: C₁₀H₁₇ClN₂O₆
• 分子量: 296.708
• InChiKey: HBWYPXIWWYDJDZ-QXOHVQIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  128
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-acetamido-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine 在 sodium azide 、 Na β-zeolite 作用下， 以 水 、 丙酮 为溶剂， 反应 36.0h， 生成 N-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-β-D-gluco-pyranosyl)azidoacetamide
  参考文献：
  名称：

  Synthesis ofN‐(β‐Glycopyrano‐syl)azidoacetamides

  摘要：

  N-(beta-Glycopyranosyl)azidoacetamides, mimetics of the widely distributed GlcNAc-Asn linkage in glycoproteins, have been synthesized in good yields starting from beta-glycopyranosylamines in four steps involving selective N-chloroacetylation, peracetylation catalyzed by Na beta-zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de-O-acetylation.

  DOI：

  10.1081/car-200049402
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-3,4,6-三-邻乙酰基-beta-d-吡喃葡萄糖胺 在 三乙胺 作用下， 以 吡啶 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成 2-acetamido-1-N-(chloroacetyl)-2-deoxy-β-D-glucopyranosylamine
  参考文献：
  名称：

  一些1-N-取代的2-乙酰氨基-2-脱氧-β-D-甘露糖基糖胺衍生物和相关类似物的合成和生物活性。

  摘要：

  2-乙酰氨基-2-脱氧-3,4,6-三-O的几种1-N-取代的衍生物[卤代乙酰基，甘氨酰-，（二甲基）氨基-乙酰基，叠氮基乙酰基，三氟乙酰基和三氟甲基磺酰基-] -乙酰基-β-D-吡喃葡萄糖胺（1）被合成为细胞膜糖缀合物的潜在代谢抑制剂。在体外浓度为1-0.01 mM时，发现几种完全乙酰化的衍生物可以抑制小鼠乳腺腺癌TA3，白血病L1210或白血病P-288细胞的生长。这些衍生物中的一些在O-脱乙酰基之后活性较低。其中NH2-1被OH-或OAc-1取代的类似物1在相同的电池系统上也很活跃。生长抑制活性与2-氨基-脱氧-D-葡萄糖和L-亮氨酸掺入大分子级分的抑制有关。

  DOI：

  10.1016/s0008-6215(00)85318-5

文献信息

• Glycoconjugates of amino acids. Preparation throughN-alkylation of amino acids withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02495306

  日期：1999.7

  Monoalkylation of amino acids of different structural types withN-chloroacetyl-glycosylamines was shown to be applicable for the preparation of glycoconjugates containing β-d-galactose,N-acetyl-β-d-glucosamine, β-d-mannose, and lactose residues. The glycoconjugates were synthesized from amino acids with secondary (sarcosine,l-proline) or primary (l-2- and 4-aminobutyric acids,l-tryptophan) amino groups

  不同结构类型的氨基酸与 N-氯乙酰-糖胺的单烷基化被证明适用于制备含有 β-d-半乳糖、N-乙酰-β-d-葡糖胺、β-d-甘露糖和乳糖残基的糖缀合物。糖缀合物由具有二级（肌氨酸，l-脯氨酸）或一级（l-2-和4-氨基丁酸，l-色氨酸）氨基的氨基酸以及各种氨基二羧酸（N-甲基-dl-天冬氨酸、dl-天冬氨酸、l-谷氨酸和dl-2-氨基己二酸）。获得的衍生物可能对本系列生理活性化合物的糖靶向作用感兴趣。
• N-glycyl-β-glycopyranosylamines, derivatives of mono- and disaccharides, and their use for the preparation of carboxylic acid glycoconjugates
  作者：L. M. Likhosherstov、O. S. Novikova、A. O. Zheltova、V. N. Shibaev

  DOI：10.1007/bf02495096

  日期：2000.8

  ofN-glycyl-β-glycopyranosylamines, derivatives of monosaccharides (d-galactose,d-mannose,l-fucose, andN-acetyl-d-glucosamine) and disaccharides (lactose, melibiose, cellobiose, and maltose). These compounds were demonstrated to be useful for the preparation of glycoconjugates of biologically active compounds containing the carboxy group (nicotinic, orotic, kynurenic, and indoleacetic acids). Synthetic pathways

  为合成 N-甘氨酰-β-吡喃葡萄糖胺、单糖衍生物（d-半乳糖、d-甘露糖、l-岩藻糖和 N-乙酰-d-葡糖胺）和二糖（乳糖、蜜二糖、纤维二糖、和麦芽糖）。这些化合物被证明可用于制备含有羧基的生物活性化合物（烟碱酸、乳清酸、犬尿酸和吲哚乙酸）的糖缀合物。开发了使用丙二酸和l-酒石酸衍生物将N-甘氨酰-β-吡喃葡萄糖胺转化为含有羧基的衍生物的合成途径。
• Glycoconjugates of amines: alkylation of primary and secondary amines withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02503499

  日期：1998.6

  Efficient monoalkylation of a series of primary and secondary amines was demonstrated with the use ofN-chloroacetylglycosylamines derived fromd-glucose,d-galactose,d-mannose,N-acetyl-d-glucosamine, and lactose. The reaction was shown to be useful for incorporation of carbohydrate residues into physiologically active compounds. Glycoconjugates of some derivatives of piperazine, 2-phenylethylamine, tryptamine

  使用衍生自 d-葡萄糖、d-半乳糖、d-甘露糖、N-乙酰基-d-葡糖胺和乳糖的 N-氯乙酰基糖胺证明了一系列伯胺和仲胺的有效单烷基化。该反应被证明可用于将碳水化合物残基结合到生理活性化合物中。制备了哌嗪、2-苯乙胺、色胺和重要生物胺（去甲麻黄碱、章鱼胺、多巴胺）的一些衍生物的糖缀合物。
• Synthesis ofN4-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues
  作者：Jayshri J. Malik、John M. Risley

  DOI：10.1002/1097-458x(200102)39:2<98::aid-mrc792>3.0.co;2-3

  日期：2001.2

  N-4-(2-Acetamido-2-deoxy-beta -D-glucopyranosyl)-L-aspargine is the principle linkage in the structure of N-linked glycoproteins. Complete assignments of the H-1 and C-13 NMR spectra for three analogues of the naturally-occurring N-glycosylic structure were made for N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)chloroacetamide, N-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)bromacetamide and N-1-(2-acetamido-2-deoxy-beta -D-glucopyranosyl)glycinamide. The methylene groups adjacent to the N-glycosylic bond are AB spin systems. Copyright (C) 2001 John Wiley & Sons, Ltd.
• Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-β-d-glycopyranosylamine derivatives and related analogs
  作者：Brajeswar Paul、Ralph J. Bernacki、Walter Korytnyk

  DOI：10.1016/s0008-6215(00)85318-5

  日期：——

  adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction

  2-乙酰氨基-2-脱氧-3,4,6-三-O的几种1-N-取代的衍生物[卤代乙酰基，甘氨酰-，（二甲基）氨基-乙酰基，叠氮基乙酰基，三氟乙酰基和三氟甲基磺酰基-] -乙酰基-β-D-吡喃葡萄糖胺（1）被合成为细胞膜糖缀合物的潜在代谢抑制剂。在体外浓度为1-0.01 mM时，发现几种完全乙酰化的衍生物可以抑制小鼠乳腺腺癌TA3，白血病L1210或白血病P-288细胞的生长。这些衍生物中的一些在O-脱乙酰基之后活性较低。其中NH2-1被OH-或OAc-1取代的类似物1在相同的电池系统上也很活跃。生长抑制活性与2-氨基-脱氧-D-葡萄糖和L-亮氨酸掺入大分子级分的抑制有关。