(2S,5R,6R)-3,3-二甲基-7-羰基-6-{[(三氟甲基)磺酰]氨基}-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸4,4-二氧化 | 73982-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (2S,5R,6R)-3,3-二甲基-7-羰基-6-{[(三氟甲基)磺酰]氨基}-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸4,4-二氧化
• 英文名称: 2-acetamido-N-bromoacetyl-2-deoxy-β-D-glucopyranosylamine
• 英文别名: N-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-2-bromoacetamide
• CAS: 73982-43-1
• 化学式: C₁₀H₁₇BrN₂O₆
• 分子量: 341.159
• InChiKey: SEWSVWXDUATJEE-QXOHVQIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 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：

  (2S,5R,6R)-3,3-二甲基-7-羰基-6-{[(三氟甲基)磺酰]氨基}-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸4,4-二氧化 在 ammonium carbonate 作用下， 生成 N-(2-acetamido-2-deoxy-β-D-glucopyranosyl)glycinamide
  参考文献：
  名称：

  Synthesis ofN4-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues

  摘要：

  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.

  DOI：

  10.1002/1097-458x(200102)39:2<98::aid-mrc792>3.0.co;2-3
• 作为产物：
  描述：

  D-GlcNAc 在 碳酸氢铵 作用下， 以 二甲基亚砜 为溶剂， 生成 (2S,5R,6R)-3,3-二甲基-7-羰基-6-{[(三氟甲基)磺酰]氨基}-4-硫杂-1-氮杂二环[3.2.0]庚烷-2-羧酸4,4-二氧化
  参考文献：
  名称：

  Synthesis ofN4-(2-acetamido-2-deoxy-?-D-glucopyranosyl)-L-asparagine analogues. Complete NMR assignments of chloroacetamide, bromoacetamide and glycinamide analogues

  摘要：

  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.

  DOI：

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

文献信息

• 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。
• Spontaneously Cleavable Glycosylated Linker Capable of Extended Release of Its Conjugated Peptide
  作者：Hirofumi Ochiai、Kenta Yoshida、Hiroshi Shibutani、Akio Kanatani、Yuji Nishiuchi

  DOI：10.1248/cpb.c18-00626

  日期：2019.3.1

  the aim of increasing the solubility and stability of the peptides in plasma. The amino or carboxyl group of the peptide was connected to a glycosylated Ascendis or ester/thioester-type linker, respectively. Use of the linkers enabled extended release of the peptides depending on the pH and temperature of the buffer according to a first order reaction, and their cleavage rate was also affected by the

  可逆糖基化偶联物的开发是通过将自肽型连接子添加复杂型的N-连接寡糖添加到肽中来实现的，目的是增加肽在血浆中的溶解度和稳定性。肽的氨基或羧基分别连接到糖基化的Ascendis或酯/硫酯型接头上。接头的使用使得能够根据一级反应根据缓冲液的pH和温度来延长肽的释放，并且它们的裂解速率也受到肽-接头偶联结构的影响。这种可调性将允许针对要释放的肽的预期用途进行优化。此外，由于糖基化是一种大大提高肽段溶解度的可靠方法，
• An improved procedure for the synthesis of N-bromoacetyl- -glycopyranosylamines, derivatives of mono- and disaccharides
  作者：L. M. Likhosherstov、O. S. Novikova、A. O. Zheltova、V. N. Shibaev

  DOI：10.1023/b:rucb.0000035661.45796.f7

  日期：2004.3

  An improved procedure for the synthesis of N-bromoacetyl-β-glycopyranosylamines from the corresponding β-glycosylamines was developed. The procedure is applicable to a wide range of derivatives of monosaccharides (hexoses, 2-acetamido-2-deoxyhexoses, hexuronamides, and 6-deoxyhexoses) and some disaccharides. For the derivatives of pentoses and 2-deoxyhexoses, the use of the corresponding β-glycosylammonium

  开发了一种从相应的 β-糖基胺合成 N-溴乙酰基-β-吡喃葡萄糖胺的改进方法。该程序适用于广泛的单糖衍生物（己糖、2-乙酰氨基-2-脱氧己糖、己糖醛酰胺和 6-脱氧己糖）和一些二糖。对于戊糖和2-脱氧己糖的衍生物，发现使用相应的β-糖基氨基甲酸铵更方便。首次获得了衍生自 D-甘露糖、L-鼠李糖、D-葡萄糖醛酸酰胺、2-脱氧-D-阿拉伯己糖、2-脱氧-D-lyxo-己糖和蜜二糖的 N-溴乙酰-β-吡喃葡萄糖胺。
• N-Bromoacetyl-β-D-glycopyranosylamines in the synthesis of glycoconjugates of nitrogen-containing physiologically active compounds
  作者：L. M. Likhosherstov、O. S. Novikova、A. O. Zheltova、V. N. Shibaev

  DOI：10.1007/s11172-005-0397-y

  日期：2005.5

  smooth N-monoalkylation with N-bromoacetyl-β-glycopyranosylamines derived from N-acetyl-D-glucosamine and lactose. This reaction was demonstrated to be promising for the introduction of carbohydrate residues into heterocyclic compounds, viz., pyridine, imidazole, pyrimidinetrione, carboline, and piperazine derivatives, and into an amino acid, 5-hydroxy-L-tryptophan, which is unstable in alkaline media

  一系列含氮生理活性化合物与衍生自 N-乙酰基-D-葡糖胺和乳糖的 N-溴乙酰基-β-吡喃葡萄糖胺进行平滑的 N-单烷基化。该反应被证明有希望将碳水化合物残基引入杂环化合物中，即吡啶、咪唑、嘧啶三酮、咔啉和哌嗪衍生物，并引入氨基酸，5-羟基-L-色氨酸，在碱性介质。
• Chemoselective Elaboration of <i>O</i>-Linked Glycopeptide Mimetics by Alkylation of 3-ThioGalNAc
  作者：Lisa A. Marcaurelle、Carolyn R. Bertozzi

  DOI：10.1021/ja003713q

  日期：2001.2.1

  A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. We report here a strategy for the synthesis of O-linked glycopeptide analogues that replaces this linkage with a thioether amenable to construction by chemoselective ligation. The key building block was a 2-azido-3-thiogalactose-Thr analogue that was

  粘蛋白型寡糖的一个关键分支点是与核心 α-N-乙酰半乳糖胺 (GalNAc) 残基相连的 β 1--> 3 糖苷键。我们在此报告了一种合成 O 连接糖肽类似物的策略，该策略用适合通过化学选择性连接构建的硫醚取代了这种连接。关键构建块是 2-叠氮基-3-硫代半乳糖-Thr 类似物，它通过基于芴基甲氧基羰基 (Fmoc) 的固相肽合成掺入肽中。高级寡糖很容易通过相应的 3-thioGalNAc 与 N-溴乙酰胺糖的烷基化产生。“核心1”和“核心3”O-连接糖肽模拟物的快速组装以这种方式完成。