2-acetamido-2-deoxy-D-allopyranoside | 72-87-7

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2-deoxy-D-allopyranoside
• 英文别名: 2-acetamido-2-deoxy-D-allose；N-acetyl-D-allosamine；acetyl glucosamine；N-[(3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 72-87-7；1136-42-1；1136-44-3；6082-29-7；6730-06-9；7772-94-3；10036-64-3；14131-60-3；14131-64-7；14131-68-1；14215-68-0；62057-49-2；62057-50-5；62057-51-6；62057-52-7；62057-53-8；62057-54-9；62057-55-0；62057-56-1；62075-50-7；62137-54-6；134451-97-1；134522-12-6；148347-16-4
• 化学式: C₈H₁₅NO₆
• 分子量: 221.21
• InChiKey: OVRNDRQMDRJTHS-IYWGXSQHSA-N

物化性质

• 熔点：
  211 °C
• 沸点：
  595.4±50.0 °C(Predicted)
• 密度：
  1.50
• LogP：
  -2.314 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

制备方法与用途

该化合物2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖主要用于科研。

反应信息

• 作为反应物：
  描述：

  2-acetamido-2-deoxy-D-allopyranoside 在 N-acetylhexosamine-1-kinase 、 adenosine 5’-triphosphate disodium salt hydrate 、 magnesium chloride 作用下， 反应 19.0h， 以22%的产率得到2-acetamido-2-deoxy-α-D-allosyl diammonium phosphate
  参考文献：
  名称：

  A chemoenzymatic route to N-acetylglucosamine-1-phosphate analogues: substrate specificity investigations of N-acetylhexosamine 1-kinase

  摘要：

  报告了一种通过N-乙酰氨基己糖1-激酶（NahK）高效化学酶法生产N-乙酰氨基己糖1-磷酸类似物库的方法，并描述了该酶的相应底物特异性。

  DOI：

  10.1039/b904853g
• 作为产物：
  描述：

  D-GlcNAc 在 盐酸 、 sodium tetrahydroborate 、 [(neocuproine)Pd(μ-OAc)]₂(OTf)₂ 、 silver(I) acetate 、 溶剂黄146 、 对苯醌 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 172.0h， 生成 2-acetamido-2-deoxy-D-allopyranoside
  参考文献：
  名称：

  Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

  摘要：

  Palladium-catalyzed oxidation of isopropyl N-acetyl-alpha-D-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an entry into branching of the carbon skeleton in this compound.

  DOI：

  10.1021/acs.joc.8b01949

文献信息

• PRODUCTION OF OLIGOSACCHARIDE MIXTURES BY A CELL
  申请人：Inbiose N.V.

  公开号：EP3954769A1

  公开（公告）日：2022-02-16

  The present invention is in the technical field of synthetic biology and metabolic engineering. More particularly, the present invention is in the technical field of fermentation of metabolically engineered cells. The present invention provides a method for the production of a mixture of at least two different oligosaccharides by a cell as well as the purification of at least one of said oligosaccharides from the cultivation. In addition, the present invention provides a method for the production of a mixture of at least two different oligosaccharides by a metabolically engineered cell as well as the purification of at least one of said oligosaccharides from the cultivation.

  本发明属于合成生物学和代谢工程技术领域。更具体地说，本发明属于代谢工程细胞发酵技术领域。本发明提供了一种细胞生产至少两种不同低聚糖混合物的方法，以及从培养物中纯化至少一种所述低聚糖的方法。此外，本发明还提供了一种通过代谢工程细胞生产至少两种不同低聚糖混合物以及从培养物中纯化至少一种所述低聚糖的方法。
• PRODUCTION OF A MIXTURE OF NEUTRAL NON-FUCOSYLATED OLIGOSACCHARIDES BY A CELL
  申请人：Inbiose N.V.

  公开号：EP3954778A1

  公开（公告）日：2022-02-16

  The present invention is in the technical field of synthetic biology and metabolic engineering. More particularly, the present invention is in the technical field of fermentation of metabolically engineered cells. The present invention describes a metabolically engineered cell for production of a mixture of at least three different neutral non-fucosylated oligosaccharides. Furthermore, the present invention provides a method for the production of a mixture of at least three different neutral non-fucosylated oligosaccharides by a cell as well as the purification of at least one of said oligosaccharides from the cultivation.

  本发明属于合成生物学和代谢工程技术领域。更具体地说，本发明属于代谢工程细胞发酵技术领域。本发明描述了一种用于生产至少三种不同中性非岩藻糖基化低聚糖混合物的代谢工程细胞。此外，本发明还提供了一种细胞生产至少三种不同的中性非琥珀酰化低聚糖混合物的方法，以及从培养物中纯化至少一种所述低聚糖的方法。
• Design, synthesis and molecular modeling of aloe-emodin derivatives as potent xanthine oxidase inhibitors
  作者：Da-Hua Shi、Wei Huang、Chao Li、Yu-Wei Liu、Shi-Fan Wang

  DOI：10.1016/j.ejmech.2014.01.058

  日期：2014.3

  A series of aloe-emodin derivatives were synthesized and evaluated as xanthine oxidase inhibitors. Among them, four aloe-emodin derivatives showed significant inhibitory activities against xanthine oxidase. The compound 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (A1) possessed the best xanthine oxidase inhibitory activity with IC50 of 2.79 mu M. Lineweaver-Burk plot analysis revealed that A1 acted as a mixed-type inhibitor for xanthine oxidase. The docking study revealed that the molecule A1 had strong interactions with the active site of xanthine oxidase and this result was in agreement with kinetic study. Consequently, compound A1 is a new-type candidate for further development for the treatment of gout. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis of novel disaccharides based on glycosyltransferases: β1,4galactosyltransferase
  作者：Chi-Huey Wong、Thomas Krach、Christine Gautheron-Le Narvor、Yoshitaka Ichikawa、Gary C. Look、Federico Gaeta、David Thompson、K.C. Nicolaou

  DOI：10.1016/s0040-4039(00)93482-8

  日期：1991.9

  Beta-1,4Galactosyltransferase and beta-galactosidase have been investigated with regard to their acceptor specificity and used in the synthesis of galactosides using 5-thioglucose, deoxyazaglucose, glucal, modified N-acetylglucosamine and glucose derivatives as acceptors.
• Jaeger, Volker; Schroeter, Detlef, Synthesis, 1990, # 7, p. 556 - 560
  作者：Jaeger, Volker、Schroeter, Detlef

  DOI：——

  日期：——