2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside
• 英文别名: N-acetyl-4-deoxy-4-fluoro-D-mannosamine；N-[(3S,4R,5S,6R)-5-fluoro-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₈H₁₄FNO₅
• 分子量: 223.201
• InChiKey: QAPRNMNSFDDVPY-WZPXOXCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 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：
  99
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside 在 Lindlar catalyst sodium azide 、 N-acetylneuraminic acid aldolase 、 Dowex 50W (H+) 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 5-acetamido-4-(N,N'-bis-t-butoxycarbonylguanidino)-8,9-di-O-acetyl-2,3,4,5,7-pentadeoxy-7-fluoro-D-glycero-D-galacto-non-2-enopyranosoate
  参考文献：
  名称：

  Synthesis and anti-influenza virus activity of 4-guanidino-7-substituted Neu5Ac2en derivatives

  摘要：

  Substitution of 7-OH by small hydrophobic groups on zanamivir resulted in the retaining of low nanomolar inhibitory activities against not only influenza A virus sialidase but also influenza A virus in cell culture. These compounds were prepared by treatment of the corresponding 7-substituted sialic acids derived from 4-modified N-acetyl-D-mannosamine (ManNAc) using enzyme-catalyzed aldol condensation. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00328-1
• 作为产物：
  描述：

  2-acetamido-2,4-dideoxy-4-fluoro-α,β-D-glucopyranose 在 N-acetylglucosamine 2-epimerase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 6.0h， 生成 2-acetamido-2,4-dideoxy-4-fluoro-D-mannopyranoside
  参考文献：
  名称：

  使用全细胞催化剂合成唾液酸，其衍生物和类似物

  摘要：

  唾液酸（Sias）是细胞表面聚糖的重要成分。大量使用Sias可以方便地开发基于碳水化合物的疫苗和小分子药物。现在，我们提出了一种通过使用全细胞催化剂来合成Sias的各种天然形式和非天然衍生物或类似物的简便方法，该方法是通过将包含必需酶基因的质粒添加到大肠杆菌的代谢工程菌株中来构建的。掺入的酶（N-乙酰氨基葡萄糖2-表异构酶和N-乙酰神经氨酸醛缩酶）使细胞催化剂可以通过易于扩展的发酵过程将各种简单廉价的糖类转化为各种与Sia相关的化合物。此外，使用这种全细胞生物转化结合三个常规酶促反应的合成提供了一系列复杂的含Sia的聚糖（唾液寡糖）及其带有不同取代基的衍生物。本文所述的方法应允许大规模且经济地生产Sias和唾液酸低聚糖，并且可以补充现有的化学和酶促策略。

  DOI：

  10.1002/chem.201703083

文献信息

• Chemoenzymatic synthesis of sialosides containing C7-modified sialic acids and their application in sialidase substrate specificity studies
  作者：Zahra Khedri、Yanhong Li、Saddam Muthana、Musleh M. Muthana、Ching-Wen Hsiao、Hai Yu、Xi Chen

  DOI：10.1016/j.carres.2014.02.021

  日期：2014.5

  chemoenzymatic synthesis of α2-3- and α2-6-linked sialyl para-nitrophenyl galactosides in which the C7-hydroxyl group in sialic acid (N-acetylneuraminic acid, Neu5Ac, or 2-keto-3-deoxynonulosonic acid, Kdn) was systematically substituted by -F, -OMe, -H, and -N3 groups. Substrate specificity study of bacterial and human sialidases using the obtained sialoside library containing C7-modified sialic acids showed

  唾液酸苷中唾液酸甘油侧链的修饰通过唾液酸结合蛋白和唾液酸酶来调节其识别。然而，有限的工作集中在具有C7修饰的唾液酸的唾液酸化物的合成和功能研究上。在这里，我们报告化学合成C4修饰的ManNAc和甘露糖及其作为唾液酸前体在高效一锅三酶系统中化学合成α2-3和α2-6连接的唾液酸对硝基苯基半乳糖苷的唾液酸前体的应用。唾液酸中的C7-羟基（N-乙酰神经氨酸，Neu5Ac或2-酮-3-脱氧壬二酸，Kdn）被-F，-OMe，-H和-N3系统取代。使用获得的含有C7修饰的唾液酸的唾液酸文库，对细菌和人唾液酸酶的底物特异性研究表明，含有C7-脱氧Neu5Ac的唾液酸苷是所有测试的细菌唾液酸酶（而非人NEU2）的选择性底物。从唾液酸酶底物特异性获得的信息可用于指导对细菌唾液酸酶具有选择性的新抑制剂的设计。
• Process for producing sugar peptide having asparagine sugar chain and the sugar peptide
  申请人：Kajihara Yasuhiro

  公开号：US20050222382A1

  公开（公告）日：2005-10-06

  Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of an amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.

  具有至少一个天冬氨酸连接的寡糖在肽链的所需位置的糖肽的制备方法为：(1)酯化树脂的羟基和氨基保护有脂溶性保护基的氨基酸的羧基，(2)去除保护基以形成自由氨基，(3)酰胺化自由氨基和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(4)去除保护基，(5)重复步骤(3)和(4)，(6)酰胺化天冬氨酸连接的寡糖的天冬氨酸部分和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(7)去除保护基，(8)酰胺化自由氨基和氨基酸的羧基，该氨基酸保护有脂溶性保护基，(9)重复步骤(7)和(8)，(10)去除保护基，(11)用酸切断树脂;将唾液酸或其衍生物转移至上述糖肽获得的糖肽。
• Process for preparing glycopeptides having asparagine-linked oligosaccharides, and the glycopeptides
  申请人：Kajihara Yasuhiro

  公开号：US20090234095A1

  公开（公告）日：2009-09-17

  Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of ah amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.

  获得至少在肽链的所需位置具有至少一个天冬氨酸连接寡糖的肽糖化物的方法如下： （1）酯化树脂的羟基和带有脂溶性保护基（AGFPG）的氨基酸的羧基； （2）去除保护基以形成自由氨基； （3）酰胺化自由氨基和带有AGFPG的氨基酸的羧基； （4）去除保护基； （5）重复步骤（3）和（4）； （6）酰胺化天冬氨酸连接寡糖的天冬氨酸部分的自由氨基和羧基； （7）去除保护基； （8）酰胺化带有AGFPG的氨基酸的自由氨基和羧基； （9）重复步骤（7）和（8）； （10）去除保护基； （11）用酸切断树脂； 将唾液酸或其衍生物转移至上述肽糖化物获得的肽糖化物。
• PROCESS FOR PREPARING GLYCOPEPTIDES HAVING ASPARAGINE-LINKED OLIGOSACCHARIDES, AND THE GLYCOPEPTIDES
  申请人：Kajihara Yasuhiro

  公开号：US20120035345A1

  公开（公告）日：2012-02-09

  Glycopeptide having at least one asparagine-linked oligosaccharide at a desired position of the peptide chain obtained by: (1) esterifying hydroxyl of a resin and carboxyl of an amino acid having amino group nitrogen protected with a fat-soluble protective group (AGFPG), (2) removing the protective group to form a free amino group, (3) amidating the free amino group and carboxyl of an amino acid having AGFPG, (4) removing the protective group, (5) repeating the steps (3) and (4), (6) amidating the free amino group and carboxyl of the asparagine portion of an asparagine-linked oligosaccharide having AGFPG, (7) removing the protective group, (8) amidating the free amino group and carboxyl of an amino acid having AGFPG, (9) repeating steps (7) and (8), (10) removing the protective group, and (11) cutting off the resin with an acid; glycopeptide obtained by transferring sialic acid or a derivative thereof to the above glycopeptide.

  具有至少一个天冬氨酸连接寡糖在肽链的所需位置的糖肽，其制备方法为：（1）酯化树脂的羟基和具有脂溶性保护基（AGFPG）的氨基酸的羧基，其氨基团氮原子受保护；（2）去除保护基以形成自由氨基团；（3）酰胺化自由氨基团和具有AGFPG的氨基酸的羧基；（4）去除保护基；（5）重复步骤（3）和（4）；（6）酰胺化具有AGFPG的天冬氨酸连接寡糖的天冬氨酸部分的自由氨基团和羧基；（7）去除保护基；（8）酰胺化自由氨基团和具有AGFPG的氨基酸的羧基；（9）重复步骤（7）和（8）；（10）去除保护基；（11）用酸切割树脂；将唾液酸或其衍生物转移给上述糖肽获得的糖肽。
• Synthesis of Sialic Acids, Their Derivatives, and Analogs by Using a Whole-Cell Catalyst
  作者：Xun Lv、Hongzhi Cao、Baixue Lin、Wei Wang、Wande Zhang、Qian Duan、Yong Tao、Xue-Wei Liu、Xuebing Li

  DOI：10.1002/chem.201703083

  日期：2017.10.26

  Sialic acids (Sias) are important constituents of cell surface glycans. Ready access to Sias in large quantities would facilitate the development of carbohydrate‐based vaccines and small‐molecule drugs. We now present a facile method for synthesizing various natural forms and non‐natural derivatives or analogs of Sias by using a whole‐cell catalyst, which is constructed by adding a plasmid containing

  唾液酸（Sias）是细胞表面聚糖的重要成分。大量使用Sias可以方便地开发基于碳水化合物的疫苗和小分子药物。现在，我们提出了一种通过使用全细胞催化剂来合成Sias的各种天然形式和非天然衍生物或类似物的简便方法，该方法是通过将包含必需酶基因的质粒添加到大肠杆菌的代谢工程菌株中来构建的。掺入的酶（N-乙酰氨基葡萄糖2-表异构酶和N-乙酰神经氨酸醛缩酶）使细胞催化剂可以通过易于扩展的发酵过程将各种简单廉价的糖类转化为各种与Sia相关的化合物。此外，使用这种全细胞生物转化结合三个常规酶促反应的合成提供了一系列复杂的含Sia的聚糖（唾液寡糖）及其带有不同取代基的衍生物。本文所述的方法应允许大规模且经济地生产Sias和唾液酸低聚糖，并且可以补充现有的化学和酶促策略。