4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid) | 28079-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid)
• 英文别名: 2-O-(p-nitrophenyl) N-acetyl-α-neuraminoside；4-nitrophenyl β-D-sialoside；4-nitrophenyl β-D-N-acetylneuraminic acid；NeuAc(b)-O-Ph(4-NO2)；(2R,4S,5R,6R)-5-acetamido-4-hydroxy-2-(4-nitrophenoxy)-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 28079-86-9
• 化学式: C₁₇H₂₂N₂O₁₁
• 分子量: 430.368
• InChiKey: OICUZSPXIJAAEA-CXECBNLGSA-N

物化性质

• 沸点：
  853.3±65.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  212
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid) 、 在 Trypanosoma cruzi transsialidase 、 sodium hydroxide 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  [EN] SYNTHESIS OF SIALYLATED/FUCOSYLATED OLIGOSACCHARIDES
  [FR] SYNTHÈSE D'OLIGOSACCHARIDES SIALYLÉS/FUCOSYLÉS

  摘要：

  本发明涉及一种化学酶合成公式1的寡糖的方法，其中R从-OH，-N3和-OR6中选择，其中R6从烯丙基选项中选择，烯丙基可以被一个或多个甲基取代，丙炔基可以被一个或多个甲基取代，2-三甲基硅乙基，-(CH2)n -NH2和-(CH2)n -N3，其中整数n为10，优选为2或3，R1从唾液酸基团，-SO3H和-CH(R5)-COOH中选择，其中R5从H，烷基和苄基中选择，R2从H和岩藻糖基中选择，R3从H和唾液酸基中选择，R4从H和岩藻糖基中选择，前提是R3和R4中仅有一个是H，A从一个化学键和双价碳水化合物连接物中选择，具有重要的生物活性和在制药和食品工业中有重要的商业价值。

  公开号：

  WO2014167537A1
• 作为产物：
  描述：

  对硝基苯酚 在 lithium hydroxide 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 生成 4-nitrophenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid)
  参考文献：
  名称：

  Unexpected Stability of Aryl β-N-Acetylneuraminides in Neutral Solution:  Biological Implications for Sialyl Transfer Reactions

  摘要：

  A reagent panel comprised of seven aryl beta-D-N-acetylneuraminides was synthesized and then used to probe the mechanisms of nonenzymatic hydrolysis. These reactions proceeded via four independent pathways: (1) acid-catalyzed hydrolysis of the neutral molecule; (2) acid-catalyzed hydrolysis of the anionic form, or its kinetic equivalent spontaneous hydrolysis of the neutral form; (3) spontaneous hydrolysis of the anionic form; and (4) a base-promoted pathway. The pH-independent spontaneous hydrolysis of 4-nitrophenyl alpha-D-N-acetylneuraminide (5) occurs at a rate that is over 100 times faster than that of the corresponding reaction of 4-nitrophenyl O-D-N-acetylneuraminide (4a). Spontaneous hydrolyses of four aryl beta-D-N-acetylneuraminides displayed a beta(lg) value of -1.24 +/- 0.16 (pH = 8.1, T= 100 degrees C), and at a pH value of 1.0 (50 degrees C), all seven panel members gave a beta(lg) value of 0.14 +/- 0.08. The aqueous ethanolyses of 4a and 5 gave similar products and displayed sensitivity parameters (m) in a standard Winstein-Grunwald analysis of -0.04 +/- 0.01 and +0.23 +/- 0.02, respectively. These results, plus the activation parameters calculated for the spontaneous hydrolyses of the anionic forms of 5 (Delta H = 116 +/- 2 U mol(-1) and Delta S = 27 +/- 4 J mol(-1) K-1) and 4a (Delta H = 138 3 U mol(-1) and AS = 59 +/- 8 J mol(-1) K-1), are inconsistent with anomeric carboxylate assistance occurring during the hydrolysis reactions, and the likely cause for the enhanced reactivity of 5 in comparison to that of 4a is an increase in ground-state steric strain.

  DOI：

  10.1021/ja042280e

文献信息

• Process for producing novel sialo-sugar chain
  申请人：WAKAYAMA UNIVERSITY

  公开号：US10975346B2

  公开（公告）日：2021-04-13

  The present invention provides a novel sialo-sugar chain, a process for producing the sialo-sugar chain, and a device for producing the sialo-sugar chain. A sialo-sugar chain can be easily and efficiently mass-produced by reacting a sugar wherein a hydroxy groups is substituted with an alkynyl group (herein sometimes referred to as “alkynylated sugar”) with a specific sialic acid donor in the presence of a sialic acid-introducing enzyme.

  本发明提供了一种新型硅糖链、一种生产硅糖链的工艺和一种生产硅糖链的装置。通过使羟基被炔基取代的糖（此处有时称为 "炔化糖"）与特定的硅酸供体在硅酸导入酶的存在下发生反应，可以方便、高效地大量生产硅酸糖链。
• NEURAMINIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR MEDICAL USE
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020137791A1

  公开（公告）日：2002-09-26

  Compounds of formula (I) or their salts or esters: 1 [wherein R 1 is alkyl or haloalkyl; R 2 and R 3 each represents hydrogen or aliphatic acyl; X is hydroxy, halogen, alkoxy, or a group of formula R a O—, where R a is aliphatic acyl; Y is a group of formula R b R c N— or R b R c N—O—, where R b and R c each is hydrogen or alkyl; and Z is oxygen or sulfur] have excellent sialidase inhibitory activity and are therefore useful for the treatment and prevention of influenza and other viral diseases where the replication of the virus is susceptible to sialidase inhibitors.

  式(I)化合物或其盐或酯： 1 其中 R 1 是烷基或卤代烷基；R 2 和 R 3 分别代表氢或脂族酰基；X 是羟基、卤素、烷氧基或式 R a O-，其中 R a 是脂肪酰基；Y 是式 R b R c N- 或 R b R c N-O- ，其中 R b 和 R c 均为氢或烷基；Z 为氧或硫&rsqb；具有极佳的硅糖苷酶抑制活性，因此可用于治疗和预防流感及其他病毒复制易受硅糖苷酶抑制剂影响的病毒性疾病。
• PROCESS FOR PRODUCING NOVEL SIALO-SUGAR CHAIN
  申请人：Wakayama University

  公开号：EP2759548B1

  公开（公告）日：2016-09-07
• TRANS-SIALIDASE AND METHODS OF USE AND MAKING THEREOF
  申请人：NEW YORK UNIVERSITY

  公开号：EP0586687A1

  公开（公告）日：1994-03-16
• EP0586687A4
  申请人：——

  公开号：EP0586687A4

  公开（公告）日：1996-04-17