thiophenyl(methyl-5-N-butanoyl-4,7,8,9-tetra-OAc-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylate) | 1000890-38-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: thiophenyl(methyl-5-N-butanoyl-4,7,8,9-tetra-OAc-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylate)
• 英文别名: methyl (thiophenyl 5-N-butanoyl-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate
• CAS: 1000890-38-9
• 化学式: C₂₈H₃₇NO₁₂S
• 分子量: 611.667
• InChiKey: LZRDEOMQHNKDSA-DNJARQNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.08
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  thiophenyl(methyl-5-N-butanoyl-4,7,8,9-tetra-OAc-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylate) 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of N-Acyl Modified Sialic Acids as Inhibitors of Adenoviruses Causing Epidemic Keratoconjunctivitis

  摘要：

  The adenovirus serotype Ad37 binds to and infects human corneal epithelial (HCE) cells through attachment to cellular glycoproteins carrying terminal sialic acids. By use of the crystallographic structure of the sialic acid-interacting domain of the Ad37 fiber protein in complex with sialyllactose, a set of N-acyl modified sialic acids were designed to improve binding affinity through increased hydrophobic interactions. These N-acyl modified sialic acids and their corresponding multivalent human serum albumin (HSA) conjugates were synthesized and tested in Ad37 cell binding and cell infectivity assays. Compounds bearing small substituents were as effective inhibitors as sialic acid. X-ray crystallography and overlays with the Ad37-sialyllactose complex showed that the N-acyl modified sialic acids were positioned in the same orientation as sialic acid. Their multivalent counterparts achieved a strong multivalency effect and were more effective to prevent infection than the monomers. Unfortunately, they were less active as inhibitors than multivalent sialic acid.

  DOI：

  10.1021/jm801609s
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 N,N-二丁基丁烷-1-胺,硫酸 、 甲烷磺酸 、 sodium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成 thiophenyl(methyl-5-N-butanoyl-4,7,8,9-tetra-OAc-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylate)
  参考文献：
  名称：

  CMP-唾液酸衍生物的化学合成和酶促测试

  摘要：

  唾液酸修饰：Cyclo Sal核苷酸用于制备单磷酸连接的糖核苷酸，例如TMP-β-Gal和CMP - N-乙酰基神经氨酸以及四种唾液酸衍生物，它们的氨基官能团具有不同的修饰。在细菌多唾液酸转移酶催化的聚合反应中研究了CMP-唾液酸衍生物。

  DOI：

  10.1002/cbic.201200471

文献信息

• Transsialidase fromTrypanosoma cruzi for Regio- and Stereoselective Synthesis of N-Acyl-Modified Sialylated Oligosaccharides and Measurement of Transfer Rates
  作者：Andreas Schroven、Sebastian Meinke、Patrick Ziegelmüller、Joachim Thiem

  DOI：10.1002/chem.200700439

  日期：2007.11.5

  Recombinant transsialidase from Trypanosoma cruzi (TcTS) was used for the sialylation with natural and non-natural derivatives of neuraminic acid. Neu5Ac-alpha(2-->3)-Gal-beta(1-->6)-Glc-alphaOMe was prepared in 80 % yield. Correspondingly, the modified trisaccharide derivatives Neu5Prop-alpha(2-->3)-Gal-beta(1-->6)-Glc-alphaOMe (32 %) and Neu5Gc-alpha(2-->3)-Gal-beta(1-->6)-Glc-alphaOMe (Prop=propanoyl

  来自克鲁氏锥虫（TcTS）的重组转唾液酸酶用于与神经氨酸的天然和非天然衍生物进行唾液酸化。Neu5Ac-alpha（2-> 3）-Gal-beta（1→6）-Glc-alphaOMe的制备产率为80％。相应地，修饰的三糖衍生物Neu5Prop-alpha（2-> 3）-Gal-beta（1-> 6）-Glc-alphaOMe（32％）和Neu5Gc-alpha（2-> 3）-Gal-beta以60％的收率分别获得（1→6）-Glc-alphaOMe（Prop =丙酰基，Gc =乙二醇基）。