N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide | 1040191-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide
• 英文别名: N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[2-(4-methylphenyl)sulfonylhydrazinyl]oxan-3-yl]acetamide
• CAS: 1040191-33-0
• 化学式: C₁₅H₂₃N₃O₇S
• 分子量: 389.43
• InChiKey: BGGMJCNEOYESHL-KJWHEZOQSA-N

物化性质

• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 在 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 Bifidobacterium infantis D-galactosyl-β1-3-N-acetyl-D-hexosamine phosphorylase 、 Streptococcus pneumoniae galactokinase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.17h， 生成 Galβ1-3GlcNAcβProN3
  参考文献：
  名称：

  克级的Lewis a（Lea）抗原和包含多种唾液酸形式的唾液酸化的Lewis a（sLea）抗原的简便化学酶法合成

  摘要：

  已经开发了一种有效的简化的化学酶方法，用于革兰氏合成Lewis a血管生成素（LeaβProN3）和唾液酸Lewis a抗原（sLeaβProN3）库，其中包含不同的唾液酸形式。最初，将一步一步将市售的廉价N-乙酰氨基葡糖（GlcNAc）转化为其N'-糖基对甲苯磺酰肼。随后进行化学糖基化，使用该无保护基的方法以高收率（82％）合成了GlcNAcβProN3。GlcNAcβProN3的顺序一锅多酶（OPME）β1-3-半乳糖基化，然后进行OPMEα1-4-岩藻糖基化反应，以克为单位生成了目标LeaβProN3。

  DOI：

  10.1016/j.carres.2018.12.004
• 作为产物：
  描述：

  N-乙酰氨基葡萄糖 、 对甲苯磺酰肼 在 deuterated sodium acetate 作用下， 以 氘代二甲亚砜 、 water-d2 为溶剂， 反应 72.0h， 生成 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide
  参考文献：
  名称：

  Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution

  摘要：

  Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong alpha-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acetylglucosamine, and either p-toluenesulfonyl hydrazide or an N-methylhydroxylamine, was carried out to gain insight into the optimal conditions for the formation of these useful conjugates, and their stability. Their apparent association constants (974 M-1) at pH 4.5; as well, as rate constants for hydrolysis, at pH 4.0, 5.0 and 6.0 (37 degrees C), were determined. The half-lives of the conjugates varied between 3 h and 300 days, All the compounds were increasingly stable as the pH approached neutrality. Conjugate hydrolysis rates mirrored those found for O-glycoside hydrolysis where conjugates formed from electron-rich monosaccharides hydrolyzed more rapidly. (C) 2008 Elsevier Ltd. All rights reserved

  DOI：

  10.1016/j.carres.2008.11.007

文献信息

• Generation of a glycosylated asparagine residue through chemoselective acylation of a glycosylhydrazide
  作者：Katie A. Rykaczewski、Kate E. Sabourin、Paul J. Goo、Lydia H. Griggs、Saumya Jain、Paxton A.M. Reed、Joseph M. Langenhan

  DOI：10.1016/j.carres.2020.108022

  日期：2020.7

  anomeric N-acylation of a glycosylhydrazide. We show that this transformation can be harnessed to generate amino acid building blocks including FmocAsn(GlcNAc)OH (1), a residue that has been previously shown to be a competent reagent in the solid-phase peptide synthesis of N-linked glycopeptides.

  在此，我们报告了糖基酰肼的第一个选择性异头 N-酰化。我们表明，可以利用这种转化来生成氨基酸构建块，包括 FmocAsn(GlcNAc)OH (1)，该残基之前已被证明是 N 连接糖肽固相肽合成中的有效试剂。
• Protecting Group Free Glycosidations Using <i>p</i>-Toluenesulfonohydrazide Donors
  作者：Anna V. Gudmundsdottir、Mark Nitz

  DOI：10.1021/ol801232f

  日期：2008.8.21

  N'-Glycopyranosylsulfonohydrazides are introduced as glycosyl donors for protecting group free synthesis of O-glycosides, glycosyl azides, and oxazolines. Mono- and disaccharides containing a reducing terminal N-acetylglucosamine residue were condensed with p-toluenesulfonylhydrazide to give the desired beta- d-pyranose donors. These donors can be activated with NBS and then glycosidated with the desired

  引入N'-甘露糖基磺酰肼作为糖基供体，用于保护O-糖苷，糖基叠氮化物和恶唑啉的无基团合成。将含有还原性末端N-乙酰氨基葡糖残基的单糖和二糖与对甲苯磺酰肼缩合，得到所需的β-d-吡喃糖供体。这些供体可以用NBS活化，然后用所需的醇糖基化或转化为恶唑啉或糖基叠氮化物。
• Protecting-Group-Free Synthesis of Glycosyl 1–Phosphates
  作者：Landon John G. Edgar、Somnath Dasgupta、Mark Nitz

  DOI：10.1021/ol3019083

  日期：2012.8.17

  Glycosyl 1-phosphates enriched in the alpha-anomer are obtained without the use of protecting groups in two steps starting from the free hemiacetal. Condensation of free hemiacetals with toluenesulfonylhydrazide yields a range of glycosylsulfonohydrazide donors which can be oxidized using cupric chloride in the presence of phosphoric acid and the coordinating additive 2-methyl-2-oxazoline to give useful yields of the fully deprotected glycosyl 1-phosphates.
• Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution
  作者：Anna V. Gudmundsdottir、Caroline E. Paul、Mark Nitz

  DOI：10.1016/j.carres.2008.11.007

  日期：2009.2

  Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong alpha-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acetylglucosamine, and either p-toluenesulfonyl hydrazide or an N-methylhydroxylamine, was carried out to gain insight into the optimal conditions for the formation of these useful conjugates, and their stability. Their apparent association constants (974 M-1) at pH 4.5; as well, as rate constants for hydrolysis, at pH 4.0, 5.0 and 6.0 (37 degrees C), were determined. The half-lives of the conjugates varied between 3 h and 300 days, All the compounds were increasingly stable as the pH approached neutrality. Conjugate hydrolysis rates mirrored those found for O-glycoside hydrolysis where conjugates formed from electron-rich monosaccharides hydrolyzed more rapidly. (C) 2008 Elsevier Ltd. All rights reserved
• Facile chemoenzymatic synthesis of Lewis a (Lea) antigen in gram-scale and sialyl Lewis a (sLea) antigens containing diverse sialic acid forms
  作者：Nova Tasnima、Hai Yu、Xuebin Yan、Wanqing Li、An Xiao、Xi Chen

  DOI：10.1016/j.carres.2018.12.004

  日期：2019.1

  LeaβProN3 in gram-scale. Structurally diverse sialic acid forms was successfully introduced using a OPME sialylation reation containing a CMP-sialic acid synthetase and Pasteurella multocida α2-3-sialyltransferase 1 (PmST1) mutant PmST1 M144D with or without a sialic acid aldolase to form sLeaβProN3 containing naturally occurring or non-natural sialic acid forms in preparative scales.

  已经开发了一种有效的简化的化学酶方法，用于革兰氏合成Lewis a血管生成素（LeaβProN3）和唾液酸Lewis a抗原（sLeaβProN3）库，其中包含不同的唾液酸形式。最初，将一步一步将市售的廉价N-乙酰氨基葡糖（GlcNAc）转化为其N'-糖基对甲苯磺酰肼。随后进行化学糖基化，使用该无保护基的方法以高收率（82％）合成了GlcNAcβProN3。GlcNAcβProN3的顺序一锅多酶（OPME）β1-3-半乳糖基化，然后进行OPMEα1-4-岩藻糖基化反应，以克为单位生成了目标LeaβProN3。