hydrosulfuryl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside | 679828-92-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hydrosulfuryl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
• 英文别名: GlcNAc(b1-3)Gal(b1-4)b-Glc1SH；N-[(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-sulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 679828-92-3
• 化学式: C₂₀H₃₅NO₁₅S
• 分子量: 561.562
• InChiKey: CLPKXWXUTIXQIT-RDJKAQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.4
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  258
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  hydrosulfuryl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside 在 sodium hydroxide 、 hexa-bromo-polyethylene glycol 6000 、 mercury(II) trifluoroacetate 、 溶剂黄146 作用下， 反应 50.0h， 以54%的产率得到GlcNAcβ(1-3)Galβ(1-4)Glc
  参考文献：
  名称：

  Enzymatic supported synthesis of lacto-N-neotetraose using dendrimeric polyethylene glycol

  摘要：

  The lacto-N-neotetraose tetrasaccharide was synthesized on a new dendrimeric support, based on polyethylene glycol. Starting from 1-thio-beta-D-lactose, the trisaccharide (2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 3)-O-beta-D-galactopyranosyl-(1 --> 4)-1-thio-beta-D-glucopyranose was obtained using Neisseria meningitidis beta-(1--> 3)-N-acetylglucosaminyltransferase according to a soluble synthesis approach, bound on the support and galactosylated using the milk beta-(1 --> 4)-galactosyl transferase to give after cleavage the tetrasaccharide lacto-N-neotetraose. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.11.017
• 作为产物：
  描述：

  β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 在 sodium tetrahydroborate 、 β-(1->3)-N-acetylglycosaminyltransferase 、 cacodylate buffer 、 碘 、 manganese(ll) chloride 作用下， 以 乙醇 为溶剂， 反应 72.0h， 生成 hydrosulfuryl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside
  参考文献：
  名称：

  Enzymatic supported synthesis of lacto-N-neotetraose using dendrimeric polyethylene glycol

  摘要：

  The lacto-N-neotetraose tetrasaccharide was synthesized on a new dendrimeric support, based on polyethylene glycol. Starting from 1-thio-beta-D-lactose, the trisaccharide (2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1 --> 3)-O-beta-D-galactopyranosyl-(1 --> 4)-1-thio-beta-D-glucopyranose was obtained using Neisseria meningitidis beta-(1--> 3)-N-acetylglucosaminyltransferase according to a soluble synthesis approach, bound on the support and galactosylated using the milk beta-(1 --> 4)-galactosyl transferase to give after cleavage the tetrasaccharide lacto-N-neotetraose. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2003.11.017

文献信息

• <scp>Capture‐Release</scp> Strategy Facilitates Rapid Enzymatic Assembly of Oligosaccharides
  作者：Wenyuan Fang、Kan Zhong、Jiansong Cheng、Xian‐Wei Liu、Chang‐Cheng Liu、Zhongfu Wang、Hongzhi Cao

  DOI：10.1002/cjoc.202100744

  日期：2022.2

  A convenient and highly efficient strategy was developed for the simplification of enzymatic synthesis and purification of oligosaccharides. Glycosyl acceptors terminated with a thiol tag were extended by enzymatic modular assembly (EMA) in the aqueous phase, and the desired products were captured during solid-phase workup (SPW) using commercially available thiopropyl Sepharose 6B resin through a reversible

  为简化酶促合成和寡糖的纯化，开发了一种方便且高效的策略。以硫醇标签终止的糖基受体通过水相中的酶模块组装 (EMA) 进行扩展，并在固相处理 (SPW) 期间使用市售的硫丙基琼脂糖凝胶 6B 树脂通过可逆二硫键捕获所需的产物。最后，在二硫苏糖醇（DTT）作为还原剂的存在下，产物从固相树脂中释放出来，树脂可以回收再利用。该策略克服了酶促糖基化中常用的聚合物或离子载体的不确定影响，并显示出与所有 10 种酶模块的完美兼容性，用于快速组装一系列复杂的寡糖。