β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside | 50611-42-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside
• 英文别名: 1-thio-β-D-lactose；β-D-1-thiolactose；β-D-Lac-SH；LacSH；beta-Lactosyl thiol；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-sulfanyloxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 50611-42-2
• 化学式: C₁₂H₂₂O₁₀S
• 分子量: 358.367
• InChiKey: QGXQUPXAQKVWCR-XLOQQCSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  170
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 在 碘 作用下， 以 乙醇 为溶剂， 以76%的产率得到bis[β-D-galactopyranosyl-(1-4)-1-thio-β-D-glucopyranosyl]1,1'-disulfide
  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：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose 在 甲醇 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  烯烃蛋白的硫基糖基化：S-连接的糖缀合物合成

  摘要：

  标记为硫醇化：一种新的糖缀合策略利用非天然含烯烃的氨基酸（高烯丙基甘氨酸，Hag）作为修饰的“标签”和仅对 Hag 烯烃“标签”有选择性的光引发氢糖硫醇化反应。将此方法应用于许多模型蛋白，可以实现完整和精确的位点选择性糖基化生成糖缀合物，例如，在预选位置显示多达 180 个聚糖的病毒样颗粒（参见方案）。

  DOI：

  10.1002/anie.200903135

文献信息

• Characterization of multivalent lactose quantum dots and its application in carbohydrate–protein interactions study and cell imaging
  作者：Yang Yang、Min Yu、Ting-Ting Yan、Zhi-Hui Zhao、Yin-Lin Sha、Zhong-Jun Li

  DOI：10.1016/j.bmc.2010.05.046

  日期：2010.7

  We have previously reported a facile and convenient method for the preparation of a new type of lactose-CdSeS/ZnS quantum dots conjugates (Lac-QDs) that exhibit biocompatibility, noncytotoxicity and specificity to leukocytes. In order to further study the carbohydrate–protein interactions, a series of Lac-QDs with different lactose densities and a PEGylated (n = 3) lactose-QDs conjugate (LacPEG-QDs)

  我们以前已经报道了一种简便而便捷的方法，用于制备新型的乳糖-CdSeS / ZnS量子点缀合物（Lac-QDs），该缀合物表现出对白细胞的生物相容性，非细胞毒性和特异性。为了进一步研究碳水化合物与蛋白质的相互作用，一系列具有不同乳糖密度和聚乙二醇化（n ＝ 3）制备具有更灵活的糖配体的乳糖-QDs缀合物（LacPEG-QDs）。可以通过NMR确定QD上的糖分子的量，这与TGA测定的结果一致。用ICP-OES测定缀合物的分子式。使用SPR测量了结合的QD与PNA蛋白之间的相互作用，结果表明，较高的乳糖密度有利于在相同浓度下的结合亲和力，而Lac-QD的亲和力高于LacPEG-QD。我们进一步使用固相分析来评估Lac-QD和LacPEG-QD在细胞水平上的抗粘附活性。结果表明，与LacPEG-QD相比，Lac-QD具有更强的防止THP1粘附于HUVEC的活性，这与SPR结果一致。我们认为，适当
• Photoinduced Addition of Glycosyl Thiols to Alkynyl Peptides: Use of Free-Radical Thiol−Yne Coupling for Post-Translational Double-Glycosylation of Peptides
  作者：Mauro Lo Conte、Salvatore Pacifico、Angela Chambery、Alberto Marra、Alessandro Dondoni

  DOI：10.1021/jo1008178

  日期：2010.7.2

  peptides has been carried out by a one-pot two-step sequence comprising selective S-propargylation followed by photoinduced (λ max 365 nm) free-radical hydrothiolation with glycosyl thiols. Conditions were established for the sequential introduction of two different thiol residues such as a glycosyl and a biotinyl derivative.

  含半胱氨酸的肽的双糖基化已经通过一锅两步的顺序进行，该步骤包括选择性的S-炔丙基化，然后用糖基硫醇进行光诱导的（λmax 365 nm）自由基氢硫醇化。为依次引入两个不同的硫醇残基（例如糖基和生物素基衍生物）建立了条件。
• <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。
• A Sweet H₂S/H₂O₂ Dual Release System and Specific Protein S-Persulfidation Mediated by Thioglucose/Glucose Oxidase
  作者：Xiang Ni、Xiaolu Li、Tun-Li Shen、Wei-Jun Qian、Ming Xian

  DOI：10.1021/jacs.1c06372

  日期：2021.8.25
• Study of carbohydrate–protein interactions using glyco-QDs with different fluorescence emission wavelengths
  作者：Yang Yang、Xi-Kai Cui、Ming Zhong、Zhong-Jun Li

  DOI：10.1016/j.carres.2012.08.018

  日期：2012.11

  QDs with different fluorescence emission wavelengths were coated with galactose, glucose, and lactose respectively. The formulas of glyco-QDs were determined by NMR and ICP-OES, and the interactions between glyco-QDs and PNA lectin were investigated by SPR. The results showed that multivalent presentation achieved by using QDs as the scaffold is an effective way to enhance the carbohydrate-protein interactions. The K-D for the interaction of PNA with multivalent glyco-QDs is over 3 x 10(6)-fold lower than those with the same free sugars. The specific recognition for the sugar coated on the QDs by lectin is maintained. These sugar-coated QDs could be used as a fluorescent probe to label and identify glycoproteins. Crown Copyright (c) 2012 Published by Elsevier Ltd. All rights reserved.