D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-β-D-galactopyranose | 93601-70-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-β-D-galactopyranose
• 英文别名: 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-β-D-galactopyranose；β-D-Galp-(1->3)-β-D-GalpNAc；T antigen；beta-D-Galp-(1->3)-beta-D-GalpNAc；N-[(2R,3R,4R,5R,6R)-2,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 93601-70-8
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: HMQPEDMEOBLSQB-UFLFEMAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-β-D-galactopyranose 在 sodium tetrahydroborate 、 potassium hydroxide 作用下， 反应 2.0h， 生成 2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-D-galactitol
  参考文献：
  名称：

  Enhanced Detection of Sialylated and Sulfated Glycans with Negative Ion Mode Nanoliquid Chromatography/Mass Spectrometry at High pH

  摘要：

  研究了 pH 11 下多孔石墨碳柱上的负离子模式纳液相色谱/质谱 (nano-LC/MS) 分析方法，并与 pH 8 下的毛细管 LC/MS 进行比较，以分析中性和酸性聚糖糖醇。使用含有 0.04% 氢氧化铵的乙腈梯度对低聚糖进行色谱分析，并使用配备改进的纳喷雾接口的线性离子阱质谱仪 (LTQ) 进行分析。对酸性 N- 和 O- 聚糖标准品的分析表明，上样 1−3 fmol 时可以获得高质量的 MS/MS 谱图，与 pH 8 下的毛细管 LC/MS 相比，灵敏度提高了 10 倍。使用纳米 LC/MS 和高 pH 下的 MS/MS 对猪结肠粘蛋白的 O-聚糖混合物进行分析，结果显示，在一项分析中发现了 170 种寡糖，主要对应于最多有 11 个残基的硫酸化聚糖。使用毛细管 LC/MS 对同一样品进行分析表明，多重硫酸化聚糖的灵敏度较低。对来自人类结肠活检的 MUC2 上的 O-连接寡糖进行的 Nano-LC/MS 分析也表明，与仅具有一个唾液酸残基的寡糖相比，具有多个唾液酸基团的寡糖的电离增加。因此，高 pH 条件下的 Nano-LC/MS 是分析酸性寡糖的一种高度灵敏的方法。

  DOI：

  10.1021/ac902602e
• 作为产物：
  描述：

  在 palladium on activated charcoal ammonium hydroxide 、 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 D-galactopyranosyl-β-(1,3)-2-acetamido-2-deoxy-β-D-galactopyranose
  参考文献：
  名称：

  A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units

  摘要：

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.

  DOI：

  10.1021/jo00068a030

文献信息

• Enzymatic and Chemoenzymatic Syntheses of Disialyl Glycans and Their Necrotizing Enterocolitis Preventing Effects
  作者：Hai Yu、Xuebin Yan、Chloe A Autran、Yanhong Li、Sabrina Etzold、Joanna Latasiewicz、Bianca M. Robertson、Jiaming Li、Lars Bode、Xi Chen

  DOI：10.1021/acs.joc.7b02167

  日期：2017.12.15

  novel disialyl glycans have been designed and synthesized by enzymatic or chemoenzymatic methods. Noticeably, two disialyl tetraoses have been produced by enzymatic sialylation of chemically synthesized thioethyl β-disaccharides followed by removal of the thioethyl aglycon. Dose-dependent and single-dose comparison studies showed varying NEC-preventing effects of the disialyl glycans in neonatal rats

  坏死性小肠结肠炎（NEC）是早产儿中最常见和最具破坏性的肠道疾病之一。满足这种特殊和高度脆弱人群临床需求的疗法极为有限。特定的人乳低聚糖（HMO），二唾液酸内酯-N-四糖（DSLNT）被证明有助于母乳喂养，因为它可以预防新生大鼠模型中的NEC，并且在一项人类临床研究中与较低的NEC风险相关。本文中，描述了先前显示出具有NEC预防作用的两个DSLNT类似物的克级合成。另外，已经通过酶促或化学酶促方法设计和合成了四种新颖的二唾液酸聚糖。明显地，通过化学合成的硫乙基β-二糖的酶促唾液酸化，然后除去硫乙基糖苷配基，已经产生了两种二唾液酸四糖。剂量依赖性和单剂量比较研究表明，新生大鼠中二唾液酸聚糖的NEC预防作用各不相同。
• A combined chemical and enzymatic strategy for the construction of carbohydrate-containing antigen core units
  作者：Gary C. Look、Yoshitaka Ichikawa、Gwo Jenn Shen、Pi Wan Cheng、Chi Huey Wong

  DOI：10.1021/jo00068a030

  日期：1993.7

  Glycosidase-mediated coupling of glycal acceptors with galactose donors affords beta1,3-linked disaccharides that are versatile intermediates for further chemical and enzymatic manipulation. The utility of these disaccharides is demonstrated by the elaboration of these compounds into the type I and type IV core disaccharides of carbohydrate-containing antigens. Further conversion of the type IV disaccharide to a mucin-type trisaccharide (Galbeta1,3(GlcNAcbeta1,6)GalNAc) was accomplished with the use of a beta1,6-N-acetylglucosaminyltransferase. This combined use of enzymatic and chemical methodologies allows for the rapid assembly, with high regio- and stereoselectivity, of core oligosaccharides of biologically important glycoconjugates.
• Enhanced Detection of Sialylated and Sulfated Glycans with Negative Ion Mode Nanoliquid Chromatography/Mass Spectrometry at High pH
  作者：Kristina A. Thomsson、Malin Bäckström、Jessica M. Holmén Larsson、Gunnar C. Hansson、Hasse Karlsson

  DOI：10.1021/ac902602e

  日期：2010.2.15

  Negative ion mode nanoliquid chromatography/mass spectrometry (nano-LC/MS) on porous graphitic carbon columns at pH 11 was studied and compared to capillary LC/MS at pH 8 for the analysis of neutral and acidic glycan alditols. Oligosaccharides were chromatographed with an acetonitrile gradient containing 0.04% ammonium hydroxide and analyzed with a linear ion trap mass spectrometer (LTQ) equipped with a modified nanospray interface. Analysis of acidic N- and O-glycan standards revealed that good quality MS/MS spectra could be obtained when loading 1−3 fmol, a 10-fold increase in sensitivity compared to capillary-LC/MS at pH 8. Analysis of a complex mixture of O-glycans from porcine colonic mucins with nano-LC/MS and MS/MS at high pH revealed 170 oligosaccharides in one analysis, predominantly corresponding to sulfated glycans with up to 11 residues. Analysis of the same sample with capillary-LC/MS showed a lower sensitivity for multiply sulfated glycans. Nano-LC/MS of O-linked oligosaccharides on MUC2 from a human colon biopsy also illustrated that the ionization of oligosaccharides with multiple sialic acid groups was increased compared to those with only one sialic acid residue. Nano-LC/MS at high pH is, thus, a highly sensitive approach for the analysis of acidic oligosaccharides.

  研究了 pH 11 下多孔石墨碳柱上的负离子模式纳液相色谱/质谱 (nano-LC/MS) 分析方法，并与 pH 8 下的毛细管 LC/MS 进行比较，以分析中性和酸性聚糖糖醇。使用含有 0.04% 氢氧化铵的乙腈梯度对低聚糖进行色谱分析，并使用配备改进的纳喷雾接口的线性离子阱质谱仪 (LTQ) 进行分析。对酸性 N- 和 O- 聚糖标准品的分析表明，上样 1−3 fmol 时可以获得高质量的 MS/MS 谱图，与 pH 8 下的毛细管 LC/MS 相比，灵敏度提高了 10 倍。使用纳米 LC/MS 和高 pH 下的 MS/MS 对猪结肠粘蛋白的 O-聚糖混合物进行分析，结果显示，在一项分析中发现了 170 种寡糖，主要对应于最多有 11 个残基的硫酸化聚糖。使用毛细管 LC/MS 对同一样品进行分析表明，多重硫酸化聚糖的灵敏度较低。对来自人类结肠活检的 MUC2 上的 O-连接寡糖进行的 Nano-LC/MS 分析也表明，与仅具有一个唾液酸残基的寡糖相比，具有多个唾液酸基团的寡糖的电离增加。因此，高 pH 条件下的 Nano-LC/MS 是分析酸性寡糖的一种高度灵敏的方法。