beta-D-半乳糖基-(1→3)-N-乙酰基-D-半乳糖胺 | 3554-90-3

• 物质功能分类: 生物化工 - 糖类化合物 - 寡糖
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: beta-D-半乳糖基-(1→3)-N-乙酰基-D-半乳糖胺
• 中文别名: 3)-N-乙酰基-D-半乳糖胺
• 英文名称: 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-D-galactose
• 英文别名: Thomsen-friedenreich antigen；N-[(2R,3R,4S,5R)-4,5,6-trihydroxy-1-oxo-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-yl]acetamide
• CAS: 3554-90-3
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: QCQYVCMYGCHVMR-AAZUGDAUSA-N

物化性质

• 熔点：
  159-160°C
• 沸点：
  858.1±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇（轻微加热）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  206
• 氢给体数：
  8
• 氢受体数：
  11

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  beta-D-半乳糖基-(1→3)-N-乙酰基-D-半乳糖胺 在 lead(IV) acetate 、 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 25.0h， 生成 3-acetamido-3-deoxy-2-O-(β-D-galactopyranosyl)-L-threose
  参考文献：
  名称：

  Sequential Removal of Monosaccharides from the Reducing End of Oligosaccharides. 2. Fundamental Studies of a Reaction between Hydrazino Compounds and Sugars Having a Glycosyl Moiety on a Carbon Atom Adjacent to a Carbonyl Group

  摘要：

  Hydrazine and certain hydrazino derivatives react with sugars having a glycosidic substituent, where the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto group of the aglycon, resulting in cleavage of the glycosidic linkage. The reaction proceeds whether the glycon is of the alpha or beta configuration. The released glycosyl moiety, in the presence of excess hydrazino compound, reacts further to give a hydrazone derivative. Removal of the hydrazone group gives the reducing sugar derived from the glycon.

  DOI：

  10.1021/jo00130a026
• 作为产物：
  描述：

  口服葡萄糖 在 D-galactosyl-β1–3-N-acetyl-D-hexosamine phosphorylase 、 galactose kinase from Bifidobacterium infantis 作用下， 生成 beta-D-半乳糖基-(1→3)-N-乙酰基-D-半乳糖胺
  参考文献：
  名称：

  Two-Step Chemoenzymatic Detection of N-Acetylneuraminic Acid−α(2-3)-Galactose Glycans

  摘要：

  Sialic acids are typically linked alpha(2-3) or alpha(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-alpha(2-3)-galactose glycans is described.

  DOI：

  10.1021/jacs.6b07132

文献信息

• Regioselectivity in β-Galactosidase-catalyzed Transglycosylation for the Enzymatic Assembly of<scp>D</scp>-Galactosyl-<scp>D</scp>-mannose
  作者：Mariko MIYASATO、Katsumi AJISAKA

  DOI：10.1271/bbb.68.2086

  日期：2004.1

  different origins. The relative hydrolysis rate of Gal beta-pNP and D-galactosyl-D-mannoses, of various linkages, was also measured in the presence of beta-1,3-galactosidase and was found to correlate well with the ratio of disaccharides formed by transglycosylation. The unexpected regioselectivity using D-mannose can therefore be explained by an anomalous specificity in the hydrolysis reaction. By utilizing

  研究了以D-甘露糖为受体的环半芽孢杆菌ATCC 31382（β-1,3-半乳糖苷酶）衍生的β-半乳糖苷酶在反半乳糖基化反应中的区域选择性。发现该D-甘露糖相关的区域选择性不同于使用GlcNAc或GalNAc作为受体的反应，不仅对于β-1,3-半乳糖苷酶而且对于不同来源的β-半乳糖苷酶。在存在β-1,3-半乳糖苷酶的情况下，还测量了具有各种键的Galβ-pNP和D-半乳糖基-D-甘露糖的相对水解速率，发现其与通过转糖基化形成的二糖的比例具有很好的相关性。 。因此，可以通过水解反应中的异常特异性来解释使用D-甘露糖的意外的区域选择性。
• A novel fluorescent assay for T-synthase activity
  作者：T. Ju、B. Xia、R. P. Aryal、W. Wang、Y. Wang、X. Ding、R. Mi、M. He、R. D. Cummings

  DOI：10.1093/glycob/cwq168

  日期：2011.3.1

  Loss of T-synthase (uridine diphosphate galactose:N-acetylgalactosaminyl-α1-Ser/Thr β3galactosyltransferase), a key enzyme required for the formation of mucin-type core 1 O-glycans, is observed in several human diseases, including cancer, Tn syndrome and IgA nephropathy, but current methods to assay the enzyme use radioactive substrates and complicated isolation of the product. Here we report the development of a novel fluorescent assay to measure its activity in a variety of tumor cell lines. Deficiencies in T-synthase activity correlate with mutations in the gene encoding the molecular chaperone Cosmc that is required for folding the T-synthase. This new high-throughput assay allows for facile screening of tumor specimens and other biological material for T-synthase activity and could be used diagnostically.

  T-合成酶（尿苷二磷酸半乳糖: N-乙酰半乳糖胺基-α1-丝氨酸/苏氨酸 β3-半乳糖转移酶）是形成粘蛋白类型核心1 O-糖苷的关键酶，在多种人类疾病中被观察到其缺失，包括癌症、Tn综合症和IgA肾病，但目前检测该酶的方法使用放射性底物并需要复杂的产物分离。在此，我们报告了一种新型荧光检测方法，可以在多种肿瘤细胞系中测量其活性。T-合成酶活性的缺乏与编码分子伴侣Cosmc的基因突变相关，Cosmc对于T-合成酶的折叠至关重要。这种新的高通量检测方法能够方便地筛选肿瘤标本和其他生物材料中的T-合成酶活性，并可用于诊断。
• Synthesis of 2-acetamido-2-deoxy-3-O-β-d-galactopyrano-syl-d-galactose by the sequential use of β-d-galactosidases from bovine testes and escherichia coli
  作者：Lars Hedbys、Elisabet Johansson、Klaus Mosbach、Per-Olof Larsson、Alf Gunnarsson、Sigfrid Svensson

  DOI：10.1016/0008-6215(89)84036-4

  日期：1989.3

  beta-D-Galp-(1----3)-D-GalNAc (1) was synthesised from lactose and GalNAc on a mmolar scale by transgalactosylation using beta-D-galactosidase from bovine testes. The large proportions of unwanted oligosaccharides in the product mixture were removed by treatment with beta-D-galactosidase from E. coli, which left 1, monosaccharides, and a small proportion of trisaccharides. Carbon-Celite chromatography

  使用来自牛睾丸的β-D-半乳糖苷酶经半乳糖基化反应，由乳糖和GalNAc以毫摩尔级合成β-D-Galp-（1 ---- 3）-D-GalNAc（1）。通过用来自大肠杆菌的β-D-半乳糖苷酶处理除去产物混合物中的大部分不需要的寡糖，这留下了1个单糖和一小部分的三糖。然后，基于添加的GalNAc，碳-硅藻土色谱法得到1，产率为21％。
• A process for preparing 3-0-beta-D-galactopyranosyl-2-acetamido-2-deoxy-galactose
  申请人：BIOCARB AB

  公开号：EP0327521A2

  公开（公告）日：1989-08-09

  A process for synthesizing 3-O-β-D-Galactopyranosyl-2-aceta­mido-2-deoxy-galactose (1) by enzymatic transgalactosylation using β-galactosidases, characterized by the steps: a) transgalactosylating a substrate mixture of lactose and 2-acetamido-2-deoxy-D-galactose utilizing the transgalactoly­tic activity possessed by β-galactosidase of mammalian origin to form an olgiosaccharide mixture including (1); b) hydrolysing the mixture resulting from step a) above with a β-galactosidase of microbial origin leaving (1) sub­stantially intact; and c) recovering (1) from the hydrolyzed mixture resulting from step b).

  一种利用β-半乳糖苷酶通过酶促转半乳糖苷化合成3-O-β-D-吡喃半乳糖基-2-乙酰氨基-2-脱氧半乳糖(1)的工艺，其特征在于以下步骤： a) 利用哺乳动物源的β-半乳糖苷酶所具有的转半乳糖分解活性，对乳糖和 2-乙酰氨基-2-脱氧-D-半乳糖的底物混合物进行转半乳糖分解，形成包括（1）的寡糖混合物； b) 用微生物源的β-半乳糖苷酶水解上述步骤 a)产生的混合物，使(1)基本保持完整；以及 c) 从步骤 b) 产生的水解混合物中回收(1)。
• Thermal decomposition of β-d-galactopyranosyl-(1→3)-2-acetamido-2-deoxy-d-hexopyranoses under neutral conditions
  作者：Kazuhiro Chiku、Mamoru Nishimoto、Motomitsu Kitaoka

  DOI：10.1016/j.carres.2010.06.003

  日期：2010.9

  beta-D-Galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-glucose (LNB) and beta-D-galactopyranosyl-(1 -> 3)-2-acetamido-2-deoxy-D-galactose (GNB) decompose rapidly upon heating into D-galactose and mono-dehydrated derivatives of the corresponding 2-acetamido-2-deoxy-D-hexoses, including 2-acetamido-2,3-dideoxy-hex-2-enofuranoses and bicyclic 2-acetamido-3,6-anhydro-2-deoxy-hexofuranoses. The decomposition is conducted under neutral conditions where glycosyl linkages are generally believed to be stable. The half-lives of LNB and GNB were 8.1 min and 20 min, respectively, at 90 degrees C and pH 7.5. The pH dependency of decomposition rates suggests that the instabilities are an extension of the conditions for the peeling reaction, often observed with glycans of O-linked glycoproteins under alkaline conditions. Such decomposition under the neutral conditions is commonly observed with 3-O-linked reducing aldoses. (C) 2010 Elsevier Ltd. All rights reserved.