2-乙酰氨基-2-脱氧-3-o-(beta-d-氟代半乳糖)-d-吡喃葡萄糖 | 50787-09-2

• 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: 2-乙酰氨基-2-脱氧-3-o-(beta-d-氟代半乳糖)-d-吡喃葡萄糖
• 中文别名: 2-乙酰氨基-2-脱氧-3-O-(BETA-D-氟代半乳糖)-D-吡喃葡萄糖
• 英文名称: lacto-N-biose I
• 英文别名: β-Galp-(1->3)-GlcNAc；Galβ1-3GlcNAc；2-acetylamino-O³-β-D-galactopyranosyl-2-deoxy-D-glucose；2-Acetylamino-O³-β-D-galactopyranosyl-2-desoxy-D-glucose；N-((2R,3R,4R,5R)-4,5,6-Trihydroxy-1-oxo-3-(((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexan-2-yl)acetamide；N-[(2R,3R,4R,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: 50787-09-2
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: QCQYVCMYGCHVMR-ZBELOFFLSA-N

物化性质

• 熔点：
  165-167°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

制备方法与用途

乳糖-N-二糖I(Galβ1-3GlcNAc)是一种内源性代谢产物，是幽门螺杆菌α1,2-岩藻糖基转移酶的受体。

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-2-脱氧-3-o-(beta-d-氟代半乳糖)-d-吡喃葡萄糖 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 6.0h， 生成 2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-D-glucitol
  参考文献：
  名称：

  NMR assignments for glucosylated and galactosylated N-acetylhexosaminitols: oligosaccharide alditols related to O-linked glycans from the protozoan parasite Trypanosoma cruzi

  摘要：

  We report full H-1 and C-13 NMR assignments for 13 gluco- or galacto-pyranosylated derivatives of GlcNAc-ol, GalNAc-ol or ManNAc-ol, many of which have been prepared by enzymatic methods. These spectra are reference data to aid the structural analysis by NMR spectroscopy of glycosylated alditols derived from the mucin of the protozoan parasite Trypanosoma cruzi. A series of structural reporter groups for the derivatives from this unusual series of O-glycans are described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00107-5
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 UDP-glucose 4-epimerase 、 UDP-glucose-hexose-1-phosphate uridylyltransferase 、 lacto-N-biose phosphorylase 作用下， 生成 2-乙酰氨基-2-脱氧-3-o-(beta-d-氟代半乳糖)-d-吡喃葡萄糖
  参考文献：
  名称：

  Practical Preparation of Lacto-N-biose I, a Candidate for the Bifidus Factor in Human Milk

  摘要：

  研究人员展示了一种单锅酶促反应生成乳-N-生物糖 I（LNB）的方法，这种反应被认为代表了母乳低聚糖中的双歧因子。在最初含有 660 毫摩尔蔗糖和 600 毫摩尔 GlcNAc 的 10 升反应混合物中，通过四种酶（蔗糖磷酸化酶、UDP-葡萄糖-己糖-1-磷酸尿苷酰转移酶、UDP-葡萄糖 4-epimerase、乳-N-生物糖磷酸化酶）的同时作用，在 UDP-Glc 和磷酸盐的存在下生成了约 500 毫摩尔的 LNB，表明反应产率为 83%。酵母处理后，通过结晶从混合物中分离出 LNB。最后，经过重结晶，回收了 1.4 千克纯度为 99.6% 的 LNB。

  DOI：

  10.1271/bbb.70320

文献信息

• 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.
• Allessandrini et al., Journal of Biological Chemistry, 1956, vol. 220, p. 71,75
  作者：Allessandrini et al.

  DOI：——

  日期：——
• Kuhn et al., Chemische Berichte, 1954, vol. 87, p. 289
  作者：Kuhn et al.

  DOI：——

  日期：——
• GENE EXPRESSING A BIFIDOBACTERIUM SURFACE-PRESENTED FUSION PROTEIN
  申请人：Shirakawa Toshiro

  公开号：US20120177687A1

  公开（公告）日：2012-07-12

  According to the present invention, there is provided a means of expressing and displaying a protein on the cell surface of a bifidobacterium. In the gene for expressing a protein on the surface of a bifidobacterium of the present invention, a gene coding for a bifidobacterium -derived GNB/LNB substrate-binding membrane protein and a gene coding for the target protein or peptide are linked in this order from the 5′ end side. Thus, a bifidobacterium transformed by introducing the gene for expressing a protein on the surface of a bifidobacterium of the present invention expresses the target protein or peptide on the surface thereof. When the target protein or peptide is an antigen protein or an antigen peptide, the transformed bifidobacterium of the present invention is useful as an oral vaccine.
• US8354113B2
  申请人：——

  公开号：US8354113B2

  公开（公告）日：2013-01-15