β-D-galactopyranosyl-(1->4)-α-D-mannopyranose | 101312-82-7

• 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)-α-D-mannopyranose
• 英文别名: β-lactose；β-galactopyranosyl-(1->4)-α-D-mannopyranose；Gal1-4β-Man；β-D-galactopyranosyl-(1->4)-D-mannopyranose；O⁴-β-D-Galactopyranosyl-α-D-mannopyranose；4-O-β-D-galactopyranosyl-D-mannopyranose；4-O-beta-galactopyranosyl-D-mannopyranose；epilactose；beta-D-Gal-(1->4)-alpha-D-Man；(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 101312-82-7
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: GUBGYTABKSRVRQ-LVIVMJSQSA-N

物化性质

• 沸点：
  667.9±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 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：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  sodium pyruvate 、 β-D-galactopyranosyl-(1->4)-α-D-mannopyranose 在 盐酸 、 三羟甲基氨基甲烷 作用下， 反应 24.0h， 以38%的产率得到sodium β-D-galactopyranosyl-(1->7)-3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonate
  参考文献：
  名称：

  二糖为唾液酸醛缩酶底物：在还原端含有唾液酸的二糖的合成。

  摘要：

  DOI：

  10.1002/anie.200604799
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 氢溴酸 、 sodium carbonate 、 copper(II) sulfate 、 溶剂黄146 、 间氯过氧苯甲酸 、 锌 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 4.0h， 生成 β-D-galactopyranosyl-(1->4)-α-D-mannopyranose
  参考文献：
  名称：

  Synthesis of the phosphodisaccharide repeat of antigenic lipophosphoglycan of Leishmania donovani parasite

  摘要：

  Synthesis of the immunologically important and structurally unusual phosphodisaccharide repeat unit (Galp1,4 beta-Manp-1 alpha-phosphate) of the lipophosphoglycan cell surface GPI molecule of the protozoan parasite Leishmania donovani has been carried out using lactose as the starting material. The synthesis provides a short and stereoselective route for the preparation of this phosphosaccharide in a preparative scale. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00231-2

文献信息

• 1-Oxabicyclic β-lactams as new inhibitors of elongating MPT–a key enzyme responsible for assembly of cell-surface phosphoglycans of Leishmania parasite
  作者：Dipali Ruhela、Patrali Chatterjee、Ram A. Vishwakarma

  DOI：10.1039/b418247b

  日期：——

  New iminosugars (1-oxabicyclic β-lactam disaccharides) have been synthesized as inhibitors of elongating α-D-mannosyl phosphate transferase (eMPT), a key enzyme involved in the iterative biosynthesis of cell-surface phosphoglycans of the Leishmania parasite. The design is based on a transition-state model for this remarkable enzyme that transfers intact α-D-mannosyl-phosphate from GDP-Man. Since these phosphoglycans are unique to Leishmania and are essential for its infectivity and survival, their biosynthetic pathway has emerged as a novel target for anti-leishmanial drug and vaccine design.

  我们合成了新的亚氨基糖（1-氧代双环δ²-内酰胺二糖），作为拉长δ±-D-甘露糖基磷酸转移酶（eMPT）的抑制剂，eMPT 是一种参与利什曼寄生虫细胞表面磷聚糖迭代生物合成的关键酶。该设计基于这种从 GDP-Man 转移完整 δ±-D-mannosyl-phosphate 的非凡酶的过渡状态模型。由于这些磷聚糖是利什曼原虫特有的，对其感染性和存活至关重要，因此它们的生物合成途径已成为抗利什曼原虫药物和疫苗设计的新目标。
• Präparat zur Wirkstoffapplikation in Kleinsttröpfchenform
  申请人：Cevc, Gregor, Prof. Dr.

  公开号：EP0475160A1

  公开（公告）日：1992-03-18

  Die Erfindung betrifft ein Präparat zur Applikation von Wirkstoffen in Form kleinster, insbesondere mit einer membranartigen Hülle aus einer oder wenigen Lagen amphiphiler Moleküle bzw. mit einer amphiphilen Trägersubstanz versehenen Flüssigkeitströpfchen, insbesondere zum Transport des Wirkstoffes in und durch natürliche Barrieren und Konstriktionen wie Häute und dergleichen. Das Präparat weist einen Gehalt einer randaktiven Substanz auf, der bis zu 99 Mol.-% des Gehaltes dieser Substanz entspricht, durch den der Solubilisierungspunkt der Tröpfchen erreicht wird. Das Präparat eignet sich zur nichtinvasiven Verabreichung von Antidiabetica, insbesondere von Insulin. Die Erfindung betrifft außerdem ein Verfahren zur Herstellung solcher Präparate.

  本发明涉及一种以微小液滴形式施用活性物质的制剂，特别是具有一层或几层两亲性分子或两亲性载体物质的膜状包膜，尤其是用于将活性物质输送到或通过皮肤等天然屏障和收缩物。制剂中边缘活性物质的含量最高可达 99 摩尔%，从而达到液滴的溶解点。该制剂适用于非侵入性给药抗糖尿病药物，特别是胰岛素。本发明还涉及生产这种制剂的工艺。
• Immunomodulating compositions and uses therefor
  申请人：Ralph, Stephen John

  公开号：EP2591786A1

  公开（公告）日：2013-05-15

  The present invention discloses immunomodulating compositions. More particularly, the present invention discloses compositions comprising an immune-modulating agent and a lectin-interactive agent, which are useful for stimulating and prolonging host immune cell responses. The compositions of the present invention are particularly useful in the treatment and/or prophylaxis of a range of conditions including pathogenic infections, autoimmune diseases, transplant rejection, graft versus host disease, allergies, inflammatory disease, as well as cancers and tumours.

  本发明公开了免疫调节组合物。更具体地说，本发明公开了包含免疫调节剂和凝集素活性剂的组合物，这些组合物有助于刺激和延长宿主免疫细胞反应。本发明的组合物特别适用于治疗和/或预防一系列疾病，包括病原体感染、自身免疫性疾病、移植排斥反应、移植物抗宿主疾病、过敏、炎症性疾病以及癌症和肿瘤。
• Protein particles for therapeutic and diagnostic use
  申请人：——

  公开号：US20020142046A1

  公开（公告）日：2002-10-03

  Albumin particles in the nanometer and micrometer size range in an aqueous suspension are rendered stable against resolubilization without the aid of a cross-linking agent and witout denaturation, by the incorporation of a stabilizing agent in the particle composition. Stabilizing agents disclosed include reducing agents, oxdizing agents, hydrogen-accepting molecules, high molecular weight polymers, and sulfur-containing ring compounds. Also disclosed are fibrinogen-coated particles, cross-linked or non-cross-linked, and their use as co-aggregants with platelets and with themselves for purposes of shortening bleeding time and enhancing the effect of thrombin.

  通过在颗粒组合物中加入稳定剂，可使水悬浮液中纳米和微米大小的白蛋白颗粒在不借助交联剂和不发生变性的情况下稳定地防止溶解。已公开的稳定剂包括还原剂、氧化剂、氢接受分子、高分子量聚合物和含硫环化合物。此外，还公开了交联或非交联的纤维蛋白原涂层微粒，以及它们作为与血小板和自身的共聚物的用途，以达到缩短出血时间和增强凝血酶效果的目的。
• Iterative Synthesis of <i>Leishmania</i> Phosphoglycans by Solution, Solid-Phase, and Polycondensation Approaches without Involving Any Glycosylation
  作者：Dipali Ruhela、Ram A. Vishwakarma

  DOI：10.1021/jo0341867

  日期：2003.5.1

  A general strategy (solution, solid-phase, and polycondensation) for the synthesis of antigenic phosphoglycans (PG) of the protozoan parasite Leishmania is presented. Phosphoglycans constitute the variable structural and functional domain of major cell-surface lipophosphoglycan (LPG) and secreted proteophosphoglycan (PPG), the molecules involved in infectivity and survival of the Leishmania parasite inside human macrophages. We have shown that the chemically labile, anomerically phosphodiester-linked phosphoglycan repeats can be assembled in an iterative and efficient manner from a single key intermediate, without involving any glycosylation steps. Furthermore, the phosphoglycan chain can be extended toward either the nonreducing (6'-OH) or the reducing (1-OH) end. We also describe a new and efficient solid-phase methodology to construct phosphoglycans based on design and application of a novel cis-allylphosphoryl solid-phase linker that enabled the selective cleavage of the first anomeric-phosphodiester linkage without affecting any of the other internal anomeric-phosphodiester groups of the growing PG chain on the solid support. The strategy to construct larger phosphoglycans in a one-pot synthesis by polycondensation of a single key intermediate is also described, enabling CD spectrometric measurements to show the helical nature of phosphoglycans. Our versatile synthetic approach provides easy access to Leishmania phosphoglycans and the opportunity to address key immunological, biochemical, and biophysical questions pertaining to the phosphoglycan family (LPG and PPG) unique to the parasite.