6-azido-6-deoxy-α-D-galactopyranose | 73174-38-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-α-D-galactopyranose
• 英文别名: 6-azido-6-deoxy-D-galactose；6-Azido-6-deoxy-alpha-D-galactopyranose；(2S,3R,4S,5R,6R)-6-(azidomethyl)oxane-2,3,4,5-tetrol
• CAS: 73174-38-6
• 化学式: C₆H₁₁N₃O₅
• 分子量: 205.17
• InChiKey: CMLRUUHRGSJVMD-PHYPRBDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 6-azido-6-deoxy-α-D-galactopyranose 在 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以60%的产率得到6-amino-6-deoxy-α-D-galactopyranose 6,4-(cyclic carbamate)
  参考文献：
  名称：

  Unprotected sugar phosphinimines: A facile route to cyclic carbamates of amino sugars

  摘要：

  DOI：

  10.1016/s0008-6215(00)90755-9
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-6-O-trifluoromethanesulfonyl-α-D-galactopyranose 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 6-azido-6-deoxy-α-D-galactopyranose
  参考文献：
  名称：

  叠氮基-脱氧和氨基-脱氧糖苷和糖基氟化物的合成，用于筛选糖苷酶文库和组装取代的糖苷。

  摘要：

  叠氮化物和胺取代的糖在探测生物系统以及使用点击化学或简单的胺偶联方法组装衍生物库中可能是有用的工具。通过叠氮化物置换相应的三氟甲磺酸衍生物并随后进行修饰，合成了葡萄糖，半乳糖和木糖的各种叠氮基和氨基脱氧糖衍生物的甲基伞形糖苷苷。这些化合物将在高通量筛选中用作底物，以鉴定可加工此类修饰糖的糖苷酶。还合成了每种修饰糖的α-糖基氟衍生物，以用作衍生自筛选中鉴定的酶的糖合酶底物。

  DOI：

  10.1016/j.carres.2018.07.007

文献信息

• The New Pharmacological Chaperones PBXs Increase α-Galactosidase A Activity in Fabry Disease Cellular Models
  作者：Pedro Besada、María Gallardo-Gómez、Tania Pérez-Márquez、Lucía Patiño-Álvarez、Sergio Pantano、Carlos Silva-López、Carmen Terán、Ana Arévalo-Gómez、Aurora Ruz-Zafra、Julián Fernández-Martín、Saida Ortolano

  DOI：10.3390/biom11121856

  日期：——

  Fabry disease is an X-linked multisystemic disorder caused by the impairment of lysosomal α-Galactosidase A, which leads to the progressive accumulation of glycosphingolipids and to defective lysosomal metabolism. Currently, Fabry disease is treated by enzyme replacement therapy or the orally administrated pharmacological chaperone Migalastat. Both therapeutic strategies present limitations, since enzyme replacement therapy has shown low half-life and bioavailability, while Migalastat is only approved for patients with specific mutations. The aim of this work was to assess the efficacy of PBX galactose analogues to stabilize α-Galactosidase A and therefore evaluate their potential use in Fabry patients with mutations that are not amenable to the treatment with Migalastat. We demonstrated that PBX compounds are safe and effective concerning stabilization of α-Galactosidase A in relevant cellular models of the disease, as assessed by enzymatic activity measurements, molecular modelling, and cell viability assays. This experimental evidence suggests that PBX compounds are promising candidates for the treatment of Fabry disease caused by mutations which affect the folding of α-Galactosidase A, even for GLA variants that are not amenable to the treatment with Migalastat.

  法布里病是一种X连锁多系统障碍，由溶酶体α-半乳糖苷酶A的损伤引起，导致糖脂代谢的进行受到影响和逐渐积累。目前，法布里病的治疗方法包括酶替代疗法和口服药物MigaLAstat。这两种治疗策略都存在局限性，因为酶替代疗法的半衰期和生物利用度较低，而MigaLAstat只适用于特定基因突变的患者。本研究的目的是评估PBX半乳糖类似物稳定α-半乳糖苷酶A的功效，从而评估它们在无法使用MigaLAstat治疗的法布里病患者中的潜在用途。我们证明PBX化合物在疾病相关细胞模型中稳定α-半乳糖苷酶A是安全和有效的，通过酶活性测量、分子建模和细胞存活率检测进行评估。这些实验证据表明，PBX化合物是治疗因α-半乳糖苷酶A折叠受影响而引起的法布里病的有希望的候选药物，即使对于不适用于MigaLAstat治疗的GLA变异体也是如此。
• Modified Proteins
  申请人：Behrens Carsten

  公开号：US20080108557A1

  公开（公告）日：2008-05-08

  A method of conjugating peptides and proteins by means of glycosyltransferase is provided.

  提供了一种通过糖基转移酶结合肽和蛋白质的方法。
• MODIFIED CARBOHYDRATE PROCESSING ENZYME
  申请人：Davis Benjamin G.

  公开号：US20090181444A1

  公开（公告）日：2009-07-16

  A modified polypeptide having carbohydrate processing enzymatic activity is provided, said polypeptide comprising an amino acid sequence selected from: (a) the amino acid sequence of SEQ ID NO:2 comprising a mutation in at least one of W433, E432 and M439; (b) the amino acid sequence of an enzyme of glycosyl hydrolase family 1, comprising at least one mutation at an amino acid residue equivalent to W433, E432 or M439 of SEQ ID NO:2; and (c) a variant of (a) or (b) having carbohydrate processing enzymatic activity and comprising at least one amino acid mutation at a position equivalent to W433, E432 or M439 of SEQ ID NO:2.

  提供一种具有碳水化合物加工酶活性的改性多肽，该多肽包括以下氨基酸序列之一：(a) SEQ ID NO: 2的氨基酸序列，其中至少有一个W433、E432和M439突变；(b) 包括至少一个氨基酸残基等同于SEQ ID NO:2的W433、E432或M439的糖基水解酶家族1酶的氨基酸序列；以及(c) 具有碳水化合物加工酶活性的(a)或(b)的变体，其中包括至少一个氨基酸突变位于等同于SEQ ID NO:2的W433、E432或M439的位置。
• Metallization of Double-Stranded DNA Triggered by Bound Galactose-Modified Naphthalene Diimide
  作者：Kohei Komizo、Hideyuki Ikedo、Shinobu Sato、Shigeori Takenaka

  DOI：10.1021/bc500263b

  日期：2014.8.20

  Naphthalene diimide (NDI) derivatives bearing galactose moieties through different spacers, NDI-DS1 and NDI-DS2, were synthesized by the click reaction of the acetylene derivatives of NDI with galactose azide. They bound to double-stranded DNA with threading intercalation, as confirmed by the topoisomerase I assay and circular dichroism spectroscopy. The binding affinities of these ligands were on the order of 10(5) M-1 with several-fold higher affinity for double-stranded DNA than for single-stranded DNA. The silver mirror reaction on the double-stranded DNA bound to these ligands afforded silver nanowires that were converted to gold nanowires. In the atomic force microscopy measurements, the increased height of DNA areas on a mica plate was observed in the case of double-stranded DNA after NDI-DS2 treatment and subsequently silver mirror reaction, whereas the increased height of DNA areas was not observed in the case of single-stranded DNA after the same treatment.
• THERAPEUTIC COMPOUNDS
  申请人：Oxford GlycoSciences (UK) Limited

  公开号：EP0946581A1

  公开（公告）日：1999-10-06