methyl 2,4-dibromo-2,4-dideoxy-L-threonate | 88824-10-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 2,4-dibromo-2,4-dideoxy-L-threonate
• 英文别名: methyl (2R,3S)-2,4-dibromo-3-hydroxybutanoate
• CAS: 88824-10-6
• 化学式: C₅H₈Br₂O₃
• 分子量: 275.925
• InChiKey: ORUPRZUZWITYDZ-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,4-dibromo-2,4-dideoxy-L-threonate 在 palladium on activated charcoal sodium azide 、 氢气 、 sodium acetate 作用下， 以 溶剂黄146 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 生成 丁酸,4-叠氮-3-羟基-,甲基酯,(3R)-
  参考文献：
  名称：

  Synthesis of S- and R-4-Amino-3-hydroxybutyric Acid (GABOB) and S- and R-Carnitine from Arabinose or Ascorbic Acid.

  摘要：

  DOI：

  10.3891/acta.chem.scand.37b-0341
• 作为产物：
  描述：

  potassium-L-threonate 在 氢溴酸 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以76%的产率得到methyl 2,4-dibromo-2,4-dideoxy-L-threonate
  参考文献：
  名称：

  Compositions and methods for targeted enzymatic release of cell regulatory compounds

  摘要：

  本发明描述了新型前药及其用于改变活细胞、组织或整个生物体的生长和生物学特性的方法。该方法允许在表达激活前药酶基因的转化宿主细胞附近或附近选择性地激活前药。根据本发明的一个优选实施例，前药是生物活性化合物与能够通过酶作用从生物活性化合物中裂解出来的化学基团的缀合物。根据本发明的方法包括：(a)将编码酶的基因引入目标细胞；(b)施用前药，其中酶从前药缀合物中释放前药。在本发明的一个优选实施例中，编码酶的基因是标记基因。

  公开号：

  US06656917B1

文献信息

• Deoxyiminoalditols from Aldonic Acids VI. Preparation of the Four Stereoisomeric 4-Amino-3-hydroxypyrrolidines from Bromodeoxytetronic Acids. Discovery of a New α-Mannosidase Inhibitor
  作者：Gerrit Limberg、Inge Lundt、John Zavilla

  DOI：10.1055/s-1999-3680

  日期：1999.1

  A convenient four step synthesis of 4-amino-3-hydroxy-pyrrolidines is presented. From the readily available d- and l-tetronic acids the four possible stereoisomeric 4-amino-3-hydroxy-pyrrolidines 14 (3R,4R), 15 (3R,4S), ent-14 (3S,4S) and ent-15 (3S,4R) could be obtained as crystalline compounds, avoiding any chromatographic purification. The key step in the reactions was the regioselective formation of either the 2,4-diamino-2,4-di-deoxy-d-threono-1,4-lactam (5) or the 3,4-diamino-3,4-dideoxy-l-erythrono-1,4-lactam (10) by treatment of the methyl 4-bromo-4-deoxy-2,3-cis- or -2,3-trans-anhydrotetronates (3 or 9), respectively, with liquid ammonia. Thus, opposite regioselectivity for the opening of the cis-configurated epoxide 3 (4 : 1, C-2/C-3) and the trans-configurated epoxide 9 (3 : 7, C-2/C-3) by ammonia was observed. Preliminary testing as glycosidase inhibitors of the 4-amino-3-hydroxypyrrolidines formed by reduction of the lactams showed an inhibition of α-mannosidase (Ki 40 μM) by isomer 14, (3R,4R)-4-amino-3-hydroxypyrrolidine.

  提出了 4-氨基-3-羟基-吡咯烷的便​​捷四步合成。从容易获得的 d-和 l-特窗酸中可以得到四种可能的立体异构体 4-氨基-3-羟基-吡咯烷 14 (3R,4R)、15 (3R,4S)、ent-14 (3S,4S) 和 ent-15 (3S,4R)可以作为结晶化合物获得，避免任何色谱纯化。反应的关键步骤是区域选择性形成 2,4-二氨基-2,4-二-脱氧-d-苏酮-1,4-内酰胺 (5) 或 3,4-二氨基-3,4通过分别处理4-溴-4-脱氧-2,3-顺式-或-2,3-反式-脱水四酮酸甲酯(3或9)，得到-二脱氧-L-赤式-1,4-内酰胺(10) ，用液氨。因此，氨对顺式环氧化物 3 (4:1, C-2/C-3) 和反式环氧化物 9 (3:7, C-2/C-3) 的开环具有相反的区域选择性。观察到。作为通过内酰胺还原形成的 4-氨基-3-羟基吡咯烷的糖苷酶抑制剂的初步测试显示异构体 14，(3R,4R)-4-氨基-3-羟基吡咯烷对 α-甘露糖苷酶 (Ki 40 μM) 具有抑制作用。
• Method of altering glycosylation of proteins in response to nojirimycin glucuronide in a plant cell expressing glucuronidase
  申请人：Naleway John J.

  公开号：US08716558B2

  公开（公告）日：2014-05-06

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. Such cells may include animal cells, plant cells and bacterial cells. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene. Methods according to a preferred embodiment of the invention include altering protein production in a plant cell such as altering glycosylation of a protein produced by the plant cell.

  本发明描述了一种新型的前药及其使用方法，用于改变生物细胞、组织或整个生物体的生长和生物学特性。这些细胞可以包括动物细胞、植物细胞和细菌细胞。该方法允许在表达激活前药酶基因的转化宿主细胞附近或附近选择性激活前药。本发明的优选实施方式中，前药是生物活性化合物和能够被酶作用从生物活性化合物中切除的化学基团的结合物。根据本发明的方法包括：（a）将编码酶的基因引入靶向细胞中和（b）给予前药，其中酶释放与前药结合的物质。在本发明的优选实施方式中，编码酶的基因是一个标记基因。根据本发明的优选实施方式，包括改变植物细胞中的蛋白质生产，例如改变植物细胞所产生的蛋白质的糖基化。
• KARANEWSKY, DONALD S.;BILLER, SCOTT A.;GORDON, ERIC M.
  作者：KARANEWSKY, DONALD S.、BILLER, SCOTT A.、GORDON, ERIC M.

  DOI：——

  日期：——
• Compositions and methods for targeted enzymatic release of cell regulatory compounds
  申请人：Marker Gene Technologies, Inc.

  公开号：US06656917B1

  公开（公告）日：2003-12-02

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include, (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.

  本发明描述了新型前药及其用于改变活细胞、组织或整个生物体的生长和生物学特性的方法。该方法允许在表达激活前药酶基因的转化宿主细胞附近或附近选择性地激活前药。根据本发明的一个优选实施例，前药是生物活性化合物与能够通过酶作用从生物活性化合物中裂解出来的化学基团的缀合物。根据本发明的方法包括：(a)将编码酶的基因引入目标细胞；(b)施用前药，其中酶从前药缀合物中释放前药。在本发明的一个优选实施例中，编码酶的基因是标记基因。
• Synthesis of S- and R-4-Amino-3-hydroxybutyric Acid (GABOB) and S- and R-Carnitine from Arabinose or Ascorbic Acid.
  作者：Klaus Bock、Inge Lundt、Christian Pedersen、Igor Gaon、Curt R. Enzell、Kenji Inoue

  DOI：10.3891/acta.chem.scand.37b-0341

  日期：——