methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside | 30589-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside
• 英文别名: 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside；methyl-[tri-O-acetyl-6-bromo-α-D-rhamnopyranoside；Methyl-[tri-O-acetyl-6-brom-α-D-rhamnopyranosid；6-Brom-triacetyl-methyl-α-D-mannopyranosid；[(2S,3S,4S,5S,6S)-4,5-diacetyloxy-2-(bromomethyl)-6-methoxyoxan-3-yl] acetate
• CAS: 30589-67-4
• 化学式: C₁₃H₁₉BrO₈
• 分子量: 383.193
• InChiKey: JEEGQLMJZGMZSR-BNDIWNMDSA-N

物化性质

• 沸点：
  397.2±42.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside 在 三正丁基氢锡 、 sodium methylate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 12.0h， 生成 甲基 6-脱氧-beta-L-吡喃甘露糖苷
  参考文献：
  名称：

  Enzymes in oligosaccharide synthesis: active-domain overproduction, specificity study, and synthetic use of an .alpha.-1,2-mannosyltransferase with regeneration of GDP-Man

  摘要：

  The catalytic domain of a membrane-bound alpha-1,2-mannosyltransferase (ManT) from yeast has been overexpressed in E. coli, at a level of approximately 0.7-0.8 units per L with a specific activity of about 1 U/mg (based on a-methyl mannoside) after purification. The E. coli strain has been deposited in ATCC (#77379) and will be available to the public. The isolated ManT is stable in 30% methanol or 20% acetone. It accepts mannose, mannobiose, and O-mannosylglycopeptides as acceptors. A multiple enzyme system with in situ regeneration of GDP-mannose suitable for large-scale synthesis of mannosides and mannosyl glycopeptides has been developed.

  DOI：

  10.1021/jo00067a035
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Enzymes in oligosaccharide synthesis: active-domain overproduction, specificity study, and synthetic use of an .alpha.-1,2-mannosyltransferase with regeneration of GDP-Man

  摘要：

  The catalytic domain of a membrane-bound alpha-1,2-mannosyltransferase (ManT) from yeast has been overexpressed in E. coli, at a level of approximately 0.7-0.8 units per L with a specific activity of about 1 U/mg (based on a-methyl mannoside) after purification. The E. coli strain has been deposited in ATCC (#77379) and will be available to the public. The isolated ManT is stable in 30% methanol or 20% acetone. It accepts mannose, mannobiose, and O-mannosylglycopeptides as acceptors. A multiple enzyme system with in situ regeneration of GDP-mannose suitable for large-scale synthesis of mannosides and mannosyl glycopeptides has been developed.

  DOI：

  10.1021/jo00067a035

文献信息

• Mannosyl transfer with regeneration of GDP-mannose
  申请人：——

  公开号：US20030119090A1

  公开（公告）日：2003-06-26

  A one-pot glycosylation reaction is disclosed in which a mannosyl (Man) group is enzymatically transferred to an acceptor molecule. The starting glycoside is a mannosyl 1-phosphate that is enzymatically converted to its GDP derivative via UTP and a pyrophorylase. The formed GDP derivative is used in the enzyme-catalyzed glycosyl transfer. That enzyme-catalyzed glycosyl transfer to an acceptor releases GDP that is enzymatically converted to GTP for further conversion of mannosyl 1-phosphate into its GDP derivative. Also disclosed are a recombinant &agr;1,2-mannosyltransferase that is enzymatically active, is dispersible in an aqueous reaction medium, and free of the transmembrane portion of the native enzyme, as well as DNA encoding that transferase, an expression vector containing exogenous DNA that encodes that enzyme and E. coli cells containing that vector.

  本发明公开了一种单锅糖基化反应，在该反应中，甘露糖基（Man）被酶促转移到受体分子上。起始糖苷是甘露糖基 1-磷酸，通过 UTP 和焦磷酸酶酶促转化为 GDP 衍生物。形成的 GDP 衍生物用于酶催化的糖基转移。经酶催化的糖基转移到受体后释放出 GDP，再经酶转化为 GTP，进一步将 1-磷酸甘露糖苷转化为其 GDP 衍生物。还公开了一种重组的&agr;1,2-甘露糖基转移酶，它具有酶活性，可在水性反应介质中分散，不含原生酶的跨膜部分，还公开了编码该转移酶的 DNA、含有编码该酶的外源 DNA 的表达载体和大肠杆菌。 大肠杆菌 细胞。
• Valentin, Collection of Czechoslovak Chemical Communications, 1934, vol. 6, p. 354,368
  作者：Valentin

  DOI：——

  日期：——
• A simple synthesis of sugar disulfides using tetrathiomolybdate as a sulfur-transfer reagent
  作者：Debjani Bhar、Srinivasan Chandrasekaran

  DOI：10.1016/s0008-6215(97)00098-0

  日期：1997.6
• US6485930B1
  申请人：——

  公开号：US6485930B1

  公开（公告）日：2002-11-26
• US6919440B2
  申请人：——

  公开号：US6919440B2

  公开（公告）日：2005-07-19