methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-mannopyranoside | 52290-45-6

• 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-deoxy-α-D-mannopyranoside
• 英文别名: methyl 2,3,4-tri-O-acetyl-α-D-rhamnopyranoside；[(2R,3R,4S,5S,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 52290-45-6
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: RTVWBDNQHISFHI-LDEZANTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  7
• 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-deoxy-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到甲基 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：

  methyl 2,3,4-tri-O-acetyl-6-bromo-6-deoxy-α-D-mannopyranoside 在 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 methyl 2,3,4-tri-O-acetyl-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

• Calcium hypophosphite mediated deiodination in water: mechanistic insights and applications in large scale syntheses of <scp>d</scp>-quinovose and <scp>d</scp>-rhamnose
  作者：Zejin Song、Lingkui Meng、Ying Xiao、Xiang Zhao、Jing Fang、Jing Zeng、Qian Wan

  DOI：10.1039/c8gc03851a

  日期：——

  The inorganic calcium hypophosphite was found to be a cheap, non-toxic, water-soluble and environmentally friendly reducing reagent for radical deiodination in water. Thorough mechanism studies revealed that calcium hypophosphite was oxidized to water insoluble calcium phosphite which was the major co-product of the deiodination reaction. Based on this observation, a practical synthesis of rare D-quinovose

  已发现无机次磷酸钙是一种廉价，无毒，水溶性且环保的还原剂，可用于水中的自由基脱碘。深入的机理研究表明，次磷酸钙被氧化为水不溶性亚磷酸钙，这是脱碘反应的主要副产物。基于该观察结果，报道了从廉价且可商购的材料以一百毫摩尔规模实际合成稀有D-奎诺糖和D-鼠李糖的方法。
• A convenient and general synthesis of 5-vinylhexofuranosides from 6-halo-6-deoxypyranosides
  作者：Masami Nakane、C. Richard Hutchinson、Harold Gollman

  DOI：10.1016/s0040-4039(00)71373-6

  日期：——

  The synthesis of five different 5,6-dideoxyhex-5-enofuranosides (5, 7, 9 and 11) proceeds in 30–60% overall yield in two steps from commercially available 1-0-methyl pyranosides by reductive β-elimination of the intermediate 6-bromo-6-deoxypyranosides.

  通过还原性的β-消除作用，从市售的1-0-甲基吡喃糖苷中分两步合成了5种不同的5,6-二脱氧己基-5-烯呋喃糖苷（5、7、9和11），总产率为30-60％。中间体6-溴-6-脱氧吡喃糖苷。
• Synthesis of modified D-mannose core derivatives and their impact on GH38 α-mannosidases
  作者：Monika Poláková、Radim Horák、Sergej Šesták、Ivana Holková

  DOI：10.1016/j.carres.2016.04.004

  日期：2016.6

  Nine new compounds having five- and modified six-member carbohydrate core derived from D-lyxose or D-mannose, and non-hydrolysable aglycones (benzylsulfonyl or aryl(alkyl)triazolyl) were synthesised to investigate their ability to inhibit the recombinant Drosophila melanogaster homologs of two human GH38 family enzymes: Golgi mannosidase II (dGMIIb) and lysosomal mannosidase (dLMII). Two compounds

  合成了九种新化合物，这些化合物具有衍生自D-lyxose或D-甘露糖的五元和六元碳水化合物核心，以及不可水解的糖苷配基（苄基磺酰基或芳基（烷基）三唑基），以研究其抑制重组果蝇果蝇同系物的能力。两种人类GH38家族酶中的一种：高尔基甘露糖苷酶II（dGMIIb）和溶酶体甘露糖苷酶（dLMII）。两种化合物是弱选择性dGMIIb抑制剂，在mM水平下显示IC50。此外，发现另一种GH38酶，商品菜豆α-甘露糖苷酶，无论碳水化合物核心如何，都被三唑缀合物抑制，而相应的砜是无活性的。
• 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。
• Niggemann, Jutta; Thiem, Joachim, Liebigs Annalen der Chemie, 1992, # 5, p. 535 - 538
  作者：Niggemann, Jutta、Thiem, Joachim

  DOI：——

  日期：——