8-methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-glucopyranoside | 65567-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: methyl 9-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 65567-18-2
• 化学式: C₁₈H₃₃NO₈
• 分子量: 391.462
• InChiKey: VPMCTXJWSFZZCE-JVNHZCFISA-N

物化性质

• 沸点：
  608.8±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 氰化汞 、 对甲苯磺酸 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  O-α-L-鼠李糖吡喃糖基-（1进入3）-O-α-L-鼠李糖吡喃糖基-（1进入3）-2-乙酰氨基-2,6-的8-（甲氧羰基）辛基糖苷的合成双脱氧-D-吡喃葡萄糖; 铜绿假单胞菌Fisher免疫型5抗原模型。

  摘要：

  DOI：

  10.1016/s0008-6215(82)80027-x
• 作为产物：
  描述：

  D-GlcNAc 在 calcium sulfate 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 苯 为溶剂， 反应 99.0h， 生成 8-methoxycarbonyloctyl 2-acetamido-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Evaluation of Homoaza Sugars as Glycosidase Inhibitors

  摘要：

  In an effort to develop transition-state mimetics of the glycosidase-catalyzed reaction, five- and six-membered azasugars and their home-analogs were prepared and tested as inhibitors of glycosidases. Inhibition studies indicate that the fucosyl cationlike, five-membered imine 1 and its reduced form 2 are potent inhibitors of alpha-fucosidase from bovine kidney with respective K-i values of 160 nM and 2 mu M. The five-membered homoaminoazasugar 3 is also a potent inhibitor of the enzyme (K-i = 1.9 x 10(-6) M), while the glucose and mannose-like six-membered homoaminoazasugars 4 and 5 are less potent than the corresponding 1-deoxyazasugars as inhibitors of alpha-glucosidase and alpha-mannosidase, respectively. The primary amino group was placed in an attempt to introduce additional electrostatic interactions in the active site. The inhibitory activities are, however, in the high mu M range. Synthesis of homoazasugars structurally related to a disaccharide and a nucleoside is also described.

  DOI：

  10.1021/jo00111a007

文献信息

• Processes for the synthesis of sialyl Lewis.sup.x compounds
  申请人：Glycomed Incorporated

  公开号：US05654412A1

  公开（公告）日：1997-08-05

  Disclosed are processes for the chemical synthesis of sialyl Lewis.sup.x -Y compounds where Y is --OH, --NHR, --SH, --SR or --OR, and R is an aglycon of at least one carbon atom.

  揭示了一种化学合成唾液酸基Lewis.sup.x -Y化合物的方法，其中Y为--OH、--NHR、--SH、--SR或--OR，而R是至少含有一个碳原子的糖基。
• Chemical synthesis and kinetic characterization of UDP-2-deoxy-d-lyxo-hexose(“UDP-2-deoxy-d-galactose”), a donor-substrate for β-(1 → 4)-d-galactosyltransferase
  作者：Geeta Srivastava、Ole Hindsgaul、Monica M. Palcic

  DOI：10.1016/0008-6215(93)80066-n

  日期：1993.7

  here the chemical synthesis, structural characterization and enzymatic evaluation of the very labile UDP-2-deoxy-D-lyxo-hexose ("UDP-2-deoxy-galactose," 2) as an alternate donor for GalT. Donor 2 had kinetic parameters, including a Km value of 51 microM, almost identical to those for the natural substrate UDP-galactose when beta-D-GlcpNAc-O(CH2)8COOMe was used as the acceptor. The product of the enzymatic

  牛β-（1→4）-半乳糖基转移酶（GalT）将半乳糖从UDP-半乳糖转移至以β-D-GlcpNAc为末端的寡糖，以产生N-乙酰基乳糖胺序列。我们在这里报告了非常不稳定的UDP-2-脱氧-D-lyxo-己糖（“ UDP-2-脱氧-半乳糖，” 2）作为GalT的供体的化学合成，结构表征和酶促评估。当β-D-GlcpNAc-O（CH2）8COOMe被用作受体时，供体2的动力学参数包括Km值为51 microM，几乎与天然底物UDP-半乳糖的动力学参数相同。分离出酶促转移的产物，并确认其具有预期的2'-脱氧-N-乙酰基乳糖胺序列。
• Synthesis of type 2 human blood-group antigenic determinants. The H, X, and Y haptens and variations of the H type 2 determinant as probes for the combining site of the lectin I of Ulex europaeus
  作者：Ole Hindsgaul、Thomas Norberg、Jacques Le Pendu、Raymond U. Lemieux

  DOI：10.1016/0008-6215(82)84034-2

  日期：1982.11

  Chemical syntheses of the human blood-group antigenic determinants derived from N-acetyllactosamine are described; namely, the 6-deoxy derivative, the 4'-epimer, and the 5 H type 2 [alpha LFuc(1 to 2)beta DGal-(1 to 4)beta DGlcNAc], X [beta DGal(1 to 4)[alpha LFuc(1 to 3)[beta DGlcNAc], and Y [alpha LFuc-(1 to 2)beta DGal(1 to 4)[alpha LFuc(1 to 3)]beta DGlcNAc] determinants as glycosides of 8-carboxymethyloctanol

  描述了衍生自N-乙酰基乳糖胺的人血型抗原决定簇的化学合成。即6-脱氧衍生物，4'-末端和5 H 2型[αLFuc（1至2）beta DGal-（1至4）beta DGlcNAc]，X [beta DGal（1至4）[ αLFuc（1至3）βDGlcNAc和Y [αLFuc-（1至2）βDGal（1至4）[αLFuc（1至3）]βDGlcNAc]决定基为8-羧甲基辛醇的糖苷。为了研究H 2决定簇与欧洲油菜的凝集素I的结合，还设计了专门改变H 2决定簇的亲水和疏水部分的结构。即6-脱氧衍生物，4'-末端和5“-正同源物。这些结构的使用，连同H 1型半抗原和H 1型和H 2型决定簇的N-去乙酰化形式一起，作为凝集素对O红细胞凝集的抑制剂，可以得出以下结论：H 2决定簇的结合是疏水性 结合涉及行列式分子的楔形部分，该楔形部分基本上是疏水性的，除了在楔形尖端处的5-羟甲基基团外，与O-5形成分子内氢
• Rapid Conversion of Unprotected Galactose Analogs to their Udp-Derivatives For Use in the Chemo-Enzymatic Synthesis of Unnatural Oligosaccharides
  作者：Taketo Uchiyama、Ole Hindsgaul

  DOI：10.1080/07328309808001892

  日期：1998.11

  The rapid conversion of D-galactose, its 2-deoxy, 3-deoxy, 4-deoxy and 6-deoxy derivatives and L-arabinose to their UDP-derivatives (2-7) is described. The procedure involves the in situ preparation of the per-O-trimethylsilylated glycopyranosyl iodides and their direct reaction with UDP. All six sugar nucleotides were active as substrates for beta(1-->4)-galactosyltransferase and were used to enzymatically prepare N-acetyllactosamine (8) and five of its analogs (9-13).
• Synthesis and photolytic activation of 6″-O-2-nitrobenzyl uridine-5′-diphosphogalactose: a ‘caged’ UDP-Gal derivative
  作者：Karin Mannerstedt、Ole Hindsgaul

  DOI：10.1016/j.carres.2008.01.021

  日期：2008.4

  Placing an 2-nitrobenzyl group on O-6 of the galactosyl residue in uridine-5'-diphosphogalactose (UDP-Gal) gives 6 ''-O-2-nitrobenzyl-UDP-Gal that is shown to be inactive as a donor substrate for beta-(1 -> 4)-galactosyltransferase (GalT). On irradiation at 365 nm, the nitrobenzyl group is completely removed yielding native UDP-Gal that then transfers normally to produce the expected beta Gal-(1 -> 4)-beta GlcNAc disaccharidic linkage. 6 ''-O-2-Nitrobenzyl-UDP-Gal thus fulfils the minimum requirements of a 'caged' UDP-Gal for application in time-resolved crystallographic studies of beta-(1 -> 4)-GalT. (C) 2008 Elsevier Ltd. All rights reserved.