1-deoxy-1-allyl-2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside | 1092574-83-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-1-allyl-2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside
• 英文别名: allyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside
• CAS: 1092574-83-8
• 化学式: C₃₃H₇₂O₅Si₄
• 分子量: 661.274
• InChiKey: MSYULMAWVFSAEU-UCWKTGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.52
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-deoxy-1-allyl-2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-β-D-galactopyranosyl-1-propene
  参考文献：
  名称：

  Hydration IndexA Better Parameter for Explaining Small Molecule Hydration in Inhibition of Ice Recrystallization

  摘要：

  Several simple mono- and disaccharides have been assessed for their ability to inhibit ice recrystallization. Two carbohydrates were found to be effective recrystallization inhibitors. D-Galactose (1) was the best monosaccharide and D-melibiose (5) was the most active disaccharide. The ability of each carbohydrate to inhibit ice growth was correlated to its respective hydration number reported in the literature. A hydration number reflects the number of tightly bound water molecules to the carbohydrate and is a function of carbohydrate stereochemistry. It was discovered that using the absolute hydration number of a carbohydrate does not allow one to accurately predict its ability to inhibit ice recrystallization. Consequently, we have defined a hydration index in which the hydration number is divided by the molar volume of the carbohydrate. This new parameter not only takes into account the number of water molecules tightly bound to a carbohydrate but also the size or volume of a particular solute and ultimately the concentration of hydrated water molecules. The hydration index of both mono- and disaccharides correlates well with experimentally measured RI activity. C-Linked derivatives of the monosaccharides appear to have RI activity comparable to that of their O-linked saccharides but a more thorough investigation is required. The relationship between carbohydrate concentration and RI activity was shown to be noncolligative and a 0.022 M solution of D-galactose (1) and C-linked galactose derivative (10) inhibited recrystallization as well as a 3% DMSO solution. The carbohydrates examined in this study did not possess any thermal hysteresis activity (selective depression of freezing point relative to melting point) or dynamic ice shaping. As such, we propose that they are inhibiting recrystallization at the interface between bulk water and the quasi liquid layer (a semiordered interface between ice and bulk water) by disrupting the preordering of water.

  DOI：

  10.1021/ja806284x
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 sodium 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 1-deoxy-1-allyl-2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a C-linked Antifreeze Glycoprotein (AFGP) Mimic:  Probes for Investigating the Mechanism of Action

  摘要：

  [GRAPHICS]A general convergent synthesis has been developed to afford a low molecular weight C-linked antifreeze glycoprotein (AFGP) mimic (9). Structural mimics of AFGPs have tremendous potential as probes to better understand how native AFGPs inhibit ice crystal growth in organisms that inhabit subzero environments.

  DOI：

  10.1021/ol991025+

文献信息

• Glycopolypeptides via Living Polymerization of Glycosylated-<scp>l</scp>-lysine <i>N</i>-Carboxyanhydrides
  作者：Jessica R. Kramer、Timothy J. Deming

  DOI：10.1021/ja107425f

  日期：2010.10.27

  arboxyanhydride (glyco-K NCA) monomers is described. These monomers employ C-linked sugars and amide linkages to lysine for improved stability without sacrificing biochemical properties. Three glyco-K NCAs were synthesized, purified, and found to undergo living polymerization using transition metal initiation. These are the first living polymerizations of glycosylated NCAs and were used to prepare

  描述了新的糖基化-L-赖氨酸-N-羧酸酐（糖-K NCA）单体的制备。这些单体使用 C 连接的糖和酰胺键连接到赖氨酸以提高稳定性而不牺牲生化特性。合成、纯化了三种糖基 K NCA，并发现它们使用过渡金属引发进行活性聚合。这些是糖基化 NCA 的首次活性聚合，用于制备定义明确的高分子量糖多肽以及阻断和统计糖多肽。这种方法解决了从 N-羧酸酐直接合成糖多肽中与单体合成、纯化和聚合相关的许多长期存在的问题，并提供了具有 100% 糖基化的多肽。