2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetic acid | 193156-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetic acid
• 英文别名: carboxymethyl tetraacetyl galactoside；2-(2,3,4,6-tetra-O-acetylated-1-deoxy-α-D-galactopyranosyl)-ethanoic acid；2,3,4,6-tetra-O-acetyl-α-D-galactopyranosylacetic acid；2-[(2R,3S,4R,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]acetic acid
• CAS: 193156-89-7
• 化学式: C₁₆H₂₂O₁₁
• 分子量: 390.344
• InChiKey: QMDHNPNDVMZVMN-DMVVEVTLSA-N

物化性质

• 沸点：
  492.1±35.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective synthesis of neo-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions

  摘要：

  Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00255-2
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 potassium permanganate 、 sodium dihydrogenphosphate 、 三氟化硼乙醚 、 臭氧 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 生成 2-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)acetic acid
  参考文献：
  名称：

  Stereoselective synthesis of neo-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions

  摘要：

  Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00255-2

文献信息

• Synthesis and evaluation of linear CuAAC-oligomerized antifreeze neo-glycopeptides
  作者：Steffen van der Wal、Chantelle J. Capicciotti、Stamatia Rontogianni、Robert N. Ben、Rob M. J. Liskamp

  DOI：10.1039/c4md00013g

  日期：——

  An azido/alkyne-containing glycopeptide monomer was synthesized and CuAAC-oligomerized to obtain a triazole-containing antifreeze glycopeptide analogue with moderate antifreeze activity.

  合成了一种含有偶氮/炔基的糖肽单体，并进行CuAAC寡聚化，得到一种含有三唑基的抗冻糖肽类似物，具有中等抗冻活性。
• Developing highly active small molecule ice recrystallization inhibitors based upon C-linked antifreeze glycoprotein analogues
  作者：John F. Trant、Robyn A. Biggs、Chantelle J. Capicciotti、Robert N. Ben

  DOI：10.1039/c3ra43835j

  日期：——

  Ice recrystallization during cryopreservation results in a significant amount of cellular damage making compounds that exhibit ice recrystallization inhibition (IRI) activity desirable as a novel class of cryoprotectants. Herein, we report a systematic structure–function study on a previously identified IRI active C-linked antifreeze glycoprotein (C-AFGP) analogue (1). These studies indicate that while C-AFGPs containing three tripeptide repeats exhibit weak IRI activity 5.5 μM, a minimum number of four tripeptide repeats is required for potent IRI activity at this concentration. In addition, the galactosyl–ornithine building block 5 exhibited only moderate activity at 22 mM, but IRI activity was significantly increased upon addition of two glycine units to the C-terminal end of the amino acid bearing the C-linked galactopyranose residue. Finally, we report that conjugation of long alkyl chains (octyl, nonyl and decyl) to the C-linked galactosyl moiety of 1 can furnish IRI active small molecules. The “ideal” hydrocarbon chain length was 10 carbons for potent activity in this series of compounds. Longer hydrocarbon chain lengths dramatically decreased solubilities. The results of this study emphasize the importance of hydrophobic moieties for IRI activity and while consistent with previously reported small molecule carbohydrate-based and lysine-based ice recrystallization inhibitors, is the first example where a large IRI active glycoconjugate has been successfully truncated to small molecule IRI active components.

  冰晶再结晶在冷冻保存过程中会造成显著的细胞损伤，使得展现冰晶再结晶抑制（IRI）活性的化合物成为一种新型冷冻保护剂的理想选择。在此，我们报告了一项对先前鉴定的C-连接抗冻糖蛋白（C-AFGP）类似物（1）的系统结构-功能研究。这些研究表明，虽然含有三个肽链重复单元的C-AFGP展现出弱的IRI活性（5.5 μM），但在此浓度下，要求至少四个肽链重复单元以展现强效的IRI活性。此外，半乳糖苷-鸟氨酸构建块5在22 mM时仅表现出中等活性，但当将两个甘氨酸单元添加到带有C-连接半乳糖吡喃糖基残基的氨基酸的C末端时，IRI活性显著增加。最后，我们报告将长烷基链（辛基、壬基和癸基）连接到1的C-连接半乳糖基部分可以生成具有IRI活性的低分子化合物。在这一系列化合物中，"理想"的烃链长度为10个碳，以展现强效活性。更长的烃链长度显著降低了溶解度。本研究的结果强调了疏水基团对IRI活性的关键重要性，虽然与先前报告的基于小分子碳水化合物和赖氨酸的冰晶再结晶抑制剂一致，但这是首次成功将大型IRI活性糖缀合物截短至小分子IRI活性成分的例子。
• 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。
• Solution Conformation of C-Linked Antifreeze Glycoprotein Analogues and Modulation of Ice Recrystallization
  作者：Roger Y. Tam、Christopher N. Rowley、Ivan Petrov、Tianyi Zhang、Nicholas A. Afagh、Tom K. Woo、Robert N. Ben

  DOI：10.1021/ja904169a

  日期：2009.11.4

  simulations did indicate that the side chain of IRI-active analogue 26 (n = 3) adopts a unique short-range solution conformation in which it is folded back onto the peptide backbone, orienting the more hydrophilic face of the carbohydrate moiety away from the bulk solvent. In contrast, the solution conformation of IRI-inactive analogues 25, 27, and 28 had fully extended side chains, with the carbohydrate moiety

  抗冻糖蛋白 (AFGP) 是一类独特的蛋白质，存在于居住在零度以下环境的许多生物体中，并通过防止体内冰生长来确保它们的生存。在过去的几年中，我们的实验室合成了功能性 C 连接的 AFGP 类似物（3 和 5），它们具有适合医疗、商业和工业应用的定制防冻活性。这些化合物是冰重结晶的有效抑制剂并且不表现出热滞后。目前的研究探讨了 5 中碳水化合物部分和多肽骨架之间含酰胺侧链长度的变化如何影响冰重结晶抑制 (IRI) 活性。类似物 5（n = 3，其中 n 是侧链中的碳数）是冰重结晶的有效抑制剂，而 4、6、和 7（分别为 n = 4、2 和 1）没有表现出 IRI 活性。使用圆二色性 (CD) 光谱检查 C 连接的 AFGP 类似物 4-7 中多肽骨架的溶液构象。结果表明，所有类似物在溶液中都表现出无规卷曲构象，并且用 5 观察到的 IRI 活性的急剧增加不是由于长程溶液构象的变化。对截断类似物
• Synthesis of a C-linked Antifreeze Glycoprotein (AFGP) Mimic:  Probes for Investigating the Mechanism of Action
  作者：Robert N. Ben、Adewale A. Eniade、Lisa Hauer

  DOI：10.1021/ol991025+

  日期：1999.12.1

  [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.