[(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-[2-[4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butylamino]-2-oxoethyl]oxan-2-yl]methyl acetate | 1253421-66-7

• 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: [(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-[2-[4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butylamino]-2-oxoethyl]oxan-2-yl]methyl acetate
• CAS: 1253421-66-7
• 化学式: C₂₃H₃₂N₂O₁₃
• 分子量: 544.513
• InChiKey: YJQJOKNMHBHRPP-VLWQACTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  N2-((benzyloxy)carbonyl)-N6-(2-((2R,3S,4R,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)acetyl)-L-lysine 在 1,1-二氯甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 [(2R,3R,4R,5S,6R)-3,4,5-triacetyloxy-6-[2-[4-[(4S)-2,5-dioxo-1,3-oxazolidin-4-yl]butylamino]-2-oxoethyl]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  General Method for Purification of α-Amino acid-N-carboxyanhydrides Using Flash Chromatography

  摘要：

  We describe the application of flash column chromatography on silica gel as a rapid and general method to obtain pure a-amino acid-N-carboxyanhydride (NCA) monomers, the widely used precursors for the synthesis of polypeptides, without the need for recrystallization. This technique was effective at removing all common impurities from NCAs and was found to work for a variety of NCAs, including those synthesized using different routes, as well as those bearing either hydrophilic or hydrophobic side chains. All chromatographed NCAs required no further purification and could be used directly to form high molecular weight polypeptides. This procedure is especially useful for the preparation of highly functional and low melting NCAs that are difficult to crystallize and, consequently, to polymerize. This method solves many long-standing problems in NCA purification and provides rapid access to NCAs that were previously inaccessible in satisfactory quality for controlled polymerization. This method is also practical in that it requires less time than recrystallization and often gives NCAs in improved yields.

  DOI：

  10.1021/bm101123k

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。