(2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]-ethanoic acid | 1015422-11-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]-ethanoic acid
• 英文别名: (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]oxan-2-yl]acetic acid
• CAS: 1015422-11-3
• 化学式: C₁₈H₃₂N₂O₁₀
• 分子量: 436.459
• InChiKey: RAHAMTCTYHPJMB-HKLHZYFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]-ethanoic acid 在 吡啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 N'-dodecyl-(2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(tert-butoxycarbonylamino-2,3,4-tri-O-phenylcarbamoyl)-β-D-glucopyranosyl]ethanamide
  参考文献：
  名称：

  Synthesis and antibacterial properties of carbohydrate-templated lysine surfactants

  摘要：

  The synthesis of four dicationic glucose-templated D-lysine-derived surfactants and their two unmodified D-lysine-analogs is described. Replacement of D-lysine by D-glucose-templated-D-lysine provides a general tool to introduce chemical diversity into the side chain of lysine. The presence of the polyfunctional D-gluco-configured polyol scaffold provides rich opportunities to study structure-activity relationships in lysine-lipid conjugates. All cationic lipids were tested for inhibition of bacterial growth using a panel of clinically relevant Gram-positive and Gram-negative strains. Our results show that substitution of D-lysine by D-glucose-templated D-lysine surfactants retains, but does not improve, the antibacterial activity. Similarly, conversion of the D-gluco-based polyol scaffold into a hydrophobically enhanced tri-O-phenylcarbamate scaffold does not further enhance the antibacterial activity of the cationic lipid. However, improvements in the antibacterial activity were observed by guanidinylation of the two lysine-based amino groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.01.025
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 palladium dihydroxide 、 palladium(II) hydroxide/carbon 吡啶 、 盐酸 、 lithium hydroxide 、 sodium azide 、 水 、 氢气 、 三正丁基氢锡 、 三乙胺 、 pyridinium chlorochromate 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、101.33 kPa 条件下， 反应 58.0h， 生成 (2R)-2-(t-butoxycarbonylamino)-2-[6-deoxy-6-(t-butoxycarbonylamino)-β-D-glucopyranosyl]-ethanoic acid
  参考文献：
  名称：

  Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same

  摘要：

  这项发明通常涉及四氢吡喃基衍生的氨基酸，它们的合成以及它们被纳入肽和肽类似物中。四氢吡喃基约束氨基酸的侧链，从而提供一种可能作为糖或氨基酸类似物的分子，同时也作为组合合成的支架。

  公开号：

  US20080275213A1

文献信息

• Synthesis of glucose-templated lysine analogs and incorporation into the antimicrobial dipeptide sequence kW-OBn
  作者：Kaidong Zhang、Dhananjoy Mondal、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.carres.2008.04.018

  日期：2008.7

  The synthesis of two glucose-templated (GlcT) lysine analogs GlcTK and GlcTk in which the side chain of D- and L-lysine (k and K) is conformationally constrained via incorporation into a D-glucose scaffold is described. A key-step in the synthesis is a high yielding, reductive ring opening of an exocyclic glucose-derived epoxide to form a alpha-hydroxy ester that can be converted into GlcTK and GlcTk

  描述了两个葡萄糖模板化的（GlcT）赖氨酸类似物GlcTK和GlcTk的合成，其中D-和L-赖氨酸（k和K）的侧链通过掺入D-葡萄糖支架而在构象上受到约束。合成中的关键步骤是高产量的环外葡萄糖衍生的环氧化物的还原环开环反应，以形成可转化为GlcTK和GlcTk的α-羟基酯。为了证明在肽合成中使用这些构件，我们在抗菌二肽序列kW-OBn（W = L-色氨酸）中替换了D-赖氨酸，并确定了对各种革兰氏阳性和革兰氏阴性生物的抗菌活性。我们的结果表明，二肽kW-OBn中未保护的GlcTk取代D-赖氨酸会导致抗菌活性降低。
• Synthesis of Carbohydrate-Templated Amino Acids and Methods of Using Same
  申请人：Schweizer Frank

  公开号：US20080275213A1

  公开（公告）日：2008-11-06

  The present invention generally relates to tetrahydropyranyl-derivatized amino acids, their syntheses and their incorporation into peptides and peptidomimetics. The tetrahydropyran moiety constrains the side chain of an amino acid, thereby providing a molecule that may act as a sugar- or amino acid-mimetic as well as a scaffold for combinatorial synthesis.

  这项发明通常涉及四氢吡喃基衍生的氨基酸，它们的合成以及它们被纳入肽和肽类似物中。四氢吡喃基约束氨基酸的侧链，从而提供一种可能作为糖或氨基酸类似物的分子，同时也作为组合合成的支架。
• Synthesis and antibacterial properties of carbohydrate-templated lysine surfactants
  作者：Dhananjoy Mondal、George G. Zhanel、Frank Schweizer

  DOI：10.1016/j.carres.2011.01.025

  日期：2011.4

  The synthesis of four dicationic glucose-templated D-lysine-derived surfactants and their two unmodified D-lysine-analogs is described. Replacement of D-lysine by D-glucose-templated-D-lysine provides a general tool to introduce chemical diversity into the side chain of lysine. The presence of the polyfunctional D-gluco-configured polyol scaffold provides rich opportunities to study structure-activity relationships in lysine-lipid conjugates. All cationic lipids were tested for inhibition of bacterial growth using a panel of clinically relevant Gram-positive and Gram-negative strains. Our results show that substitution of D-lysine by D-glucose-templated D-lysine surfactants retains, but does not improve, the antibacterial activity. Similarly, conversion of the D-gluco-based polyol scaffold into a hydrophobically enhanced tri-O-phenylcarbamate scaffold does not further enhance the antibacterial activity of the cationic lipid. However, improvements in the antibacterial activity were observed by guanidinylation of the two lysine-based amino groups. (C) 2011 Elsevier Ltd. All rights reserved.