(E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid | 196097-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid
• 英文别名: 3-[2-[2-[2-[(E)-4-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]oxybut-2-enoxy]ethoxy]ethoxy]ethoxy]propanoic acid
• CAS: 196097-59-3
• 化学式: C₃₁H₃₉NO₁₀
• 分子量: 585.651
• InChiKey: CPLZGVXIMQZEEM-YQTDCCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  42
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid 在 N-羟基丁二酰亚胺 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 反应 19.92h， 生成 (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoyl-β-alanine
  参考文献：
  名称：

  HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides

  摘要：

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.

  DOI：

  10.1021/jo960743w
• 作为产物：
  描述：

  (E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester 在 四丁基溴化铵 、 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 (E)-17-[N-(9-fluorenylmethoxycarbonyl)-L-alanyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid
  参考文献：
  名称：

  HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides

  摘要：

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.

  DOI：

  10.1021/jo960743w

文献信息

• Chemoenzymatic Solution- and Solid-Phase Synthesis of <i>O</i>-Glycopeptides of the Mucin Domain of MAdCAM-1. A General Route to <i>O</i>-LacNAc, <i>O</i>-Sialyl-LacNAc, and <i>O</i>-Sialyl-Lewis-X Peptides
  作者：Oliver Seitz、Chi-Huey Wong

  DOI：10.1021/ja971383c

  日期：1997.9.1

  Glycosyltransferases were employed to extend the glycan on supported and unsupported O-GlcNAc-octapeptide substrates. The acid- and base-sensitive O-glycopeptides were released under practically neutral conditions, taking advantage of the palladium(0)-catalyzed cleavage of the allylic linkage. Studies toward the selective O-deacetylation of ester-linked glycopeptides possessing O-acetyl-pr...

  描述了一种用于固相合成含有 O 连接唾液酸-刘易斯-X (SLex) 四糖的糖肽的有效和通用方法。使用组合化学酶法，首次合成了非天然 β-O 连接的 SLex，该 SLex 连接到 L-选择素配体 MAdCAM-1 的粘蛋白结构域的部分序列。树脂结合的 O-糖缀合物由新的 Fmoc-苏氨酸结构单元合成，该结构单元带有 O-未保护的 β-连接的 N-乙酰葡萄糖胺 (GlcNAc) 部分。酸和碱稳定的 HYCRON 接头能够完全去除固相上的所有保护基团。糖基转移酶用于在支持和未支持的 O-GlcNAc-八肽底物上扩展聚糖。酸和碱敏感的 O-糖肽在几乎中性的条件下释放，利用钯（0）催化的烯丙基键断裂。具有O-乙酰基-pr的酯连接糖肽的选择性O-脱乙酰化研究
• HYCRON, an Allylic Anchor for High-Efficiency Solid Phase Synthesis of Protected Peptides and Glycopeptides
  作者：Oliver Seitz、Horst Kunz

  DOI：10.1021/jo960743w

  日期：1997.2.1

  The recently developed allylic HYCRON anchor(1) exhibits excellent properties for the solid phase synthesis of protected peptides and glycopeptides. Model reactions with analogous low molecular weight compounds assessed the acid- and base-stability of the polar and flexible HYCRON linkage. The new anchor is available in a two-step synthesis and allows the use of both the Boc- and the Fmoc-strategy, which can even be combined within one synthesis. Protected glycopeptides are released under almost neutral conditions, taking advantage of the Pd(O)-catalyzed allyl transfer to a weakly basic nucleophile such as N-methylaniline. The highly efficient synthesis of O-alpha GalNAc-(T-N)-peptides of the MUC-1 repeating unit is described. Acid- and base-stability of the allyl ester linkage enabled the synthesis of an O-glucosylated peptide by first removing a threonine tert-butyl group on the solid phase and subsequently glycosylating the liberated resin-bound hydroxyl component.