L-aspartic acid γ-fluorenylmethyl ester hydrochloride | 122235-69-2

• 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: L-aspartic acid γ-fluorenylmethyl ester hydrochloride
• 英文别名: (2S)-2-amino-4-(9H-fluoren-9-ylmethoxy)-4-oxobutanoic acid;hydrochloride
• CAS: 122235-69-2
• 化学式: C₁₈H₁₇NO₄*ClH
• 分子量: 347.798
• InChiKey: DZXYQXXWJKPUOI-NTISSMGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  89.62
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile 、 L-aspartic acid γ-fluorenylmethyl ester hydrochloride 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以83%的产率得到BOC-L-天门冬氨酸Β-9-芴甲氧羰酰甲酯
  参考文献：
  名称：

  Convenient Syntheses of Fluorenylmethyl-Based Side Chain Derivatives of Glutamic and Aspartic acids, Lysine, and Cysteine

  摘要：

  报道了基于二甲基芴甲基的谷氨酸、天冬氨酸、赖氨酸和半胱氨酸侧链衍生物的高效实用的一锅法合成。同样，这些衍生物在固相肽合成中使用的溶剂和试剂中的稳定性/不稳定性也被讨论。

  DOI：

  10.1055/s-1990-26804
• 作为产物：
  描述：

  9-芴甲醇 在 盐酸 、 4-二甲氨基吡啶 、 氢溴酸 、 溶剂黄146 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 L-aspartic acid γ-fluorenylmethyl ester hydrochloride
  参考文献：
  名称：

  Potent and prolonged-acting cyclic lactam analogs of .alpha.-melanotropin: design based on molecular dynamics

  摘要：

  Utilizing results from previous structure-activity relationships and theoretical studies of alpha-melanotropin (alpha-MSH, Ac-Ser-Tyr-Ser-Met-Glu-His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2) and its related superpotent analogues, Ac-[Nle4,D-Phe7]-alpha-MSH and Ac-[Cys4,Cys10]-alpha-MSH, we have designed a new class of alpha-MSH4-13 and alpha-MSH4-10 cyclic lactam fragment analogues of alpha-melanotropin. The cyclic peptides have the following general structures: Ac-[Nle4,Xxx5,D-Phe7,Yyy10,Gly11]-alpha-MSH4-13- NH2 and Ac-[Nle4,Xxx5,D-Phe7,Yyy10]-alpha-MSH4-10-NH2, where Xxx = Glu or Asp and Yyy = Lys, Orn, Dab, or Dpr. Formation of the lactam bridge between the side-chain groups Xxx and Yyy was performed either in solution or on a solid-phase support. Seven cyclic peptides were prepared and bioassayed for their melanotropic potency by using standard frog (Rana pipiens) and lizard (Anolis carolinensis) skin bioassays. Relative to alpha-MSH (relative potency = 1), the potencies of the cyclic peptides in the lizard skin bioassay were as follows: alpha-MSH (1); Ac-[Nle4,Glu5,D-Phe7,Lys10,Gly11]-alpha-MSH4-13- NH2 (6); Ac-[Nle4,Asp5,D-Phe7,Lys10,Gly11]-alpha-MSH4-13- NH2 (100); Ac-[Nle4,Glu5,D-Phe7,Lys10]-alpha-MSH4-10-NH2 (9); Ac-[Nle4,Asp5,D-Phe7,Lys10]-alpha-MSH4-10-NH2 (90); Ac-[Nle4,Asp5,D-Phe7,Orn10]-alpha-MSH4-10-NH2 (20); Ac-[Nle4,Asp5,D-Phe7,Dab10]-alpha-MSH4-10-NH2 (5); Ac-[Nle4,Asp5,D-Phe7,Dpr10]-alpha-MSH4-10-NH2 (5). Similar results were obtained in the frog skin bioassay, but the analogues were much less potent. Cyclic melanotropins with 23-membered rings exhibited 100-fold higher melanotropic potency than alpha-MSH with selectivity for the lizard melanocyte receptors over the frog melanocyte receptors. Increasing or decreasing the ring size of these cyclic melanotropins from 23 diminishes the biological potency of the resulting cyclic peptide. The 23- and 24-membered ring analogues showed prolonged (residual) biological activities in both biological assays, but the smaller ring systems (20, 21, 22) did not. These results provide new insights into the structural and conformational requirements of alpha-MSH and its analogues at two different types of pigment cell (melanocyte) receptors.

  DOI：

  10.1021/jm00132a010

文献信息

• Solid-Phase Synthesis of Peptidyl Thioacids Employing a 9-Fluorenylmethyl Thioester-Based Linker in Conjunction with Boc Chemistry
  作者：David Crich、Kasinath Sana

  DOI：10.1021/jo901218g

  日期：2009.10.2

  A method for the synthesis of peptidyl thioacids is described on the basis of the use of the N-[9-(thiomethyl)-9H-fluoren-2-yl]succinamic acid and cross-linked aminomethyl polystyrene resin. The method employs standard Boc chemistry SPPS techniques in conjunction with 9-fluorenylmethyloxycarbonyl protection of side-chain alcohols and amines and 9-fluorenylmethyl protection of side-chain acids and thiols

  被使用的的基础上，描述了一种用于肽基硫代酸的合成方法Ñ [9-（甲硫基）-9 - ħ芴-2-基]琥珀酰胺酸和交联的氨基甲基聚苯乙烯树脂。该方法采用标准 Boc 化学 SPPS 技术，结合侧链醇和胺的 9-芴基甲氧羰基保护和侧链酸和硫醇的 9-芴甲基保护。从树脂上裂解是用哌啶完成的，哌啶也用于去除侧链保护并避免通常与 Boc 化学 SPPS 的树脂裂解阶段相关的 HF 条件。根据公认的方法，通过标准烷基化将如此获得的硫代酸以高产率转化为简单的硫代酯。
• AL-OBEIDI, FAHAD;SANDERSON, DOUGLAS G.;HRUBY, VICTOR J., INT. J. PEPTIDE AND PROTEIN RES., 35,(1990) N, C. 215-218
  作者：AL-OBEIDI, FAHAD、SANDERSON, DOUGLAS G.、HRUBY, VICTOR J.

  DOI：——

  日期：——