Fmoc-D-丙氨醛 | 127043-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-D-丙氨醛
• 英文名称: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-alaninal
• 英文别名: Fmoc-D-ala-aldehyde；9H-fluoren-9-ylmethyl N-[(2R)-1-oxopropan-2-yl]carbamate
• CAS: 127043-32-7
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: LJGFXAKKZLFEDR-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Fmoc-D-丙氨醛 在 sodium cyanoborohydride 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 {[(R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-propyl]-[2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid benzyl ester
  参考文献：
  名称：

  Synthesis of chiral peptide nucleic acids using Fmoc chemistry

  摘要：

  A Fmoc-based synthesis of chiral PNAs is described. Chiral monomer backbones were efficiently prepared by reductive amination of N-Fmoc-protected L,D-alaninals with glycine esters and the subsequent acylation of free amines with thymine-1-ylacetic acid. The dimer derivative of L-amino acid was prepared in solution. Finally, a chiral decamer was obtained by a solid phase strategy using a succinyl-linked support. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00789-x
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Fmoc-D-丙氨醛
  参考文献：
  名称：

  Synthesis of chiral peptide nucleic acids using Fmoc chemistry

  摘要：

  A Fmoc-based synthesis of chiral PNAs is described. Chiral monomer backbones were efficiently prepared by reductive amination of N-Fmoc-protected L,D-alaninals with glycine esters and the subsequent acylation of free amines with thymine-1-ylacetic acid. The dimer derivative of L-amino acid was prepared in solution. Finally, a chiral decamer was obtained by a solid phase strategy using a succinyl-linked support. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00789-x

文献信息

• Helical Oligomers of Thiazole-Based γ-Amino Acids: Synthesis and Structural Studies
  作者：Loïc Mathieu、Baptiste Legrand、Cheng Deng、Lubomir Vezenkov、Emmanuel Wenger、Claude Didierjean、Muriel Amblard、Marie-Christine Averlant-Petit、Nicolas Masurier、Vincent Lisowski、Jean Martinez、Ludovic T. Maillard

  DOI：10.1002/anie.201302106

  日期：2013.6.3

  9‐Helix: 4‐Amino(methyl)‐1,3‐thiazole‐5‐carboxylic acids (ATCs) were synthesized as new γ‐amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X‐ray crystallography. The ATC sequences adopted a well‐defined 9‐helix structure in the solid state and in aprotic and protic organic solvents as well as in aqueous

  9-螺旋：合成了4-氨基（甲基）-1,3-噻唑-5-羧酸（ATC）作为新的γ-氨基酸构件。各种ATC低聚物的结构在溶液中通过CD和NMR光谱分析，在固态下通过X射线晶体学分析。ATC序列在固态，非质子和质子有机溶剂以及水溶液中均采用明确定义的9螺旋结构。
• INDOLE, INDAZOLE, AND BENZAZOLE DERIVATIVE
  申请人：Sumitomo Pharmaceuticals Company, Limited

  公开号：EP1514869A1

  公开（公告）日：2005-03-16

  The compound of the formula (I): wherein W is a group of the following formula (VIII) binding to any possible position on the Q: Q is, together with W, a group of the formula: -C(M=C(R3A)-N(R3)-, etc.; R3A is H or optionally substituted lower alkyl; R4, R5, R6, and R7 are independently H or optionally substituted lower alkyl; R1 is optionally substituted lower alkyl, etc.; R2 is H, etc.; R3 is H, etc.; Ar is phenyl, etc., or a pharmaceutically acceptable salt thereof, where these compounds exhibiting β3-adrenoceptor-stimulating activity and being useful as a medicament for treatment of obesity, etc.

  公式(I)的化合物： 其中W是以下公式(VIII)的基团，可以与Q的任何可能位置结合： Q与W一起是以下公式的基团：-C(M=C(R3A)-N(R3)-等； R3A是H或可选地取代的低级烷基；R4、R5、R6和R7独立的是H或可选地取代的低级烷基；R1是可选地取代的低级烷基等；R2是H等；R3是H等；Ar是苯基等，或其药物可接受的盐，其中这些化合物具有β3-肾上腺素受体刺激活性，并作为治疗肥胖等的药物有用。
• Synthesis of chiral N-protected α-amino aldehydes by reduction of N-protected N-carboxyanhydrides (UNCAs)
  作者：Jean-Alain Fehrentz、Catherine Pothion、Jean-Christophe Califano、Albert Loffet、Jean Martinez

  DOI：10.1016/0040-4039(94)88419-6

  日期：1994.11

  A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) α-amino aldehydes under mild conditions is described. Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Boc, Fmoc)-N-carboxyanhydrides (UNCAs) with equivalent amounts of lithium tris(tertbutoxy)aluminium hydride [LiAlH(O-t-Bu)3] or lithium tris[(3-ethyl-3-pentyl)oxy]aluminium

  描述了在温和条件下容易地一步合成多种N-保护的（Boc，Z，Fmoc）α-氨基醛的方法。通过用等量的三（叔丁氧基）锂铝还原N-保护的（Z，Boc，Fmoc）-N-羧基酸酐（UNCA），可以高收率获得纯N-保护的（Boc，Z，Fmoc）α-氨基醛。氢化物[LiAlH（Ot-Bu）3 ]或氢化三[（3-乙基-3-戊基）氧基]氢化铝锂（LTEPA）作为溶剂。该反应简单，快速并且进行时没有可检测的外消旋作用。
• A Facile One-pot Synthesis of N α-Urethane Protected 3-Amino Alkyl Isoxazole-5-Carboxylic Acids and their Utility for the Preparation of Isoxazole-Linked Peptidomimetics
  作者：G. Chennakrishnareddy、B. Vasantha、N. Narendra、Vommina V. Sureshbabu

  DOI：10.1007/s10989-011-9256-x

  日期：2011.9

  Cu(I) catalyzed [3+2] cycloaddition of in situ generated N α-Fmoc/Boc/Z-protected amino alkyl nitrile oxide with propiolic acid has led to a new class of 3,5-disubstituted isoxazole-bearing amino acid derivatives. The click chemistry protocol described herein is efficient in furnishing the isoxazole embedded amino acids. These unnatural synthons were subjected to chain extension on N- as well as C-termini

  的Cu（I）催化的[3 + 2]的在原位产生环加成Ñ α -Fmoc /的Boc / Z保护的氨基酸与丙炔酸已经导致了一类新的3,5-二取代的异恶唑轴承氨基酸衍生物烷基氧化腈。本文所述的点击化学方案可有效提供异恶唑嵌入的氨基酸。这些非天然的合成子在N-和C-末端上进行链延伸，以获得带有3，5-二取代的异恶唑的二和三肽类似物。
• Rational Design and Synthesis of Right-Handed <scp>d</scp>-Sulfono-γ-AApeptide Helical Foldamers as Potent Inhibitors of Protein–Protein Interactions
  作者：Peng Sang、Yan Shi、Pirada Higbee、Minghui Wang、Sami Abdulkadir、Junhao Lu、Gary Daughdrill、Jiandong Chen、Jianfeng Cai

  DOI：10.1021/acs.joc.0c00996

  日期：2020.8.21

  right-handed d-sulfono-γ-AApeptides reveal much-enhanced binding affinity compared to the p53 peptide. The design of d-sulfono-γ-AApeptides may provide a new and alternative strategy to modulate protein–protein interactions.

  已经有效地设计和合成了前所未有的新型螺旋折叠器。均质右旋d-磺基-γ-AApeptides代表了新一代非天然螺旋肽模拟物，其具有与α-肽相似的折叠构象，使其成为设计α-螺旋模拟物的理想分子支架。正如 p53-MDM2 PPI 作为模型应用所证明的那样，与 p53 肽相比，右手d-磺基-γ-AApeptides 显示出大大增强的结合亲和力。d-磺基-γ-AApeptides的设计可能为调节蛋白质-蛋白质相互作用提供一种新的替代策略。