Fmoc-D-丙氨酸醇 | 202751-95-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 氨基醇类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: Fmoc-D-丙氨酸醇
• 中文别名: N-[(1R)-2-羟基-1-甲基乙基]-氨基甲酸9H-芴-9-基甲酯；FMOC-D-丙氨酸醇；(R)-(1-羟基丙烷-2-基)氨基甲酸酯(9H-芴-9-基)甲基；Fmoc-d-丙氨醇；FMOC-D-丙氨醇；(R)-(9H-芴-9-基)甲基(1-羟基丙-2-基)氨基甲酸酯；FMOC-D-丙氨酸-OL；Fmoc-d-丙氨酸醇；(R)-(9H-氟-9-基)甲基(1-羟基丙-2-基)氨基甲酸酯
• 英文名称: (R)-(9H-fluoren-9-yl)methyl 1-hydroxypropan-2-ylcarbamate
• 英文别名: Fmoc-D-alaninol；Fmoc-D-Alaol；9H-fluoren-9-ylmethyl N-[(2R)-1-hydroxypropan-2-yl]carbamate
• CAS: 202751-95-9
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: GIZCEJUGNDJXMH-GFCCVEGCSA-N

物化性质

• 熔点：
  148-151 °C
• 沸点：
  503.9±33.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

反应信息

• 作为反应物：
  描述：

  Fmoc-D-丙氨酸醇 生成 Fmoc-D-丙氨醛
  参考文献：
  名称：

  [EN] LEFT-HANDED GAMMA-PEPTIDE NUCLEIC ACIDS, METHODS OF SYNTHESIS AND USES THEREFOR
  [FR] ACIDES NUCLÉIQUES GAMMA-PEPTIDIQUES À HÉLICE À PAS DE ROTATION À GAUCHE, LEURS PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS

  摘要：

  提供了制备手性γΡΝΑ（伽马肽核酸）单体的光学纯制备方法。提供了包含手性γΡΝΑ结构的纳米结构。提供了扩增和检测特定核酸的方法，包括原位方法，以及在这些方法中有用的组合物和试剂盒。最后，提供了从右旋螺旋PNA，核酸和核酸类似物结构转化为左旋γΡΝΑ的核碱基序列的方法，反之亦然。

  公开号：

  WO2015172058A1
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 以1.32 g的产率得到Fmoc-D-丙氨酸醇
  参考文献：
  名称：

  Structure−Affinity Relationships of Glutamine Mimics Incorporated into Phosphopeptides Targeted to the SH2 Domain of Signal Transducer and Activator of Transcription 3

  摘要：

  In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gin mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4-methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date.

  DOI：

  10.1021/jm901105k

文献信息

• An expedient route for the reduction of carboxylic acids to alcohols employing 1-propanephosphonic acid cyclic anhydride as acid activator
  作者：G. Nagendra、C. Madhu、T.M. Vishwanatha、Vommina V. Sureshbabu

  DOI：10.1016/j.tetlet.2012.06.108

  日期：2012.9

  method for the synthesis of alcohols from the corresponding carboxylic acids is described. Activation of carboxylic acid with 1-propanephosphonic acid cyclic anhydride (T3P) and subsequent reduction using NaBH4 yield the alcohol in excellent yields with good purity. Reduction of several alkyl/aryl carboxylic acids and Nα-protected amino acids/peptide acids as well as Nβ-protected amino acids was successfully

  描述了一种由相应的羧酸合成醇的简单有效的方法。用1-丙烷膦酸环酐（T3P）活化羧酸，然后使用NaBH 4还原，可得到纯度高，纯度高的醇。的减少几个烷基/芳基羧酸和N α -保护的氨基酸/肽酸以及如N β -保护的氨基酸被成功地执行，以获得良好的收率相应的醇。所有产物均通过1 H NMR和质谱分析充分表征。该过程温和，简单，并且容易分离产物。
• A facile synthesis and crystallographic analysis of N-protected β-amino alcohols and short peptaibols
  作者：Sandip V. Jadhav、Anupam Bandyopadhyay、Sushil N. Benke、Sachitanand M. Mali、Hosahudya N. Gopi

  DOI：10.1039/c0ob01226b

  日期：——

  for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals

  一种简便，高效且无外消旋的方法，使用该方法合成N保护的β-氨基醇和肽醇N-羟基琥珀酰亚胺描述了活性酯。使用这种方法，可以高产率分离出二肽，三肽和五肽醇。分析了β-氨基醇，二肽和三肽醇的晶体构象，在三肽醇晶体中观察到了明确定义的III型β角。发现该方法与Fmoc-，Boc-和其他侧链保护基相容。
• [EN] LEFT-HANDED GAMMA-PEPTIDE NUCLEIC ACIDS, METHODS OF SYNTHESIS AND USES THEREFOR<br/>[FR] ACIDES NUCLÉIQUES GAMMA-PEPTIDIQUES À HÉLICE À PAS DE ROTATION À GAUCHE, LEURS PROCÉDÉS DE SYNTHÈSE ET UTILISATIONS
  申请人：UNIV CARNEGIE MELLON

  公开号：WO2015172058A1

  公开（公告）日：2015-11-12

  A method of making optically pure preparations of chiral γΡΝΑ (gamma peptide nucleic acid) monomers is provided. Nanostructures comprising chiral γΡΝΑ structures also are provided. Methods of amplifying and detecting specific nucleic acids, including in situ methods are provided as well as compositions and kits useful in those methods. Lastly, methods of converting nucleobase sequences from right-handed helical PNA, nucleic acid and nucleic acid analog structures to left-handed γΡΝΑ, and vice- versa, are provided.

  提供了制备手性γΡΝΑ（伽马肽核酸）单体的光学纯制备方法。提供了包含手性γΡΝΑ结构的纳米结构。提供了扩增和检测特定核酸的方法，包括原位方法，以及在这些方法中有用的组合物和试剂盒。最后，提供了从右旋螺旋PNA，核酸和核酸类似物结构转化为左旋γΡΝΑ的核碱基序列的方法，反之亦然。
• US8019550B2
  申请人：——

  公开号：US8019550B2

  公开（公告）日：2011-09-13
• Structure−Affinity Relationships of Glutamine Mimics Incorporated into Phosphopeptides Targeted to the SH2 Domain of Signal Transducer and Activator of Transcription 3
  作者：Pijus K. Mandal、Zhiyong Ren、Xiaomin Chen、Chiyi Xiong、John S. McMurray

  DOI：10.1021/jm901105k

  日期：2009.10.8

  In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gin mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4-methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date.