2,4,6-三甲基-D-苯丙氨酸 | 146277-48-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苯丙氨酸类衍生物
• 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
• 中文名称: 2,4,6-三甲基-D-苯丙氨酸
• 中文别名: D-2,4,6-三氟-Phe-OH
• 英文名称: (2R)-mesitylalanine
• 英文别名: (2R)-2-azaniumyl-3-(2,4,6-trimethylphenyl)propanoate
• CAS: 146277-48-7
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: CRNOZLNQYAUXRK-LLVKDONJSA-N

物化性质

• 沸点：
  357.2±30.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基-D-苯丙氨酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 生成 N-Fmoc-D-mesitylalanine
  参考文献：
  名称：

  A unified approach to mesityl amino acids based on Sharpless dihydroxylation

  摘要：

  Enantioselective syntheses of two mesityl (2,4,6-trimethylphenyl) amino acids are described. Starting from ethyl 3-mesityl-2-propenoate both enantiomeric dihydroxy esters 5 were prepared in excellent yield and enantiomeric purity (>99% ee) by Sharpless dihydroxylation. Each diol was converted into ethyl 3-azido-2-hydroxy-3-mesitylpropanoate 3 which is the common intermediate. Compound (2S,3S)-3 was transformed into Fmoc-D-mesitylglycine D-1 and Fmoc-L-mesitylalanine L-2 through two four-step-sequences. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.041
• 作为产物：
  描述：

  (2R)-mesitylalanine ethyl ester 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 生成 2,4,6-三甲基-D-苯丙氨酸
  参考文献：
  名称：

  A unified approach to mesityl amino acids based on Sharpless dihydroxylation

  摘要：

  Enantioselective syntheses of two mesityl (2,4,6-trimethylphenyl) amino acids are described. Starting from ethyl 3-mesityl-2-propenoate both enantiomeric dihydroxy esters 5 were prepared in excellent yield and enantiomeric purity (>99% ee) by Sharpless dihydroxylation. Each diol was converted into ethyl 3-azido-2-hydroxy-3-mesitylpropanoate 3 which is the common intermediate. Compound (2S,3S)-3 was transformed into Fmoc-D-mesitylglycine D-1 and Fmoc-L-mesitylalanine L-2 through two four-step-sequences. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.041

文献信息

• SSTR1-selective analogs
  申请人：——

  公开号：US20020173618A1

  公开（公告）日：2002-11-21

  Analogs of SRIF which are selective for SSTR1 in contrast to the other cloned SRIF receptors. These analogs are useful in determining the tissue and cellular expression of the receptor SSTR1 and its biological role in the endocrine, exocrine and nervous system, as well as in regulating tumor growth. SRIF analog peptides, such as des-AA 1,2,5 [D-Trp 8 , NMeIAmp 9 , Tyr 11 ]-SRIF and counterparts incorporating Cbm at the N-terminus and/or N &agr; Ser 13 , inhibit the binding of a universal SRIF radioligand to the cloned human receptor SSTR1, but they do not bind with significant affinity to human SSTR2, SSTR3, SSTR4 or SSTR5. By incorporating an iodinated tyrosine in position-2 or in position-11 in these SSTR1-selective SRIF analogs, a labeled compound useful in drug-screening methods is provided. The N-terminus accommodates bulky moieties without loss of selectivity, and a carbamoyl moiety or a conjugating agent that will accept a radioactive nuclide or will link to a cytotoxin may be present at the N-terminus.

  与其他克隆的 SRIF 受体相比，SRIF 的类似物对 SSTR1 具有选择性。这些类似物有助于确定 SSTR1 受体在组织和细胞中的表达，及其在内分泌、外分泌和神经系统中的生物学作用，以及在调节肿瘤生长方面的作用。SRIF 类似肽，如 des-AA 1,2,5 [D-Trp 8 、NMeIAmp 9 Tyr 11 ]-SRIF 以及在 N 端含有 Cbm 和/或 N &agr； Ser 13 抑制通用 SRIF 放射性配体与克隆人受体 SSTR1 的结合，但它们与人 SSTR2、SSTR3、SSTR4 或 SSTR5 的结合亲和力不强。通过在这些 SSTR1 选择性 SRIF 类似物的第 2 位或第 11 位加入一个碘化酪氨酸，提供了一种可用于药物筛选方法的标记化合物。N 端可容纳体积较大的分子而不会丧失选择性，N 端还可含有氨基甲酰基或可接受放射性核素或与细胞毒素连接的连接剂。
• US4740500A
  申请人：——

  公开号：US4740500A

  公开（公告）日：1988-04-26
• US5750499A
  申请人：——

  公开号：US5750499A

  公开（公告）日：1998-05-12
• US7019109B2
  申请人：——

  公开号：US7019109B2

  公开（公告）日：2006-03-28
• A unified approach to mesityl amino acids based on Sharpless dihydroxylation
  作者：Rosario Ramón、Mònica Alonso、Antoni Riera

  DOI：10.1016/j.tetasy.2007.10.041

  日期：2007.11

  Enantioselective syntheses of two mesityl (2,4,6-trimethylphenyl) amino acids are described. Starting from ethyl 3-mesityl-2-propenoate both enantiomeric dihydroxy esters 5 were prepared in excellent yield and enantiomeric purity (>99% ee) by Sharpless dihydroxylation. Each diol was converted into ethyl 3-azido-2-hydroxy-3-mesitylpropanoate 3 which is the common intermediate. Compound (2S,3S)-3 was transformed into Fmoc-D-mesitylglycine D-1 and Fmoc-L-mesitylalanine L-2 through two four-step-sequences. (c) 2007 Elsevier Ltd. All rights reserved.