(S)-2',6'-二甲基酪氨酸盐酸盐 | 126312-63-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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: (S)-2',6'-二甲基酪氨酸盐酸盐
• 中文别名: (S)-2’,6’-二甲基酪氨酸盐酸盐
• 英文名称: 2',6'-dimethyl-L-tyrosine hydrochloride
• 英文别名: 2,6-dimethyl-(S)-tyrosine hydrochloride；(S)-2-Amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid hydrochloride；(2S)-2-amino-3-(4-hydroxy-2,6-dimethylphenyl)propanoic acid;hydrochloride
• CAS: 126312-63-8
• 化学式: C₁₁H₁₅NO₃*ClH
• 分子量: 245.706
• InChiKey: WEZPIGXFXWUCDS-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.75
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  (S)-2',6'-二甲基酪氨酸盐酸盐 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Structural studies of [2′,6′-dimethyl-l-tyrosine1]endomorphin-2 analogues: enhanced activity and cis orientation of the Dmt-Pro amide bond

  摘要：

  Analogues of endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) (1) were designed to examine the importance of each residue on mu-opioid receptor interaction. Replacement of Tyr(1) by 2',6'-dimethyl-L-tyrosine (Dmt) (9-12) exerted profound effects: [Dmt(1)]EM-2 (9) elevated mu-opioid affinity 4.6-fold (K(i)mu = 0.15 nM) yet selectivity fell 330-fold as delta-affinity rose (K(i)delta = 28.2 nM). This simultaneous increased mu- and delta-receptor bioactivities resulted in dual agonism (IC50 = 0.07 and 1.87 nM, respectively). While substitution of Phe(4) by a phenethyl group (4) decreased mu affinity (K(i)mu 13.3 nM), the same derivative containing Dmt (12) was comparable to EM-2 but also acquired weak delta antagonism (pA(2) = 7.05). H-1 NMR spectroscopy revealed a trans configuration (1:2 to 1:3, cis/trans) in the Tyr-Pro amide bond, but a cis configuration (5:3 to 13:7, cis/trans) with Dmt-Pro analogues. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00068-3
• 作为产物：
  描述：

  2',6'-二甲基-L-酪氨酸 在 盐酸 作用下， 以 水 为溶剂， 生成 (S)-2',6'-二甲基酪氨酸盐酸盐
  参考文献：
  名称：

  A highly efficient stereocontrolled synthesis of (S)-2′,6′-dimethyltyrosine [(S)-DMT]

  摘要：

  A new, practical and very convenient stereocontrolled synthesis of (S)-2',6'-dimethyltyrosine [(S)-Dmt] 4 was accomplished in a good yield, Starting from the chiral synthon 1.4-N,N-[(S)-phenylethyl]-piperazine-2,5-dione 1. The procedure, which is an extension Of our original strategy and occurs with a high level of stereoselectivity (>98%), is simple and inexpensive allowing LIS to prepare the unnatural alpha-aminoacid (S)-Dmt also on a multi-gram scale. (C) 2009 ElsevieF Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.06.004

文献信息

• N-Adamantane-substituted tetrapeptide amides
  申请人：G. D. Searle & Co.

  公开号：US04273704A1

  公开（公告）日：1981-06-16

  N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.

  本文披露了N-戊二醛基取代的四肽酰胺及其药理学上可接受的盐。这些化合物是镇痛肽恩啡啶的类似物，其中第5位的蛋氨酸或亮氨酸被戊二醛基酰胺取代，第2位的甘氨酸被各种氨基酸残基取代。可选地，第1位的酪氨酸和第4位的苯丙氨酸可以被各种氨基酸残基取代。这些化合物在阿片受体位点表现出激动剂活性，并可用作镇痛剂。
• Preparation of Constrained Unnatural Aromatic Amino Acids<i>via</i>Unsaturated Diketopiperazine Intermediate
  作者：Adriano Mollica、Roberto Costante、Sako Mirzaie、Simone Carradori、Giorgia Macedonio、Azzurra Stefanucci、Ettore Novellino

  DOI：10.1002/jhet.2489

  日期：2016.11

  Unnatural aromatic amino acids are useful tools in drug discovery, since their insertion in bioactive peptide sequences can change the side chains spatial orientation, the backbone conformation and above all, their bioactivity. In this communication, we propose a straightforward method to synthesize 2′,6′‐dimethyl‐tyrosine and 2′,6′‐dimehylphenyl‐alanine derivatives as handling building blocks for

  非天然芳族氨基酸是药物发现中的有用工具，因为它们插入生物活性肽序列中可以改变侧链的空间方向，主链构象以及最重要的是其生物活性。在本文中，我们提出了一种简单的方法来合成2'，6'-二甲基酪氨酸和2'，6'-二甲基苯基丙氨酸衍生物，作为通过不饱和二酮哌嗪（DKP）中间体进行肽合成的基础。
• Solid-Phase Azopeptide Diels–Alder Chemistry for Aza-pipecolyl Residue Synthesis To Study Peptide Conformation
  作者：Ramesh Chingle、Mukandila Mulumba、Nga N. Chung、Thi M.-D. Nguyen、Huy Ong、Steven Ballet、Peter W. Schiller、William D. Lubell

  DOI：10.1021/acs.joc.8b03283

  日期：2019.5.17

  Solid-phase chemistry for the synthesis and Diels–Alder reaction of Fmoc-protected azopeptides has been developed and used to construct aza-pipecolyl (azaPip) peptides. Considering their ability to induce electronic and structural constraints that favor cis-amide isomer geometry and type VI β-turn conformation in model peptides, azaPip residues have now been introduced into biologically relevant targets

  用于Fmoc保护的偶氮肽的合成和Diels-Alder反应的固相化学已得到开发，并用于构建氮杂-哌啶基（azaPip）肽。考虑到它们在模型肽中诱导有利于顺式酰胺异构体几何形状和VI型β-转角构象的电子和结构限制的能力，现在已经通过这种可行的合成方法将azaPip残基引入生物学相关的靶标中。通过使用azaPip残基研究阿片类药物的构象要求和分化的36种受体肽配体簇，证明了转角构象异构体对于受体亲和力，选择性和活性很重要。
• Convenient, asymmetric synthesis of enantiomerically pure 2′,6′-dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine
  作者：Xuejun Tang、Vadim A. Soloshonok、Victor J. Hruby

  DOI：10.1016/s0957-4166(00)00250-0

  日期：2000.7

  Asymmetric synthesis of (S)-2′,6′-dimethyltyrosine (DMT) via reactions of 4′-benzyloxy-2′,6′-dimethylbenzyl bromide with Ni(II)-complexes of the chiral Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone was developed. Inexpensive and readily available reagents and solvents involved, including recyclable chiral auxiliary, simplicity of the experimental procedures and high chemical

  通过4'-苄氧基-2'，6'-二甲基苄基溴与甘氨酸手性席夫碱的Ni（II）络合物与（S）的反应，不对称合成（S）-2'，6'-二甲基酪氨酸（DMT）） - ø - [ ñ - （ñ -benzylprolyl）氨基]苯甲酮被开发。所涉及的廉价且容易获得的试剂和溶剂，包括可回收的手性助剂，简单的实验程序和高化学产率，使得该方法对于以克为单位制备目标氨基酸具有合成吸引力。
• 一种2，6-二甲基酪氨酸酯的拆分方法及其应用
  申请人：浙江普洛家园药业有限公司

  公开号：CN110467539B

  公开（公告）日：2023-01-06

  本发明公开了一种2，6‑二甲基‑L‑酪氨酸的制备方法,该方法包括如下步骤：将消旋的2，6‑二甲基‑酪氨酸制酯，然后通过动态动力学拆分得到2，6‑二甲基‑L‑酪氨酸酯的复盐，再通过脱保护得到目标产物2，6‑二甲基‑L‑酪氨酸。本发明具有原料易得，操作方便，收率高等特点，具有良好的工业应用和经济价值。