L-蛋氨酸,N-[(2-羟基苯基)甲基]- | 154703-02-3

• 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: L-蛋氨酸,N-[(2-羟基苯基)甲基]-
• 英文名称: (S)-2-(2-hydroxybenzylamino)-4-(methylthio)butanoic acid
• 英文别名: 2-(2-hydroxybenzylamino)-4-(methylthio)butanoic acid；N-(2-hydroxybenzyl)-L-methionine；H2Smet；(2S)-2-[(2-hydroxyphenyl)methylamino]-4-methylsulfanylbutanoic acid
• CAS: 154703-02-3
• 化学式: C₁₂H₁₇NO₃S
• 分子量: 255.338
• InChiKey: WGJWHKHJFLIAEM-JTQLQIEISA-N

物化性质

• 熔点：
  227-229 °C
• 沸点：
  463.2±45.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  L-蛋氨酸,N-[(2-羟基苯基)甲基]- 、 苯硼酸 在 二甲基亚砜 作用下， 以 苯 为溶剂， 以76%的产率得到(2S,5S,6R)-2-phenyl-6-aza-1,3-dioxa-5-(2-methylsulfanyl-ethyl)-2-borabenzocyclononen-4-one
  参考文献：
  名称：

  X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones

  摘要：

  Nine new monomeric boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-ones (3a-3i) were prepared from N-(2-hydroxybenzyl)-alpha-aminoacids 1a-1i and phenylboronic acid 2 using 20:1 benzene-DMSO mixtures. The compounds were characterized by H-1-, C-13-, B-11-, N-15- and 2D-NMR (HETCOR, NOESY and COLOC) experiments, FT infrared, mass spectra and elemental analysis. Suitable monocrystals of cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3a), (2S,5S,6R)-2-phenyl-6-aza- 1,3-dioxa-5-sec butyl-2-borabenzocyclononen-4-one (3c) and 2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3h) were obtained and their structures are discussed. The X-ray structures, as well as the NMR data established that the configurations at the nitrogen and boron atoms are 'R' and 'S', respectively and the transannular fusion is cis. A semi-empirical (SAMI) study allowed calculation of the energy for all possible stereoisomers, showing that the stabilization increases as the THC (TetraHedral Character of the boron atom) increases and also as the N --> B bond distance decreases, in agreement with the experimental results. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01418-3
• 作为产物：
  描述：

  N-salicylidene-L-methionine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 生成 L-蛋氨酸,N-[(2-羟基苯基)甲基]-
  参考文献：
  名称：

  基于L-蛋氨酸的酚类化合物可介导异常的AgNP组装并发挥有效的抗生物膜作用†

  摘要：

  2-（2-羟基苄基氨基）-4-（甲硫基）丁酸（L）与加帽分子一起产生具有异常纳米结构的AgNP，这些纳米结构显示出对生物膜生长的有效抑制。AgNPs的纳米板会在L –PSS–AgNPs中自组装成微米大小的花瓣状结构，而L –SDS–AgNPs中的较小纳米板会形成具有可见空隙的介晶。L –PVA–和L –PVP–AgNPs显示出多分散的多形纳米颗粒，包括纳米棱镜，球体和平板。结构性质研究表明，Ag +离子的缓慢还原和L的亲硫相互作用是造成AgNPs异常形态和组织的原因。重要的L封端分子AgNPs对四种不同的细菌，金黄色葡萄球菌，铜绿假单胞菌，枯草芽孢杆菌和大肠杆菌均表现出强大的生物膜抑制作用，其中前两种是烧伤创面中的经典定植菌。BIC（生物膜抑制浓度）和MIC（最小抑制浓度）研究进一步证实了AgNPs的真正抗生物膜作用。揭示作用机理的研究表明，增强的抗生物膜作用可能归因于L引起的膜通透性和完

  DOI：

  10.1039/c6ra06806e

文献信息

• The role of a weakly coordinating thioether group in ligation controlled molecular self-assemblies and their inter-conversions in Ni(<scp>ii</scp>) complexes of <scp>l</scp>-methionine derived ligand
  作者：Rakesh Kumar、Vishal Mutreja、Gyaneshwar Sharma、Sanjeev Kumar、Anzar Ali、S. K. Mehta、P. Venugopalan、Ramesh Kataria、Subash Chandra Sahoo

  DOI：10.1039/c9nj02573a

  日期：——

  A series of Ni(II) complexes of an L-methionine derived reduced Schiff base ligand has been synthesized and their interconversions are investigated for the first time with the help of a variety of physico-chemical techniques. The different reactant/reagent conditions lead to mono- (1), di- (2a/2b) and tri-nuclear (3a/3b) Ni(II) complexes and they are unequivocally characterized by single crystal X-ray

  合成了一系列由L-蛋氨酸衍生的还原席夫碱配体的Ni（II）配合物，并借助多种物理化学技术首次研究了它们的相互转化。不同的反应物/试剂条件导致形成单（1），双（2a / 2b）和三核（3a / 3b）Ni（II）配合物，并且它们通过单晶X射线晶体学明确表征。碱离子K + / Na +可以用作将1转化为三核络合物3a /的有效模板3b在70℃升高的温度下是热稳定的，但是在存在强烈相互作用的18-冠-6-醚的情况下易于离解为1。2a在DMF中转化为2b，其中基本的结构变化是将一个DMF分子结合到Ni（II）中心之一的配位域中，同时释放了配体的配位硫醚臂。2a和2b也可以转换为自组装复合体（3a / 3b），然后在环境温度下加入碱金属盐。将溶液加热至70°C会使三核配合物分解，并出现明显的颜色变化，并且该循环可以重复几次。通过ESI质谱和紫外可见光谱清楚地确定了所有复杂物质在溶液中相互转化和保留的
• Effect of ligand and bridge substitution on chiral recognition of 1-phenylethylammonium cation by an anionic binuclear Ni(II) complex
  作者：Chandani Rani Das、Tanmay Dutta、Manabendra Ray

  DOI：10.1016/j.ica.2018.10.065

  日期：2019.2

  Abstract Chiral recognition is an important phenomenon. Identifying factors those influences recognition and resolution have significance in multiple areas. Earlier, we had reported recognition and resolution (30% ee) of 1-phenylethylammonium cation using an anionic binuclear Ni(II) complex of a l -histidine derived ligand. We have now synthesized its l -methionine analogue and also substituted the

  摘要手性识别是一个重要现象。识别那些影响识别和解决的因素在多个领域都具有重要意义。此前，我们已经报道了使用α-组氨酸衍生的配体的阴离子双核Ni（II）络合物识别并拆分1-苯基乙基铵阳离子（30％ee）。现在，我们已经合成了其1-甲硫氨酸类似物，并且还将桥接的乙酸盐替换为苯甲酸盐。氨基酸被取代，随后与外消旋的1-苯乙胺反应，导致分离出两种可能的非对映异构体（1和2）的团聚体晶体。这与显示假外消旋物形成的1-组氨酸类似物不同。大部分晶体的HPLC实验显示ee为30％。另一方面，氨基酸和桥连配体的取代导致单个非对映异构体（3）晶体的分离。大部分晶体的HPLC实验显示，ee改善了58％。因此，氨基酸的变化改变了晶体形成的机理，而没有改善对映体过量（ee），但是桥的变化几乎使％ee增加了一倍。为了理解原因，对复合物1-3进行了结构表征，并与先前报道的1-组氨酸类似物进行了比较。比较表明，在本系统中不
• Chantegrel, Bernard; Deshayes, Christian; Faure, Rene, Heterocycles, 1993, vol. 36, # 12, p. 2811 - 2818
  作者：Chantegrel, Bernard、Deshayes, Christian、Faure, Rene

  DOI：——

  日期：——
• Hydrogen-bonded copper(II) and nickel(II) complexes and coordination polymeric structures containing reduced Schiff base ligands
  作者：Bellam Sreenivasulu、Jagadese J. Vittal

  DOI：10.1016/j.ica.2008.12.018

  日期：2009.6

  Complexes [Cu(HSas)(H2O)] center dot 2H(2)O (H(3)Sas = N-(2-hydroxybenzyl)-L-aspartic acid) (1), [Cu(HMeSglu) (H2O)] center dot 2H(2)O (H(3)MeSglu = (N-(2-hydroxy-5-methylbenzyl)-L-glutamic acid) (2), [Cu-2(Smet)(2)] (H(2)Smet = (N-(2-hydroxybenzyl)-L-methionine) (3), [Ni(HSas)(H2O)] (4), [Ni-2(Smet) (H2O)(2)] (5), and [Ni(HSapg)(2)] (H(2)Sapg = (N-(2-hydroxybenzyl)-L-aspargine) (6) have been synthesized and characterized by chemical and spectroscopic methods. Structural determination by single crystal X-ray diffraction studies revealed 1D coordination polymeric structures in 2 and 4, and hydrogen-bonded network structure in 5 and 6. In contrast to previously reported coordination compounds with similar ligands, the phenol remains protonated and bonded to the metal ions in 2 and 4, and also probably in 1. However, the phenolic group is non-bonded in 6. (C) 2009 Elsevier B.V. All rights reserved.
• X-ray analysis and structural characterization of 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononenones
  作者：Hiram I Beltrán、Luis S Zamudio-Rivera、Teresa Mancilla、Rosa Santillan、Norberto Farfán

  DOI：10.1016/s0022-328x(02)01418-3

  日期：2002.9

  Nine new monomeric boronates of the type 2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-ones (3a-3i) were prepared from N-(2-hydroxybenzyl)-alpha-aminoacids 1a-1i and phenylboronic acid 2 using 20:1 benzene-DMSO mixtures. The compounds were characterized by H-1-, C-13-, B-11-, N-15- and 2D-NMR (HETCOR, NOESY and COLOC) experiments, FT infrared, mass spectra and elemental analysis. Suitable monocrystals of cis-2-phenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3a), (2S,5S,6R)-2-phenyl-6-aza- 1,3-dioxa-5-sec butyl-2-borabenzocyclononen-4-one (3c) and 2,5-diphenyl-6-aza-1,3-dioxa-2-borabenzocyclononen-4-one (3h) were obtained and their structures are discussed. The X-ray structures, as well as the NMR data established that the configurations at the nitrogen and boron atoms are 'R' and 'S', respectively and the transannular fusion is cis. A semi-empirical (SAMI) study allowed calculation of the energy for all possible stereoisomers, showing that the stabilization increases as the THC (TetraHedral Character of the boron atom) increases and also as the N --> B bond distance decreases, in agreement with the experimental results. (C) 2002 Elsevier Science B.V. All rights reserved.