threo-(2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride

• 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
• 英文名称: threo-(2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride
• 英文别名: (2S*,3R*)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride salt；(2RS,3SR)-2-amino-3-hydroxy-3-phenyl-propionic acid ; hydrochloride；(2RS,3SR)-2-Amino-3-hydroxy-3-phenyl-propionsaeure; Hydrochlorid；(2R,3S)-2-amino-3-hydroxy-3-phenylpropanoic acid;hydrochloride
• 化学式: C₉H₁₁NO₃*ClH
• 分子量: 217.652
• InChiKey: VMVQTRSWQMRKDB-WLYNEOFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  threo-(2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride 以2.10 g的产率得到threo-(2S,3R)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  通过取代和优先结晶通过光学拆分制备旋光性（2RS，3SR）-2-氨基-3-羟基-3-苯基丙酸（苏-β-苯基丝氨酸）。

  摘要：

  通过取代和优先结晶，通过光学拆分获得旋光的苏--2-氨基-3-羟基-3-苯基丙酸（1），（2RS，3SR）-1盐酸盐[（2RS，3SR）-1的外消旋结构根据熔点，溶解度和红外光谱检查[HCl]。尽管在熔点下形成（2RS，3SR）-1.HCl，但仍以团块形式存在，尽管它在熔点形成外消旋化合物。在通过代替结晶的光学拆分中，使用L-苯丙氨酸甲酯盐酸盐（L-2）作为旋光活性共溶质时，优先从过饱和的外消旋溶液中结晶出（2R，3S）-1.HCl；使用D-2作为共溶质，提供了（2S，3R）-1.HCl，其光学纯度为95％。此外，通过优先结晶成功实现了光学拆分，从而连续获得光学纯度为90-92％的（2R，3S）-和（2S，3R）-1.HCl。从1-丙醇中重结晶纯化的（2R，3S）-和（2S，3R）-1.HCl用甲醇中的三乙胺处理，得到光学纯的（2R，3S）-和（2S，3R）-1。

  DOI：

  10.1248/cpb.54.1170
• 作为产物：
  描述：

  (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenylpropanoic acid 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 threo-(2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  Gymnangiamide, a Cytotoxic Pentapeptide from the Marine Hydroid Gymnangium regae

  摘要：

  A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.

  DOI：

  10.1021/jo0303113

文献信息

• Synthesis of fused tetramate-oxazolidine and -imidazolidine derivatives and their antibacterial activity
  作者：Liban Saney、Tharindi Panduwawala、Xiang Li、Kirsten E. Christensen、Miroslav Genov、Alexander Pretsch、Dagmar Pretsch、Mark G. Moloney

  DOI：10.1039/d3ob00594a

  日期：——

  A chemoselective route which provides direct access to bicyclic tetramates, making use of Dieckmann cyclisation of functionalised oxazolidines and imidazolidines derived from an aminomalonate, is reported; calculations suggest that the observed chemoselectivity is kinetically controlled and leads to the thermodynamically most stable product. Some compounds in the library showed modest antibacterial

  报道了一种化学选择性途径，该途径利用衍生自氨基丙二酸酯的官能化恶唑烷和咪唑烷的 Dieckmann 环化作用，可直接获得双环四酸酯；计算表明，观察到的化学选择性是动力学控制的，并导致热力学上最稳定的产物。库中的一些化合物对革兰氏阳性菌表现出适度的抗菌活性，并且这种活性在明确定义的化学空间区域中最大（554 < M w < 722 g mol -1；5.78 < cLogP < 7.16；788 < MSA < 972 Å 2；10.3 < 相对 PSA < 19.08)。
• Tetramate Derivatives by Chemoselective Dieckmann Ring Closure of <i>threo</i>-Phenylserines and Their Antibacterial Activity
  作者：Liban Saney、Kirsten E. Christensen、Xiang Li、Miroslav Genov、Alexander Pretsch、Dagmar Pretsch、Mark G. Moloney

  DOI：10.1021/acs.joc.2c01382

  日期：2022.9.16

  A general route, which provides direct access to substituted bicyclic tetramates, making use of Dieckmann cyclization of oxazolidines derived from threo-arylserines, is reported; the latter were found to be available by an efficient aldol-like reaction of glycine with some substituted benzaldehydes under alkaline conditions. The tetramates were found to release chelated metal cations acquired during

  报道了利用衍生自苏-芳基丝氨酸的恶唑烷的Dieckmann环化直接获得取代的双环四酸酯的一般途径；发现后者可通过甘氨酸与一些取代的苯甲醛在碱性条件下进行有效的类醛醇反应而获得。发现在通过温和的酸洗进行色谱纯化过程中，四联物释放螯合的金属阳离子。文库中的一些化合物对革兰氏阳性菌表现出良好的抗菌活性。化学信息学分析表明，最活跃的化合物符合 Ro5 标准，并且占据了一个狭窄的化学空间区域，与其他已知抗生素所占据的区域不同，最有效的化合物具有 399 < M w< 530 大; 3.5 < cLog P < 6.6; 594 < MSA <818 Å 2 ; 9.6 <相对。PSA <13.3%。当在 HSA 或血液存在下进行测试时，MIC 值转移到更高的浓度，但并未完全消除，这与血浆蛋白结合 (PPB) 效应一致。
• Gymnangiamide, a Cytotoxic Pentapeptide from the Marine Hydroid <i>Gymnangium</i> <i>r</i><i>egae</i>
  作者：Dennis J. Milanowski、Kirk R. Gustafson、Mohammad A. Rashid、Lewis K. Pannell、James B. McMahon、Michael R. Boyd

  DOI：10.1021/jo0303113

  日期：2004.4.1

  A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.
• Preparation of Optically Active (2RS,3SR)-2-Amino-3-hydroxy-3-phenylpropanoic Acid (threo-.BETA.-Phenylserine) via Optical Resolutions by Replacing and Preferential Crystallization
  作者：Tadashi Shiraiwa、Yuka Kawashima、Atsushi Ikaritani、Yumiko Suganuma、Reiichi Saijoh

  DOI：10.1248/cpb.54.1170

  日期：——

  the melting point. When, in optical resolution by replacing crystallization, L-phenylalanine methyl ester hydrochloride (L-2) was used as the optically active co-solute, (2R,3S)-1.HCl was preferentially crystallized from the supersaturated racemic solution; the use of D-2 as the co-solute afforded (2S,3R)-1.HCl with an optical purity of 95%. In addition, optical resolution by preferential crystallization

  通过取代和优先结晶，通过光学拆分获得旋光的苏--2-氨基-3-羟基-3-苯基丙酸（1），（2RS，3SR）-1盐酸盐[（2RS，3SR）-1的外消旋结构根据熔点，溶解度和红外光谱检查[HCl]。尽管在熔点下形成（2RS，3SR）-1.HCl，但仍以团块形式存在，尽管它在熔点形成外消旋化合物。在通过代替结晶的光学拆分中，使用L-苯丙氨酸甲酯盐酸盐（L-2）作为旋光活性共溶质时，优先从过饱和的外消旋溶液中结晶出（2R，3S）-1.HCl；使用D-2作为共溶质，提供了（2S，3R）-1.HCl，其光学纯度为95％。此外，通过优先结晶成功实现了光学拆分，从而连续获得光学纯度为90-92％的（2R，3S）-和（2S，3R）-1.HCl。从1-丙醇中重结晶纯化的（2R，3S）-和（2S，3R）-1.HCl用甲醇中的三乙胺处理，得到光学纯的（2R，3S）-和（2S，3R）-1。