(2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid | 23150-29-0

• 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: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid
• 英文别名: (2S,3R)-3-[4-(methylthio)phenyl]serine；D-threo-3-(4-methylthiophenyl)serine；(2S,3R)-2-amino-3-hydroxy-3-(4-methylsulfanylphenyl)propanoic acid
• CAS: 23150-29-0
• 化学式: C₁₀H₁₃NO₃S
• 分子量: 227.284
• InChiKey: SPZMWQYXIJSYBO-DTWKUNHWSA-N

物化性质

• 沸点：
  462.5±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid 在 sodium tetrahydroborate 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis of 4-Sulfur-Substituted (2S,3R)-3-Phenylserines by Enzymatic Resolution. Enantiopure Precursors for Thiamphenicol and Florfenicol

  摘要：

  Enantiomerically pure 4-methylthio- and 4-methylsulfonyl-substituted (2S,3R)-3-phenylserines are prepared by enzymatic resolution of the corresponding racemic three almides using the amidase from Ochrobactrum anthropi NCIMB 40321. The unwanted (2R,3S) enantiomers of the amides are separated from the enantiopure amino acids and easily racemized after Schiff base formation with the corresponding 4-(methylthio)- and 4-(methylsulfonyl)benzaldehyde. The racemization can be combined with the preparation of the racemic amides by aldol reaction under crystallization conditions to yield only the threo isomers. Enantiopure (2S, 3R)-3-[4-(methylthio)phenyl]serine and (2S,3R)-3-[4-(methylsulfonyl)phenyl are thus obtained in 78% and 62% overall yields starting from the corresponding substituted benzaldehydes, (2S,3R)-3-[4-(methylsulfonyl)phenyl]serine is reduced to (1R,2R)-2-amino-1-[4-(methylthio)phenyl]propane-1,3-diol with NaBH4/H2SO4 and can be used for the synthesis of thiamphenicol and florfenicol.

  DOI：

  10.1021/op970045t
• 作为产物：
  描述：

  DL-threo-3-(4-methylthiophenyl)serine 在 盐酸 作用下， 以 水 为溶剂， 反应 5.0h， 生成 (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid
  参考文献：
  名称：

  An Enzymatic Route to Florfenicol

  摘要：

  通过使用灰葡萄链霉菌的蛋白酶进行酶水解，外消旋的苏氨酰-3-（4-甲硫基苯基）丝氨酸乙酯被分解，两种立体异构体都转化为 D-苏氨酰-4，5-二氢-5-（4-甲磺酰基苯基）-2-苯基-4-恶唑甲醇，从而正式合成了氟苯尼考。

  DOI：

  10.1055/s-1991-26603

文献信息

• ASYMMETRIC PROCESS FOR PREPARING FLORFENICOL, THIAMPHENICOL, CHLORAMPHENICOL AND OXAZOLINE INTERMEDIATES
  申请人：SCHERING CORPORATION

  公开号：EP0674618A1

  公开（公告）日：1995-10-04
• ENGINEERED ALDOLASE POLYPEPTIDES AND USES THEREOF
  申请人：Enzymaster (Ningbo) Bio-Engineering Co., Ltd

  公开号：US20200123525A1

  公开（公告）日：2020-04-23

  The present invention provides engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The present disclosure also provides polynucleotides encoding engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides of the present invention for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. So, it has good industrial application prospects.
• ENGINEERED POLYPEPTIDES AND THEIR APPLICATIONS IN THE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS
  申请人：Enzymaster (Ningbo) Bio-Engineering Co., Ltd.

  公开号：US20210284987A1

  公开（公告）日：2021-09-16

  The present invention provides engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The engineered polypeptides disclosed in this invention were developed through directed evolution based on the ability of catalytic synthesis of (2S, 3R)-2-amino-3-hydroxy-3-(4-nitrophenyl) propanoic acid. The present disclosure also provides polynucleotides encoding engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides of the present invention for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. So, it has good industrial application prospects.
• US5352832A
  申请人：——

  公开号：US5352832A

  公开（公告）日：1994-10-04
• [EN] ASYMMETRIC PROCESS FOR PREPARING FLORFENICOL, THIAMPHENICOL, CHLORAMPHENICOL AND OXAZOLINE INTERMEDIATES<br/>[FR] PROCEDE ASYMETRIQUE DE PREPARATION DE FLORFENICOL, THIAMPHENICOL, CHLORAMPHENICOL ET D'INTERMEDIAIRES D'OXAZOLINE
  申请人：——

  公开号：WO1994014764A1

  公开（公告）日：1994-07-07

  [EN] The present invention comprises a process for the asymmetric synthesis of florfenicol, thiamphenicol or chloramphenicol. In an alternative embodiment, the present invention comprises a process for isomerizing of the S,S-isomer of florfenicol to the R,S-isomer (I) by sequentially treating with: (i) a lower alkylsulfonyl chloride and a tertiary amine base; (ii) sulfuric acid and water; (iii) an alkali metal hydroxide. The present invention further comprises a process for regioselectively opening an epoxide to form a threo-oxazoline.
  [FR] La présente invention concerne un procédé de synthèse asymétrique de florfénicol, thiamphénicol ou chloramphénicol. Dans un autre mode de réalisation, la présente invention concerne un procédé permettant d'isomériser S,S-isomère de florfénicol par rapport à R,S-isomère (I) en le traitant successivement avec: (i) un chlorure d'alkylsulfonyle inférieur et une base amine tertiaire; (ii) de l'acide sulfurique et de l'eau; (iii) un hydroxyde de métaux alcalins. La présente invention concerne en outre un procédé permettant l'ouverture régiosélective d'un époxyde pour obtenir une thréo-oxazoline.