2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid | 155179-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid
• 英文别名: 2-(phenylmethoxycarbonylamino)-4-phosphonobutanoic acid
• CAS: 155179-92-3
• 化学式: C₁₂H₁₆NO₇P
• 分子量: 317.235
• InChiKey: HFPGWCFPNIQOKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  sodium hydroxide 、 2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid 以 水 为溶剂， 生成 2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid monosodium salt
  参考文献：
  名称：

  PHOSPHONIC ACID DIESTER DERIVATIVE AND METHOD FOR PRODUCING THEREOF

  摘要：

  一个由下列一般公式（1）表示的膦酸二酯衍生物，其中R1和R2中至少有一个表示一个离去基团。

  公开号：

  US20090163725A1
• 作为产物：
  描述：

  2-氨基-4-膦酰丁酸 、 氯甲酸苄酯 在 sodium hydroxide 、 碳酸氢钠 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 15.0h， 生成 2-(N-benzyloxycarbonylamino)-4-phosphonobutanoic acid
  参考文献：
  名称：

  PHOSPHONIC ACID DIESTER DERIVATIVE AND METHOD FOR PRODUCING THEREOF

  摘要：

  一个由下列一般公式（1）表示的膦酸二酯衍生物，其中R1和R2中至少有一个表示一个离去基团。

  公开号：

  US20090163725A1

文献信息

• NAHLSGEN OPTICAL RESOLUTION METHOD
  申请人：KYOTO UNIVERSITY

  公开号：US20190225634A1

  公开（公告）日：2019-07-25

  Provided is a method for separating the four optical isomers of Nahlsgen. The method according to the present invention for producing a mixture of a D-2-amino-4-[(Rp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate and an L-2-amino-4-[(Sp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate includes subjecting a mixture of the four optical isomers, represented by Formula (1′), to fractional crystallization from water or from a solvent mixture of water and a water-soluble organic solvent, to precipitate a mixture of a compound represented by Formula (1-1′-1) and a compound represented by Formula (1-4′-1), where Formulae (1′), (1-1′-1), and (1-4′-1) are expressed as follows:

  提供了一种分离Nahlsgen的四种光学异构体的方法。根据本发明的方法，用于产生一种D-2-氨基-4-[(Rp)-(3-羧甲基苯氧基)(甲氧基)磷酰基]丁酸水合物和一种L-2-氨基-4-[(Sp)-(3-羧甲基苯氧基)(甲氧基)磷酰基]丁酸水合物的混合物的方法包括将由式（1′）表示的四种光学异构体的混合物经过从水或水和水溶性有机溶剂的溶剂混合物中的分馏结晶，以沉淀出由式（1-1′-1）和式（1-4′-1）表示的化合物的混合物，其中式（1′）、（1-1′-1）和（1-4′-1）的式如下所示：
• Phosphonic acid diester derivative and method for producing thereof
  申请人：——

  公开号：US08129557B2

  公开（公告）日：2012-03-06

  A phosphonic acid diester derivative represented by the following general formula (1): wherein at least one of R1 and R2 denotes a leaving group.

  一种磷酸二酯衍生物，其通式表示为（1）：其中R1和R2中至少一个表示为离去基团。
• Nahlsgen optical resolution method
  申请人：KYOTO UNIVERSITY

  公开号：US10774098B2

  公开（公告）日：2020-09-15

  Provided is a method for separating the four optical isomers of Nahlsgen. The method according to the present invention for producing a mixture of a D-2-amino-4-[(Rp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate and an L-2-amino-4-[(Sp)-(3-carboxymethylphenoxy)(methoxy)phosphoryl]butanoic acid hydrate includes subjecting a mixture of the four optical isomers, represented by Formula (1′), to fractional crystallization from water or from a solvent mixture of water and a water-soluble organic solvent, to precipitate a mixture of a compound represented by Formula (1-1′-1) and a compound represented by Formula (1-4′-1), where Formulae (1′), (1-1′-1), and (1-4′-1) are expressed as follows:

  本发明提供了一种分离 Nahlsgen 四种光学异构体的方法。根据本发明，生产 D-2-氨基-4-[(Rp)-(3-羧甲基苯氧基)(甲氧基)磷酰]丁酸水合物和 L-2-氨基-4-[(Sp)-(3-羧甲基苯氧基)(甲氧基)磷酰]丁酸水合物混合物的方法包括将式（1′）表示的四种光学异构体的混合物、从水中或从水和水溶性有机溶剂的混合溶剂中进行分馏结晶，析出由式(1-1′-1)表示的化合物和由式(1-4′-1)表示的化合物的混合物，其中式(1′)、(1-1′-1)和(1-4′-1)表示如下：
• Synthesis and separation of a diastereomeric pair of phosphonopeptide inhibitors of the cyclic AMP-dependent protein kinase catalytic subunit
  作者：Chunhua Yang、Raheel Qamar、Scott J. Norton、Paul F. Cook、David E. Minter

  DOI：10.1016/s0040-4020(01)85056-0

  日期：1994.2

  In this paper we report the establishment of a novel procedure to synthesize a nonhydrolyzable phosphonopeptide dead-end inhibitor of the catalytic subunit of cAMP-dependent protein kinase. This procedure has been optimized to maximize the peptide yield and gives a diastereomeric pair of heptapeptides that can be separated on a C-18 reverse phase HPLC column. The two peptides have been characterized by NMR and the ability of these peptides to inhibit the reaction of the catalytic subunit of cAMP-dependent protein kinase. Peptide A has a dissociation constant of 9 micromolar, and is a 10-fold better inhibitor as compared to peptide B. On the basis of this 10-fold greater inhibition afforded by peptide A, this peptide is assigned the all L-form configuration. It is expected that this procedure can easily be adapted to synthesize a variety of different peptide inhibitors which involve a nonhydrolyzable phosphate on an amino acid.
• Investigation of Mechanism of Nitrogen Transfer in Glucosamine 6-Phosphate Synthase with the Use of Transition State Analogs
  作者：Sławomir Milewski、Maria Hoffmann、Ryszard Andruszkiewicz、Edward Borowski

  DOI：10.1006/bioo.1997.1077

  日期：1997.10

  Several structural analogs of putative tetrahedral intermediates of the reaction catalysed by the glutamine amide transfer domain of Candida albicans glucosamine 6-phosphate synthase have been designed and synthesized. Esters and amides of gamma-phosphonic and gamma-sulfonic analogs of glutamine and glutamic acid were tested as potential inhibitors of the enzyme. N-substituted amides 9 and 15 were found to be the strongest inhibitors in the series. Structure-activity relationship studies led to conclusions supporting the possibility of a direct nucleophilic attack of the glutamine amide nitrogen on an electrophilic site of the enzyme-bound fructose 6-phosphate as the most likely mechanism of nitrogen transfer in glucosamine 6-phosphate synthase. (C) 1997 Academic Press.