2-(diisopropoxyphosphoryl)propanoic acid | 1426294-32-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 2-(diisopropoxyphosphoryl)propanoic acid
• 英文别名: 2-Di(propan-2-yloxy)phosphorylpropanoic acid；2-di(propan-2-yloxy)phosphorylpropanoic acid
• CAS: 1426294-32-7
• 化学式: C₉H₁₉O₅P
• 分子量: 238.221
• InChiKey: VJFJVFITXXAVKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(diisopropoxyphosphoryl)propanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library

  摘要：

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.

  DOI：

  10.1021/co400003d
• 作为产物：
  描述：

  ethyl 2-(diisopropylphosphono)propionate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 2-(diisopropoxyphosphoryl)propanoic acid
  参考文献：
  名称：

  Column Chromatography-Free Solution-Phase Synthesis of a Natural Piper-Amide-like Compound Library

  摘要：

  We have achieved an efficient solution-phase parallel synthesis of a library of natural piper-amide-like compounds from the bifunctional beta-phosphono-N-hydroxy-succinimidyl ester intermediate. The primary important feature in our study is the construction of natural-product-like molecules through the adaptation of sophisticated organic reactions that create water-soluble byproducts for a chromatography-free purification. This simple and efficient method rapidly provides a combinatorial library of high yield and purity. The library was evaluated against GPCR targets to demonstrate its potential use as a tool for drug discovery and in chemical biology.

  DOI：

  10.1021/co400003d

文献信息

• A Dehydratase Domain in Ambruticin Biosynthesis Displays Additional Activity as a Pyran-Forming Cyclase
  作者：Gesche Berkhan、Frank Hahn

  DOI：10.1002/anie.201407979

  日期：2014.12.15

  Hydropyran rings are a common structural motif in reduced polyketides. Information on their biosynthetic formation and particularly the biochemical characterization of the responsible enzymes has only been reported in few cases. The dehydratase domain AmbDH3 from the ambruticin polyketide synthase was investigated. Through in vitro assay of the recombinant domain with synthetically‐derived substrate

  氢吡喃环是还原的聚酮化合物中的常见结构基序。关于它们的生物合成形成的信息，尤其是负责的酶的生化特性的信息仅在少数情况下得到了报道。研究了来自安布提菌素聚酮化合物合酶的脱水酶结构域AmbDH3。通过使用合成来源的底物替代物对重组结构域进行体外分析，结果表明它具有环氧化酶的第二种催化活性，可进行加氧杂合物的添加。用合成底物类似物探测AmbDH3在两个子步骤中均显示出立体选择性和底物耐受性。这是从顺式吡喃形成环化酶的第一个特征‐AT PKS系统和具有这种双重活性的聚酮化合物合酶结构域的首次报告。最后，揭示了该结构域显示出在化学酶促合成中的应用潜力。
• Insights into the Dual Activity of a Bifunctional Dehydratase-Cyclase Domain
  作者：Kwang Hoon Sung、Gesche Berkhan、Tim Hollmann、Lisa Wagner、Wulf Blankenfeldt、Frank Hahn

  DOI：10.1002/anie.201707774

  日期：2018.1.2

  significantly to their biological activity. Here, we report structural and mechanistic investigations on AmbDH3, a polyketide synthase domain with dual activity as dehydratase (DH) and pyran‐forming cyclase in ambruticin biosynthesis. AmbDH3 is similar to monofunctional DH domains, using H51 and D215 for dehydration. V173 was confirmed as a diagnostic residue for cyclization activity by a mutational study and

  含氧杂环是聚酮化合物天然产物中常见的结构基序，对它们的生物活性有重要贡献。在这里，我们报告了AmbDH3的结构和机理研究，AmbDH3是一种在琥珀酸生物素合成中具有脱水酶（DH）和吡喃形成环化酶双重活性的聚酮化合物合酶结构域。AmbDH3类似于单功能DH域，使用H51和D215进行脱水。通过突变研究和酶促体外实验，证实V173为环化活性的诊断残基。在看似单功能的AmbDH2中观察到类似的基序，该基序也显示出意想不到的环化酶活性。我们的结果为生物合成途径中隐藏的环化酶的挖掘铺平了道路。
• [EN] PIPER AMIDE-BASED COMPOUND AS BOMBESIN RECEPTOR SUBTYPE 3<br/>[FR] COMPOSÉ À BASE D'AMIDE DE LA PLANTE DU GENRE PIPER UTILISÉ COMME RÉCEPTEUR DE BOMBÉSINE DE SOUS-TYPE 3
  申请人：SNU R&DB FOUNDATION

  公开号：WO2014129874A1

  公开（公告）日：2014-08-28

  본 발명은 신규한 α,β-불포화 아미드 화합물; 하나 이상의 α,β-불포화 아미드 화합물을 포함하는 화합물 라이브러리로부터 비만 예방 또는 치료효과를 나타내는 화합물을 선별하는 단계 및 상기 선별된 화합물을 함유하는 비만 예방 또는 치료용 조성물을 제조하는 단계를 포함하는 것이 특징인 비만 예방 또는 치료용 조성물 제조 방법; 및 α,β-불포화 아미드 화합물을 포함하는 비만 예방 또는 치료용 조성물에 관한 것이다. 본 발명의 α,β-불포화 아미드 화합물은 다양한 활성을 나타내는 천연물인 파이퍼 아미드를 모방하는 모핵구조를 가지는 화합물로서 다양한 약리활성을 나타낼 수 있을 것이며, 중간 산물로서 β-포스포노-N-히드록시숙신이미딜 에스테르(β-phosphono-N-hydroxysuccinimidyl ester)를 이용하여 가용성 부산물(by-products)을 생성하므로 통상적으로 이용되는 컬럼 크로마토그래피 정제과정을 수행할 필요없이 순수한 화합물을 획득할 수 있다. 또한 이렇게 합성된 화합물 라이브러리로부터 약리활성을 테스트하여 BRS-3에 대한 작용제인 화합물들을 스크리닝하여 비만 예방 또는 치료용 조성물로 유용하게 활용할 수 있다.