methyl (-)-(S)-5-oxotetrahydro-3-furancarboxylate | 4694-67-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: methyl (-)-(S)-5-oxotetrahydro-3-furancarboxylate
• 英文别名: S-(-)-methyl paraconate；(S)-paraconic acid methyl ester；(S)-Methyl 5-oxotetrahydrofuran-3-carboxylate；methyl (3S)-5-oxooxolane-3-carboxylate
• CAS: 4694-67-1
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: YPVWDFLEJHZAHZ-BYPYZUCNSA-N

物化性质

• 沸点：
  266.1±33.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-氧代环丁烷甲酸甲酯 在 2,3,4,5,6-pentahydroxy-hexanal 、 GDH 、 氧气 、 FAD 、 phenylacetone monooxygenase from Thermobifida fusca, mutant with F₄₄₁/T₄₄₂ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以90%的产率得到
  参考文献：
  名称：

  Engineering of a Baeyer‐Villiger monooxygenase to Improve Substrate Scope, Stereoselectivity and Regioselectivity

  摘要：

  Baeyer‐Villiger monooxygenases belong to a family of flavin‐binding proteins that catalyze the Baeyer‐Villiger (BV) oxidation of ketones to produce lactones or esters, which are important intermediates in pharmaceuticals or sustainable materials. Phenylacetone monooxygenase (PAMO) from Thermobifida fusca with moderate thermostability catalyzes the oxidation of aryl ketone substrates, but is limited by high specificity and narrow substrate scope. In the present study, we applied loop optimization by loop swapping followed by focused saturation mutagenesis in order to evolve PAMO mutants capable of catalyzing the regioselective BV oxidation of cyclohexanone and cyclobutanone derivatives with formation of either normal or abnormal esters or lactones. We further modulated PAMO to increase enantioselectivity. Crystal structure studies indicate that rotation occurs in the NADP‐binding domain and that the high B‐factor region is predominantly distributed in the catalytic pocket residues. Computational analyses further revealed dynamic character in the catalytic pocket and reshaped hydrogen bond interaction networks, which is more favorable for substrate binding. Our study provides useful insights for studying enzyme‐substrate adaptations.

  DOI：

  10.1002/cbic.202400328

文献信息

• Chemoenzymatic synthesis of enantioenriched 5-oxo-tetrahydro-3-furancarboxylic acid derivatives
  作者：Andrea Comini、Cristina Forzato、Patrizia Nitti、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2004.01.001

  日期：2004.2

  (R)-(+)-Paraconic acid 4, (S)-(−)-terebic acid 6 and their corresponding methyl and ethyl esters having ee’s ranging from 60% to 92% were obtained by enzymatic resolution of their racemates. The enzymatic resolution of racemic ethyl γ-methylparaconates 14a and 14b allowed the isolation of the unreacted ester (2R,3R)-(+)-14a and that of the lactonic acid (2S,3R)-(−)-5b with 80% and 93% ee, respectively

  通过消旋的外消旋物，获得（ee）范围为60％至92％的（R）-（+）-对ac酸4，（S）-（-）-对苯二甲酸6及其相应的甲酯和乙酯。外消旋的γ-甲基对羟基苯甲酸乙酯14a和14b的酶解可分离未反应的酯（2 R，3 R）-（+）- 14a和内酯酸（2 S，3 R）-（-）- 5b的ee分别为80％和93％ee，前者使用马肝丙酮粉（HLAP），后者使用α-胰凝乳蛋白酶（α-CT）。对映体乙基（2通过面包酵母的乙酰丁二酸二乙酯的还原反应，获得了ee> 99％的S，3 S）-（-）- 14a和（2 S，3 R）-（-）- 14b。
• Ichihara, Akitami; Kawagishi, Hirokazu; Sasagawa, Tadakazu, Agricultural and Biological Chemistry, 1981, vol. 45, # 9, p. 2163 - 2164
  作者：Ichihara, Akitami、Kawagishi, Hirokazu、Sasagawa, Tadakazu、Sakamura, Sadao

  DOI：——

  日期：——