(+/-)-3-butyryloxy-1-butyne

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-3-butyryloxy-1-butyne
• 英文别名: (RS)-3-butyryloxy-1-butyne；3-butyn-2-yl butyrate；Butanoic acid, but-3-yn-2-yl ester；but-3-yn-2-yl butanoate
• 化学式: C₈H₁₂O₂
• 分子量: 140.182
• InChiKey: HFKHPRPCSKQTCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-3-butyryloxy-1-butyne 在 Ps_. fluorescens hydrolase 作用下， 以 phosphate buffer 为溶剂， 反应 150.0h， 生成 (S)-(-)-3-丁炔-2-醇 、 (R)-(+)-3-丁炔-2-醇
  参考文献：
  名称：

  Rapid screening of hydrolases for the enantioselective conversion of ‘difficult-to-resolve’ substrates

  摘要：

  Hydrolases showing high enantio selectivity towards three racemic alcohols ( 1-methoxy-2-propanol, 3-hydroxy-tetrahydrofuran, 3-butyn-2-ol) and pantolactone were identified by a step-wise screening procedure. Initially, those biocatalysts, which exhibited hydrolytic activity towards the corresponding acetates or butyrates, were selected out of >100 enzymes. Here, rapid screening was performed in a pH-indicator-based format in microtiter plates. Subsequently, enantioselectivity of active hydrolases was determined in small scale reactions (similar to1 mg substrate per reaction) by means of gas chromatography using chiral columns. Enzymes exhibiting highest enantioselectivities were then chosen for preparative scale resolution. Using this strategy, at least one suitable hydrolase was found for 3 out of the 4 model compounds examined, allowing efficient kinetic resolution. Moreover, in all cases enantiocomplementary enzymes were identified thus enabling access to both enantiomers of all substrates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00465-1
• 作为产物：
  描述：

  丁酰氯 、 3-丁炔-2-醇 在 吡啶 作用下， 以69%的产率得到(+/-)-3-butyryloxy-1-butyne
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 3-butyn-2-ol

  摘要：

  Optically active 3-butyn-2-ol, an important building block, was synthesized successfully using lipase-catalyzed kinetic resolution. Starting from the thus obtained 3-butyn-2-ol, several 4-aryl-substituted compounds were synthesized enantioselectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00474-1

文献信息

• Discovery and Redesign of a Family VIII Carboxylesterase with High (<i>S</i>)-Selectivity toward Chiral <i>sec</i>-Alcohols
  作者：Areum Park、Seongsoon Park

  DOI：10.1021/acscatal.1c05410

  日期：2022.2.18

  Furthermore, the (S)-selectivity of PBE has been significantly improved by rational redesign based on molecular modeling. Molecular modeling identified a binding pocket composed of Ser381, Ala383, and Arg408 for the methyl substituent of (R)-1-phenylethyl acetate and suggested that larger residues may increase the enantioselectivity by interfering with the binding of the slow-reacting enantiomer. As predicted

  高度对映选择性脂肪酶已广泛用于通过动力学或动态动力学拆分制备通用的对映纯手性仲醇。脂肪酶本质上是( R )-选择性的，很难获得( S )-选择性脂肪酶。VIII 族羧酸酯酶的最新晶体结构表明，其催化三联体的空间阵列是脂肪酶的镜像，但催化三联体不同于脂肪酶。因此，我们假设 VIII 族羧酸酯酶可能对类似于 ( S ) 的仲醇表现出( S )-对映选择性。)-选择性丝氨酸蛋白酶，其催化三联体也在空间上排列为它的镜像。在这项研究中，制备了一种已知家族 VIII 羧酸酯酶（pdb 代码：4IVK）的同源酶（来自变形杆菌SG_bin9 的羧酸酯酶，PBE），该酶不仅对3-丁炔等仲醇具有中等的 ( S )-选择性。-2-醇和1-苯乙醇以及( R )-对所探索的底物中特定仲醇的选择性。此外，（S)-PBE 的选择性已通过基于分子模型的合理重新设计显着提高。分子模型确定了一个由 Ser381、Ala383
• Butinol i esterase
  申请人：Hauer Bernhard

  公开号：US20050181472A1

  公开（公告）日：2005-08-18

  The invention relates to novel proteins from Pseudomonas glumae , having esterase activity, in particular butynol I esterase activity, to nucleic acid sequences coding therefor, to expression cassettes, vectors and recombinant microorganisms; to methods for preparing said proteins and to the use thereof for enzymic, in particular enantioselective enzymic, ester hydrolysis or transesterification of organic esters.

  本发明涉及来自以下微生物的新型蛋白质 具有酯酶活性，特别是丁炔醇 I 酯酶活性的 其编码的核酸序列、表达盒、载体和重组微生物；制备所述蛋白质的方法，以及将其用于有机酯的酶解，特别是对映选择性酶解或酯交换反应。
• Lipase variants
  申请人：Matuschek Markus

  公开号：US20050255571A1

  公开（公告）日：2005-11-17

  The invention relates to a lipase variant which can be prepared by carrying out, on the amino acid sequence of a starting lipase selected from the lipase homologous family I.1 or I.2, at least one amino acid substitution in those positions which correspond to the positions 17, 29, 30, 52, 86, 117, 122, 160, 163, 167, 265, 266, 286, 289 in the prototype lipase sequence SEQ ID NO: 1.

  本发明涉及一种脂肪酶变体，可通过在选自脂肪酶同源家族 I.1 或 I.2 的起始脂肪酶的氨基酸序列上，在与原型脂肪酶序列 SEQ ID NO: 1 中的 17、29、30、52、86、117、122、160、163、167、265、266、286、289 位相对应的位置上进行至少一个氨基酸替换来制备。
• PROCESS FOR THE PREPARATION OF PROSTAGLANDIN PRECURSORS
  申请人：Chirotech Technology Limited

  公开号：EP1169467B1

  公开（公告）日：2010-02-17
• PROTEINS WITH ESTERASE ACTIVITY
  申请人：Breuer Michael

  公开号：US20100068760A1

  公开（公告）日：2010-03-18

  The invention relates to novel proteins having esterase activity, to mutants thereof, to nucleic acid sequences coding therefor, to expression cassettes, vectors and recombinant microorganisms; to methods for preparing said proteins and to the use thereof for enzymic, in particular enantioselective enzymic, ester hydrolysis or transesterification of organic esters.