S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸 | 5776-58-9

• 物质功能分类: 化学试剂 - 有机试剂 - 烯烃（环状与无环状）
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸
• 中文别名: b-D-吡喃葡萄糖苷,甲基2-脱氧-2-(1,3-二氢-1,3-二羰基-2H-异吲哚-2-基)-3,6-二-O-(苯基甲基)-
• 英文名称: acryloyl-CoA
• 英文别名: acrylyl-CoA；S-acryloyl-coenzyme-A；S-Acryloyl-coenzym-A；S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] prop-2-enethioate
• CAS: 5776-58-9
• 化学式: C₂₄H₃₈N₇O₁₇P₃S
• 分子量: 821.59
• InChiKey: POODSGUMUCVRTR-IEXPHMLFSA-N

物化性质

• 密度：
  1.86±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -5
• 重原子数：
  52
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  389
• 氢给体数：
  9
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸 在 β-alanyl-coa ammonia-lyase 、 氨 作用下， 生成 S-β-alanyl-coenzyme-A
  参考文献：
  名称：

  THE ENZYMATIC SYNTHESIS OF β-ALANYL COENZYME A

  摘要：

  DOI：

  10.1021/ja01626a108
• 作为产物：
  描述：

  (R)-lactyl-CoA 在 lactyl-CoA dehydratase from Clostridium propionicum 、 连二亚硫酸盐 、 5’-三磷酸腺苷 、 magnesium chloride 、 Cleland's reagent 作用下， 生成 S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸
  参考文献：
  名称：

  On the thermodynamic equilibrium between (R)-2-hydroxyacyl-CoA and 2-enoyl-CoA

  摘要：

  A combined experimental and computational approach has been applied to investigate the equilibria between several α‐hydroxyacyl‐CoA compounds and their 2‐enoyl‐CoA derivatives. In contrast to those of their β, γ and δ counterparts, the equilibria for the α‐compounds are relatively poorly characterized, but qualitatively they appear to be unusually sensitive to substituents. Using a variety of techniques, we have succeeded in measuring the equilibrium constants for the reactions beginning from 2‐hydroxyglutaryl‐CoA and lactyl‐CoA. A complementary computational evaluation of the equilibrium constants shows quantitative agreement with the measured values. By examining the computational results, we arrive at an explanation of the substituent sensitivity and provide a prediction for the, as yet unmeasured, equilibrium involving 2‐hydroxyisocaproyl‐CoA.

  DOI：

  10.1111/j.1742-4658.2010.07597.x
• 作为试剂：
  描述：

  乙酰辅酶A 、 乙酸盐 、 在 H-CoA 、 5’-三磷酸腺苷 、 辅酶 A 、 乙酰辅酶A 、 S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸 作用下， 40.0 ℃ 、1733.19 MPa 条件下， 反应 9.67h， 生成 S-[2-[3-[[4-[[[(2R,3S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-羟基-3-膦酰氧基四氢呋喃-2-基]甲氧基-羟基磷酰]氧基-羟基磷酰]氧基-2-羟基-3,3-二甲基丁酰基]氨基]丙酰氨基]乙基]硫代丙-2-烯酸
  参考文献：
  名称：

  Biocatalytic manufacturing of (meth) acrylylcholine or 2-(N, N-dimethylamino) ethyl (meth) acrylate

  摘要：

  一种生物催化合成2-(N,N-二甲基氨基)乙醇和/或丙烯酸和/或甲基丙烯酸的胆碱酯的方法，包括在具有胆碱乙酰转移酶活性的生物催化剂存在下，将2-(N,N-二甲基氨基)乙醇和/或胆碱与丙烯酰辅酶A和/或甲基丙烯酰辅酶A反应。丙烯酰辅酶A和/或甲基丙烯酰辅酶A是在ATP和具有S-乙酰辅酶A合成酶活性的生物催化剂存在下，通过丙烯酸和/或甲基丙烯酸与辅酶A反应形成的。

  公开号：

  US07754455B2

文献信息

• [EN] MICROORGANISMS FOR PRODUCING 4C-5C COMPOUNDS WITH UNSATURATION AND METHODS RELATED THERETO<br/>[FR] MICRO-ORGANISMES POUR LA PRODUCTION DE COMPOSÉS EN 4C-5 C AVEC UNE INSATURATION ET PROCÉDÉS ASSOCIÉS
  申请人：GENOMATICA INC

  公开号：WO2016004334A1

  公开（公告）日：2016-01-07

  The invention provides a non-naturally occurring microbial organism having a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol, pathway. The microbial organism contains at least one exogenous nucleic acid encoding an enzyme in a pathway. The invention additionally provides a method for producing butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol,. The method can include culturing a butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol-producing microbial organism, where the microbial organism expresses at least one exogenous nucleic acid encoding a pathway enzyme in a sufficient amount, and under conditions and for a sufficient period of time to produce butadiene, crotyl alcohol, 2,4-pentadienoate, 3-buten-2-ol, or 3-buten-1-ol.

  该发明提供了一种具有丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇途径的非自然微生物生物体。该微生物生物体含有至少一个编码途径中酶的外源核酸。该发明还提供了一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的方法。该方法可以包括培养一种生产丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇的微生物生物体，其中该微生物生物体表达至少一个编码途径酶的外源核酸，且在足够的量下，在适当的条件和足够的时间内产生丁二烯、丁烯醇、2,4-戊二烯酸酯、3-丁烯-2-醇或3-丁烯-1-醇。
• [EN] ENZYMATIC PRODUCTION OF ACRYLYL-COA OR ETHYLENE FROM GLYCEROL<br/>[FR] PRODUCTION ENZYMATIQUE D'ACRYLYL-COA OU D'ÉTHYLÈNE À PARTIR DE GLYCÉROL
  申请人：GLOBAL BIOENERGIES

  公开号：WO2016097289A1

  公开（公告）日：2016-06-23

  Described is a method for the production of acrylyl-CoA from glycerol comprising the following steps: (a) the enzymatic conversion of glycerol into 3-hydroxypropionaldehyde; (b) the enzymatic conversion of said 3-hydroxypropionaldehyde into 3-hydroxypropionyl-CoA; and (c) the enzymatic conversion of said 3-hydroxypropionyl-CoA into acrylyl-CoA. Further enzymatic conversion of acrylyl-CoA into other products are disclosed. Further described is a method for the production of ethylene comprising the enzymatic conversion of propionic acid into ethylene. It is described that the enzymatic conversion of propionic acid into ethylene can be achieved by making use of a cytochrome P450 fatty acid decarboxylase or a non-heme iron oxygenase. Further, it is described that said propionic acid can be obtained by the enzymatic conversion of acrylyl-CoA into said propionic acid.

  描述了一种从甘油生产丙烯酰辅酶A的方法，包括以下步骤：(a) 将甘油酶转化为3-羟基丙醛；(b) 将所述3-羟基丙醛酶转化为3-羟基丙酰辅酶A；以及(c) 将所述3-羟基丙酰辅酶A酶转化为丙烯酰辅酶A。进一步披露了丙烯酰辅酶A的进一步酶转化为其他产品的方法。进一步描述了一种生产乙烯的方法，包括将丙酸酶转化为乙烯。描述了通过利用细胞色素P450脂肪酸脱羧酶或非血红素铁氧酶将丙酸酶转化为乙烯的方法。此外，还描述了通过将丙烯酰辅酶A酶转化为所述丙酸来获得所述丙酸的方法。
• [EN] METHYLENEMALONIC ACID AND INTERMEDIATES, PROCESSES FOR THEIR PREPARATION AND ENGINEERED MICROORGANISMS<br/>[FR] ACIDE MÉTHYLÈNEMALONIQUE ET INTERMÉDIAIRES, PROCÉDÉS POUR LEUR PRÉPARATION ET MICRO-ORGANISMES MODIFIÉS
  申请人：BIOAMBER INC

  公开号：WO2018018151A1

  公开（公告）日：2018-02-01

  The description relates to, inter alia, recombinant microorganisms, engineered metabolic pathways, chemical catalysts, and products produced through the use of the described methods and materials. The products produced include methylenemalonic acid and intermediates, as well as their salts and esters.

  该描述涉及重组微生物、工程代谢途径、化学催化剂以及通过所述方法和材料生产的产品。所生产的产品包括亚甲基丙二酸和中间体，以及它们的盐和酯。
• Biocatalytic manufacturing of (meth) acrylic esters
  申请人：Symes Kenneth Charles

  公开号：US20090130729A1

  公开（公告）日：2009-05-21

  The invention relates to a biocatalytic method or process for the synthesis of esters of acrylic acid and/or methacrylic acid free of positively chargeable/charged groups, comprising reacting one or more alcohols (alcohol starting materials) which are free of positively chargeable or charged groups with (meth)acrylyl-CoA, preferably in the presence of a catalyst (inorganic, organic or organometallic, or preferably a biocatalyst) capable of effecting the transfer of an alcohol radical from an alcohol starting material as defined above or below to (meth)acrylyl CoA under removal of the CoA moiety transferase activity, such as an enzyme of the transferase or hydrolase class of enzymes. The (meth)acrylyl-CoA is preferably formed by reaction of (meth)acrylic acid or its salts with coenzyme A in the presence of an energy providing substance and a biocatalyst e.g. with S-acetyl coenzyme A synthetase activity or by reaction of acrylate or methacrylate produced metabolically in the presence of a biocatalyst or metabolically.

  本发明涉及一种生物催化合成丙烯酸酯和/或甲基丙烯酸酯的方法或过程，不含正电荷/带电基团，包括将一个或多个醇（醇起始物质），其不含正电荷或带电基团，与（甲基）丙烯酰辅酶A反应，优选在催化剂（无机、有机或有机金属，或优选的生物催化剂）的存在下，能够实现从上述或下述定义的醇起始物质中转移醇基团至（甲基）丙烯酰辅酶A，去除CoA基团转移酶活性，例如转移酶或水解酶类酶。其中（甲基）丙烯酰辅酶A优选由（甲基）丙烯酸或其盐与辅酶A在能量提供物和生物催化剂的存在下反应形成，例如具有S-乙酰辅酶A合成酶活性的酶，或在生物催化剂或代谢产物的存在下代谢产生丙烯酸酯或甲基丙烯酸酯。
• MICROORGANISMS AND METHODS FOR THE BIOSYNTHESIS OF FUMARATE, MALATE, AND ACRYLATE
  申请人：Burk Mark J.

  公开号：US20100009419A1

  公开（公告）日：2010-01-14

  A non-naturally occurring eukaryotic or prokaryotic organism includes one or more gene disruptions occurring in genes encoding enzymes imparting increased fumarate, malate or acrylate production in the organism when the gene disruption reduces an activity of the enzyme. The one or more gene disruptions confers increased production of acrylate onto the organism. Organisms that produce acrylate have an acrylate pathway that at least one exogenous nucleic acid encoding an acrylate pathway enzyme expressed in a sufficient amount to produce acrylate, the acrylate pathway comprising a decarboxylase. Methods of producing fumarate, malate or acrylate include culturing these organisms.

  非自然发生的真核或原核生物包括一个或多个基因干扰，这些基因编码酶，在酶的活性降低时，增加富马酸、苹果酸或丙烯酸的生产。这些一个或多个基因干扰赋予生物更高的丙烯酸产量。生产丙烯酸的生物具有丙烯酸途径，其中至少一个外源核酸编码的丙烯酸途径酶表达量足以产生丙烯酸，丙烯酸途径包括一个脱羧酶。生产富马酸、苹果酸或丙烯酸的方法包括培养这些生物。