CAS: 617-12-9; Chorismicacid

该化合物是一种芳香化合物,在各种自然产品的生物合成中发挥着关键作用,特别是在对合成氨基酸(如苯丙烯酸,亚硝酸和酸)等氨基酸在植物和微生物中的合成至关重要的香酸途径中.它是一种白色晶状固体,由于存在碳本体酸功能组,在水和酸性成分中可溶解.它的特点在于它能够进行各种化学反应,包括解剖和重新排列,从而形成其他重要的生化中间体.它的结构特征是具有多种功能组的双循环系统,有助于其再活动性和生物意义.此外,铬酸是合成各种次级代谢物(包括对于植物防御机制和生态互动至关重要的碱和氟芳基物)的前体.

结构式图片

欧盟法规

ECHA物质C&L通报

上下游产品

CAS号87664-40-2 prephenic acid | CAS号99-96-7 4-羟基苯甲酸 | CAS号118-92-3 邻氨基苯甲酸 | CAS号156-06-9 苯丙酮酸

合成工艺路线路线简述

  • 合成目标产物 Chorismic Acid 主要起始原料 Methyl (-)-Shikimate
  • (文献来源)合成步骤主要原料 Methyl (-)-Shikimate
Methyl Shikimate置于sodium Dithionite,Magnesium Sulfate Sodium Hydroxide,Pkad50,Adenosine 5'-Triphosphate Sodium Salt,2,6-蒽二酚体系中,用 四氢呋喃,Sodium Hydroxide 作为反应溶剂,化学反应 9.0H,反应生成 分支酸
参考文献:同位素对分支酸酶促和非酶促反应的影响
标题:同位素对分支酸酶促和非酶促反应的影响
摘要:重要的生物合成中间体分支酸通过两种竞争性途径进行热反应,一种通过消除烯醇丙酮酸侧链产生 4-羟基苯甲酸酯,另一种通过简单的克莱森重排进行预苯甲酸酯化.用同位素标记的分支酸衍生物进行的测量表明,两者都是由烯醇丙酮酸基团的方向控制的协调的 Sigmatropic 过程.在 [4-2H] 分支酸的消除反应中,在 60 摄氏度 3 小时后发现大约 60% 的标记存在于丙酮酸中.此外,1.846 +/-0.057 2H 同位素效应对转移的氢原子和 1.0374 + /-0.0005 醚氧的 18O 同位素效应表明该过程的过渡态是高度不对称的,氢原子从 C4 到 C9 的转移明显不如 Co 键断裂.在竞争的克莱森重排中,确定了在键断裂位置 (1.0482 +/-0.0005) 的非常大的 18O 同位素效应和在键合位置 (1.0118 +/-0.0004) 的较小的 13C 同位素效应.类似量
DOI:10.1021/ja052929V

海关参考信息

专利信息


专利号:US-12421534-B2
优先权日:2021-11-10
标 题 :Engineered enzymes and method for the synthesis of diverse tyrosine analogs
发明人:ALMHJELL PATRICK J; ARNOLD FRANCES H
权利人:CALIFORNIA INST OF TECHN
摘要:Provided herein is an engineered tryptophan synthase β-subunit (TrpB) that catalyzes the synthesis of tyrosine, tyrosine analogs, or salts thereof. Also provided herein are methods for preparing tyrosine, tyrosine analogs, or a salt thereof using the engineered TrpB described herein.

专利号:US-5798236-A
优先权日:1992-09-30
标 题 :Synthesis of quinic acid from glucose
发明人:FROST JOHN W; DRATHS KAREN M; WARD TIMOTHY L
权利人:GENENCOR INT
摘要:There are described methods for the synthesis of quinoid organic compounds from a renewable energy source such as glucose. The method comprises enhancing the amount of glucose equivalents introduced into the pathway, blocking the common pathway so as to accumulate dehydroquinate and converting the dehydroquinate to quinic acid.

专利号:US-5272073-A
优先权日:1992-06-30
标 题 :Biocatalytic synthesis of catechol from glucose
发明人:FROST JOHN W; DRATHS KAREN M
权利人:PURDUE RESEARCH FOUNDATION
摘要:There is described a biocatalytic method for the synthesis of cathecol from a renewable source such as glucose. The method comprises inducing a divergent pathway in the shikimate pathway of a host cell. Additionally, there are described methods for making precursors to cathecol such as protocatechuate.

专利号:WO-2008150031-A1
优先权日:2007-06-08
标题:Inhibitor of biosynthesis of plant hormone auxin, chemical plant regulator comprising the inhibitor as active ingredient, herbicidal agent, and use thereof
发明人:SHIMADA YUKIHISA; GODA HIDEKI; TACHIKAWA TOMOE; ISHII TAKAHIRO; SOENO KAZUO; FUJIOKA SHOZO; ASAMI TADAO
权利人:RIKEN; SHIMADA YUKIHISA; GODA HIDEKI; TACHIKAWA TOMOE; ISHII TAKAHIRO; SOENO KAZUO; FUJIOKA SHOZO; ASAMI TADAO
摘要:The first object is to provide an inhibitor of the synthesis of endogenous auxin. The second object is to provide a plant growth inhibitor or a herbicidal agent utilizing the auxin biosynthesis inhibitor. Thus, disclosed are: a method for screening a candidate for an auxin biosynthesis inhibitor capable of inhibiting the expression of an auxin-inducible gene, by adding each of candidate compounds for the auxin inhibitor to a plant; a method for selecting a compound capable of actually inhibiting the auxin synthesis in a plant, by adding each of candidate compounds to the plant, disrupting the plant and then measuring the amount of endogenous auxin; and a method for selecting a compound capable of inhibiting the production of indolpyruvic acid in the presence of a tryptophan deaminase and tryptophan which are prepared in advance. More specifically disclosed are: an auxin biosynthesis inhibitor comprising AVG, AOA, AOIBA, L-AOPP or an analogue thereof; and a plant growth regulator or a herbicidal agent comprising the compound as an active ingredient.

专利号:US-2021002677-A1
优先权日:2015-04-16
标 题:Synthesis of omega functionalized products
发明人:GONZALEZ RAMON; CHEONG SEOKJUNG; CLOMBURG JAMES M
权利人:GONZALEZ RAMON
摘要:The use of microorganisms to make omega- and/or omega-1-functionalized products through an iterative carbon chain elongation pathway that we call a reverse beta oxidation pathway. The pathway uses omega-functionalized CoA thioesters as primers and acetyl-CoA as the extender unit in a non-decarboxylative Claisen condensation, and then uses beta oxidation or fatty acid synthesis enzymes to complete the cycle, via reductase, dehydratase and reductase reactions. Various termination enzymes that act on the functionalized beta-keto acyl-CoA intermediates of the pathway and produce omega or omega-1 functionalized products. The action of termination enzymes on such intermediates yield a large variety of products.

专利号:US-2018135059-A1
优先权日:2015-04-16
标题 :Synthesis of omega functionalized products
发明人:GONZALEZ RAMON; CHEONG SEOKJUNG; CLOMBURG JAMES M
权利人:UNIV RICE WILLIAM M
摘要:The use of microorganisms to make omega- and/or omega-l-functionalized products through an iterative carbon chain elongation pathway that we call a reverse beta oxidation pathway. The pathway uses omega-functionalized CoA thioesters as primers and acetyl-CoA as the extender unit in a non-decarboxylative Claisen condensation, and then uses beta oxidation or fatty acid synthesis enzymes to complete the cycle, via reductase, dehydratase and reductase reactions. Various termination enzymes that act on the functionalized beta-keto acyl-CoA intermediates of the pathway and produce omega or omega-1 functionalized products. The action of termination enzymes on such intermediates yield a large variety of products.
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合成参考文献


参考文献:10.1007/s10886-011-9991-7
摘要:Abreu IN, Ahnlund M, Moritz T, Albrectsen BR. UHPLC-ESI/TOFMS Determination of Salicylate-like Phenolic Gycosides in Populus tremula Leaves. Journal of Chemical Ecology. 2011 Jul 06;37(8):857. doi: 10.1007/s10886-011-9991-7.
参考文献:10.1186/1471-2091-12-36
摘要:Kenyon CP, Steyn A, Roth RL, Steenkamp PA, Nkosi TC, Oldfield LC. The role of the C8 proton of ATP in the regulation of phosphoryl transfer within kinases and synthetases. BMC Molecular and Cell Biology. 2011 Jul 13;12(1):36. doi: 10.1186/1471-2091-12-36.
参考文献:10.1021/bi200599j
摘要:Olucha J, Ouellette AN, Luo Q, Lamb AL. pH Dependence of catalysis by Pseudomonas aeruginosa isochorismate-pyruvate lyase: implications for transition state stabilization and the role of lysine 42. Biochemistry. 2011 Aug 23;50(33):7198–207.
参考文献:10.1371/journal.ppat.0010031
摘要:Zhang S, Chen Y, Potvin E, Sanschagrin F, Levesque RC, McCormack FX, Lau GW. Comparative Signature-Tagged Mutagenesis Identifies Pseudomonas Factors Conferring Resistance to the Pulmonary Collectin SP-A. PLoS Pathog. 2005 Nov 25;1(3):e31. doi: 10.1371/journal.ppat.0010031.
参考文献:10.1111/j.1472-765x.2011.03126.x
摘要:Xiao J, Chen T, Wang Q, Liu Q, Wang X, Lv Y, Wu H, Zhang Y. Search for live attenuated vaccine candidate against edwardsiellosis by mutating virulence-related genes of fish pathogen Edwardsiella tarda. Lett Appl Microbiol. 2011 Oct;53(4):430–7. doi: 10.1111/j.1472-765x.2011.03126.x.
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