3-cyclohexyl-3-hydroxypropanoic acid | 4354-62-5

• 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-cyclohexyl-3-hydroxypropanoic acid
• 英文别名: 3-hydroxy-3-cyclohexylpropionic acid；β-Cyclohexyl-β-hydroxypropionsaeure
• CAS: 4354-62-5
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: LXMZSQUIERKWQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-3-hydroxypropanoic acid 在 4-二甲氨基吡啶 、 Streptomyces sp. HK-803 phoslactomycin polyketide synthase module 1 ketoreductase domain 、 三羟甲基氨基甲烷盐酸盐 、 三(2-羰基乙基)磷盐酸盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 甘油 、 pyridinium chlorochromate 、 还原型辅酶II(NADPH)四钠盐 、 sodium chloride 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structural and Stereochemical Analysis of a Modular Polyketide Synthase Ketoreductase Domain Required for the Generation of a cis-Alkene

  摘要：

  The formation of an activated cis-3-cyclohexylpropenoic acid by Plm1, the first extension module of the phoslactomycin polyketide synthase, is proposed to occur through an L-3-hydroxyacyl-intermediate as a result of ketoreduction by an A-type ketoreductase (KR). Here, we demonstrate that the KR domain of Plm1 (PlmKR1) catalyzes the formation of an L-3-hydroxyacyl product. The crystal structure of PlmKR1 revealed a well-ordered active site with a nearby Trp residue characteristic of A-type KRs. Structural comparison of PlmKR1 with B-type KRs that produce D-3-hydroxyacyl intermediates revealed significant differences. The active site of cofactor-bound A-type KRs is in a catalysis-ready state, whereas cofactor-bound B-type KRs are in a precatalytic state. Furthermore, the closed lid loop in substrate-bound A-type KRs restricts active site access from all but one direction, which is proposed to control the stereochemistry of ketoreduction.

  DOI：

  10.1016/j.chembiol.2013.04.014
• 作为产物：
  描述：

  (+/-)-methyl 3-(cyclohexyl)-3-hydroxypropanoate 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 3-cyclohexyl-3-hydroxypropanoic acid
  参考文献：
  名称：

  Structural and Stereochemical Analysis of a Modular Polyketide Synthase Ketoreductase Domain Required for the Generation of a cis-Alkene

  摘要：

  The formation of an activated cis-3-cyclohexylpropenoic acid by Plm1, the first extension module of the phoslactomycin polyketide synthase, is proposed to occur through an L-3-hydroxyacyl-intermediate as a result of ketoreduction by an A-type ketoreductase (KR). Here, we demonstrate that the KR domain of Plm1 (PlmKR1) catalyzes the formation of an L-3-hydroxyacyl product. The crystal structure of PlmKR1 revealed a well-ordered active site with a nearby Trp residue characteristic of A-type KRs. Structural comparison of PlmKR1 with B-type KRs that produce D-3-hydroxyacyl intermediates revealed significant differences. The active site of cofactor-bound A-type KRs is in a catalysis-ready state, whereas cofactor-bound B-type KRs are in a precatalytic state. Furthermore, the closed lid loop in substrate-bound A-type KRs restricts active site access from all but one direction, which is proposed to control the stereochemistry of ketoreduction.

  DOI：

  10.1016/j.chembiol.2013.04.014

文献信息

• Selective transformation of nitriles into amides and carboxylic acids by an immobilized nitrilase
  作者：Norbert Klempier、Anna de Raadt、Kurt Faber、Herfried Griengl

  DOI：10.1016/s0040-4039(00)92623-6

  日期：1991.1

  Using an immobilized nitrilase from Rhodococcus sp. mild and selective hydrolysis of nitriles can be achieved even in the presence of acid or base sensitive groups under neutral conditions. This method is applicable to a broad range of substrates as exemplified by aliphatic, alicyclic, heterocyclic and carbohydrate type nitriles.

  使用来自红球菌属的固定化腈水解酶。即使在中性条件下存在酸或碱敏感基团，也可以实现腈的温和选择性水解。该方法适用于各种底物，例如脂族，脂环族，杂环和碳水化合物类腈。
• Aldol-type Reactions of Unmasked Iodoacetic Acid with Carbonyl Compounds Promoted by Samarium Diiodide:  Efficient Synthesis of Carboxylic 3-Hydroxyacids and Their Derivatives
  作者：José M. Concellón、Carmen Concellón

  DOI：10.1021/jo060118j

  日期：2006.6.1

  An easy, direct, general, and efficient samarium diiodide-mediated preparation of 3-hydroxyacids 1 in high yield by reaction of different aldehydes or ketones with commercially available iodoacetic acid is described. The application of different esterification procedures to the crude 3-hydroxyacids so obtained afforded the corresponding 3-hydroxyesters. Also, the cyclization of crude 3-hydroxycarboxylic

  本发明描述了一种简单，直接，通用和有效的由二碘化mar介导的3-羟基酸1的制备方法，该方法通过使不同的醛或酮与市售碘乙酸反应而以高收率进行制备。对如此获得的粗3-羟基酸应用不同的酯化方法，得到相应的3-羟基酯。同样，粗制的3-羟基羧酸的环化允许制备β-内酯。提出了一种机制来解释3-羟基酸1的合成。
• The reaction of trialkylvinylborate with carbon dioxide. A new method for the preparation of β-hydroxycarboxylic acids from alkenes
  作者：Min-Zhi Deng、Ding-An Lu、Wei-Hua Xu

  DOI：10.1039/c39850001478

  日期：——

  Chloromagnesium trialkylvinylborate, (R3BCHCH2)MgCl, on reaction with carbon dioxide under pressure, followed by oxidation with alkaline hydrogen peroxide, gives a β-hydroxycarboxylic acid.

  三烷基乙烯基硼酸氯镁（R 3 BCH CH 2）MgCl，在压力下与二氧化碳反应，然后用碱性过氧化氢氧化，得到β-羟基羧酸。
• Resolution and asymmetric synthesis of 3-hydroxycarboxylic acids by using (–)-menthone as a chiral template
  作者：Toshiro Harada、Tetsuya Yoshida、Yasuhiro Kagamihara、Akira Oku

  DOI：10.1039/c39930001367

  日期：——

  1,3-Dioxan-4-ones 6and 7 derived from (–)-menthone can be utilized in resolution of 3-hydroxycarboxylic acids and asymmetric synthesis of 2-substituted 3-hydroxycarboxylic acids.

  衍生自（-）-薄荷酮的1,3-二恶烷-4-酮6和7可用于拆分3-羟基羧酸和2-取代的3-羟基羧酸的不对称合成。
• [EN] INHIBITORS OF CRUZIPAIN AND OTHER CYSTEINE PROTEASES<br/>[FR] INHIBITEURS DE LA CRUZIPAINE ET AUTRES CYSTEINES PROTEASES
  申请人：INCENTA LTD

  公开号：WO2002057270A1

  公开（公告）日：2002-07-25

  Compounds of general formula (I) or general formula (II) wherein R1, P1, P2, Q, Y, (X)o, (W)n, (V)m, Z and U are as defined in the specification, are inhibitors of cruzipain and other cysteine protease inhibitors and are useful as therapeutic agents, for example in Chagas' disease, or for validating therapeutic target compounds.

  通式(I)或通式(II)的化合物，在规范中定义的R1，P1，P2，Q，Y，(X)o，(W)n，(V)m，Z和U，是cruzipain和其他半胱氨酸蛋白酶抑制剂的抑制剂，并且可用作治疗剂，例如在恶性贫血病中，或用于验证治疗靶点化合物。