(2R,3R)-2-methyl-3-hydroxypentanoic acid | 109215-41-0

• 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: (2R,3R)-2-methyl-3-hydroxypentanoic acid
• 英文别名: (2R,3R)-3-hydroxy-2-methylpentanoic acid
• CAS: 109215-41-0
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: NVIHALDXJWGLFD-RFZPGFLSSA-N

物化性质

• 沸点：
  250.5±23.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2R,3R)-2-methyl-3-hydroxypentanoic acid 、 辅酶 A 在 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以4 mg的产率得到(2R,3R)-2-methyl-3-hydroxypentanoyl-CoA
  参考文献：
  名称：

  Stereospecificity of the Dehydratase Domain of the Erythromycin Polyketide Synthase

  摘要：

  The dehydratase (DH) domain of module 4 of the 6-deoxyerythronolide B synthase (DEBS) has been shown to catalyze an exclusive syn elimination/syn addition of water. Incubation of recombinant DH4 with chemoenzymatically prepared anti-(2R,3R)-2-methyl-3-hydroxypentanoyl-ACP (2a-ACP) gave the dehydration product 3-ACP. Similarly, incubation of DH4 with synthetic 3-ACP resulted in the reverse enzyme-catalyzed hydration reaction, giving an similar to 3:1 equilbrium mixture of 2a-ACP and 3-ACP. Incubation of a mixture of propionyl-SNAC (4), methylmalonyl-CoA, and NADPH with the DEBS beta-ketoacyl synthase-acyl transferase [KS6][AT6] dido-main, DEBS ACP6, and the ketoreductase domain from tylactone synthase module 1 (TYLS KR1) generated in situ anti-2a-ACP that underwent DH4-catalyzed syn dehydration to give 3-ACP. DH4 did not dehydrate syn-(2S,3R)-2b-ACP, syn-(2R,3S)-2c-ACP, or anti-(2S,3S)-2d-ACP generated in situ by DEBS KR1, DEBS KR6, or the rifamycin synthase KR7 (RIFS KR7), respectively. Similarly, incubation of a mixture of (2S,3R)-2-methyl-3-hydroxypentanoyl-N-acetylcysteaminethioester (2b-SNAC), methylmalonyl-CoA, and NADPH with DEBS [KS6][AT6], DEBS ACP6, and TYLS KR1 gave anti-(2R,3R)6-ACP that underwent syn dehydration catalyzed by DEBS DH4 to give (4R,5R)-(E)-2,4-dimethyl-5-hydroxy-hept-2-enoyl-ACP (7-ACP). The structure and stereochemistry of 7 were established by GC-MS and LC-MS comparison of the derived methyl ester 7-Me to a synthetic sample of 7-Me.

  DOI：

  10.1021/ja107344h
• 作为产物：
  描述：

  [(1R,2S)-2-[methyl(1,2,3,4,5,6,7,8-octahydroanthracen-9-ylsulfonyl)amino]-1-phenylpropyl] (2R,3R)-3-hydroxy-2-methylpentanoate 生成 (2R,3R)-2-methyl-3-hydroxypentanoic acid
  参考文献：
  名称：

  的程度顺式-选择性为羧酸酯的硼介导的不对称醛醇缩合反应

  摘要：

  为顺式选择性羟醛缩合反应的新的手性试剂已经被开发了基于最近的发现，即羧酸酯的硼介导的醛醇缩合反应的立体化学通过该酯的醇部分的膨松度的控制，通过适当选择试剂，并受烯醇化条件的影响。这种易于获得的廉价试剂已被用于大环内酯单萜内酯的合成研究中。

  DOI：

  10.1016/s0040-4039(98)00123-3

文献信息

• Asymmetric and ?anti?-Selective Aldolisations of Acetates and Propionates. Preliminary Communication
  作者：Wolfgang Oppolzer、Jos� Marco-Contelles

  DOI：10.1002/hlca.19860690725

  日期：1986.10.29

  Starting from acetates 1 and propionates 6, TiCl4-mediated addition of their silyketene acetals 2 and 7 to aldehydes gave aldols 4 and 9, respectively, with high π-face and ‘anti’ differentiation (Schemes, and Tables 1 and 2). Alternation of the (E/Z)-enolate geometry led to reversed α- and β-inductions (7 9b, 8 10b). Non-destructive removal of the auxiliary yielded enantiomerically pure β -hydroxycarboxylic

  从乙酸盐1和丙酸酯6开始，TiCl 4介导的将它们的硅酮烯醇缩醛2和7加到醛中，分别得到具有高π面和'抗'区分性的醇醛4和9（方案，以及表1和表2）。（E / Z）烯醇几何形状的交替导致相反的α和β诱导（7 9b，8 10b）。非破坏性去除辅助生成的对映体纯的β-羟基羧酸13 。
• The Thioesterase of the Erythromycin-Producing Polyketide Synthase: Influence of Acyl Chain Structure on the Mode of Release of Substrate Analogues from the Acyl Enzyme Intermediates
  作者：Kira J. Weissman、Cameron J. Smith、Ulf Hanefeld、Ranjana Aggarwal、Matthew Bycroft、James Staunton、Peter F. Leadlay

  DOI：10.1002/(sici)1521-3773(19980605)37:10<1437::aid-anie1437>3.0.co;2-7

  日期：1998.6.5

  synthase (PKS) have demonstrated that the ability of this enzyme to act as a universal decoupler is limited, but stereochemical variation is readily tolerated. Synthetic analogues with all four stereochemical configurations of the natural substrate's 2-methyl-3-hydroxy substitution pattern (1-4; X=p-nitrophenoxy) were substrates for the enzyme.

  基因工程化的聚酮化合物的生产主要取决于硫酯酶的活性以释放产品。用来自红霉素聚酮化合物合酶（PKS）的硫酯酶进行的体外研究表明，该酶用作通用解偶联剂的能力有限，但很容易耐受立体化学变异。具有天然底物的2-甲基-3-羟基取代模式（1-4； X =对硝基苯氧基）的所有四个立体化学构型的合成类似物是该酶的底物。
• Compounds for Use in Therapy
  申请人：Baird Mark Stephen

  公开号：US20110150981A1

  公开（公告）日：2011-06-23

  A compound of formula (I) for use in the treatment of a disease of the immune system; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R 1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R 2 , Wand R 4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkenylene, arylene, alkylarylene, cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester and thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C-OR 5 ; wherein R 5 is alkyl or haloalkyl, and A is O, S or Me, wherein R 6 may be H or 20 alkyl.

  化合物式（I）的化合物用于治疗免疫系统疾病；其中R是具有1至50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R1是具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；R2，W和R4中的每一个都独立地选择自具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团的取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团；X，Y和Z中的每一个都独立地选择自可选取代的烷基，烯基，烯基，芳基，烷基芳基，环烷基，酮，酯，酰胺，亚酰胺，亚胺，硫醚，醚，硫酯和硫酮的基团；P从氢，烷基，糖残基或金属，膦，铵或铵物种中选择；其中X，Y和Z中至少有一个包括从环丙基，C = A，C-AH和C-OR5中选择的基团；其中R5是烷基或卤代烷基，A是O，S或Me，R6可能是H或20烷基。
• Adjuvants for Use in Vaccination
  申请人：Baird Mark Stephen

  公开号：US20110142916A1

  公开（公告）日：2011-06-16

  A compound of formula (I) for use as an adjuvant in vaccination; wherein R is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 50 carbon atoms; R 1 is an optionally-substituted alkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl moiety having from 1 to 40 carbon atoms; each of R 2 , R 3 and R 4 is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, arylalkylene or alkylarylene moiety having from 1 to 40 carbon atoms; each of X, Y and Z is independently selected from an optionally-substituted alkylene, alkenylene, alkynylene, arylene, alkylarylene or cycloalkylene, ketone, ester, amide, imide, imine, thioether, ether, thioester, thioketone; and P is selected from hydrogen, an alkyl group, a sugar residue, or a metal, phosphonium or ammonium species; wherein at least one of X, Y and Z includes a moiety selected from cyclopropyl, C=A, C-AH and C—OR 5 ; wherein R 5 is alkyl or haloalkyl, and A is S, O or NR 6 , wherein R 6 maybe H or 20 alkyl.

  化合物式（I）的复合物用作疫苗佐剂；其中R是具有1至50个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; R1是具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; R2，R3和R4中的每一个都是独立选择的，具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，芳基烷基或烷基芳基基团; X，Y和Z中的每一个都是独立选择的，具有1至40个碳原子的可选取代的烷基，烯基，炔基，芳基，烷基芳基或环烷基，酮，酯，酰胺，亚酰胺，亚胺，硫醚，醚，硫酯，硫酮; P是氢，烷基，糖残基或金属，膦或铵物种中的一种；其中X，Y和Z中至少一个包括从环丙基，C=A，C-AH和C—OR5中选择的基团; 其中R5是烷基或卤代烷基，A是S，O或NR6，其中R6可以是H或20烷基。
• Assessing the Balance between Protein−Protein Interactions and Enzyme−Substrate Interactions in the Channeling of Intermediates between Polyketide Synthase Modules
  作者：Nicholas Wu、Stuart Y. Tsuji、David E. Cane、Chaitan Khosla

  DOI：10.1021/ja010219t

  日期：2001.7.1

  reassess the steady-state kinetic parameters of individual DEBS modules when primed in a more "natural" channeling mode by the same panel of diketide substrates used earlier. Here we describe these assays and use them to quantify the kinetic benefit of linker-mediated substrate channeling in a modular PKS. This benefit can be substantial, especially for intrinsically poor substrates. Examples are presented

  6-Deoxyerythronolide B 合酶 (DEBS) 是模块化聚酮化合物合酶 (PKS)，可催化 6-deoxyerythronolide B (6-dEB)（抗生素红霉素的苷元前体）的生物合成。6-dEB 的生物合成证明了该多功能酶家族非凡的底物选择性和立体选择性。矛盾的是，DEBS 已被证明是一种有吸引力的组合生物合成支架，表明其组成模块也非常耐受非天然底物。通过用一组激活为 N-乙酰半胱胺 (NAC) 硫酯的双酮化合物询问 DEBS 的单个模块，最近表明单个模块具有区分某些非对映异构双酮化合物的显着能力。然而，由于在这些研究中使用游离 NAC 硫酯作为底物，模块由扩散过程引发，这排除了共价、底物通道机制的参与，通过该机制，酶结合的中间体在多模块 PKS 中直接从一个模块转移到下一个模块。最近的证据表明蛋白质-蛋白质相互作用在底物通道机制中起关键作用，这促使我们开发新的检测方法来重新评估单个