(2R,3S)-2,3-dihydroxy-3-methylpentanoic acid

• 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,3S)-2,3-dihydroxy-3-methylpentanoic acid
• 英文别名: (2R,3S)-2,3-dihydroxy-3-methylpetanoic acid；(2R,3S)-(-)-2,3-Dihydroxy-3-methylpentansaeure
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PDGXJDXVGMHUIR-NJGYIYPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  10
• 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：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-ethyl-3-methyl-oxiranecarboxylic acid ethyl ester 在 barium dihydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 (2R,3S)-2,3-dihydroxy-3-methylpentanoic acid
  参考文献：
  名称：

  Continuing Studies on the Cyanobacterium Lyngbya sp.: Isolation and Structure Determination of 15-Norlyngbyapeptin A and Lyngbyabellin D

  摘要：

  Re-collections of the cyanobacterium Lyngbya sp. have yielded two more members of the lyngbyapeptin and lyngbyabellin families. The gross structures of 15-norlyngbyapeptin A (1) and lyngbyabellin D (3) were deduced through standard 2D NMR techniques, with the absolute configuration of both elucidated through degradation and comparison with commercially available and synthetic standards. Degradation to the a-amino acid and NOE correlations determined the absolute and relative configuration of the 4-amino-3-hydroxy-5-methylhexanoic acid unit in 3. Lyngbyabellin D (3) displayed an IC50 value of 0.1 mM against the KB cell line.

  DOI：

  10.1021/np030011g

文献信息

• Cytotoxic Halogenated Macrolides and Modified Peptides from the Apratoxin-Producing Marine Cyanobacterium <i>Lyngbya bouillonii</i> from Guam
  作者：Susan Matthew、Lilibeth A. Salvador、Peter J. Schupp、Valerie J. Paul、Hendrik Luesch

  DOI：10.1021/np1004032

  日期：2010.9.24

  27-deoxylyngbyabellin A (4) and lyngbyabellin J (5), a novel macrolide of the laingolide family, laingolide B (6), and a linear modified peptide, lyngbyapeptin D (7), along with known lyngbyabellins A and B, lyngbyapeptin A, and lyngbyaloside. The structures of 1−7 were elucidated by a combination of NMR spectroscopic and mass spectrometric analysis. Compounds 1−6 were either brominated (1−3) or chlorinated (4−6)

  来自关岛阿普拉港浅滩礁的海洋蓝藻Lyngbya bouillonii 的收集提供了三种迄今为止未描述的糖苷大环内酯 lyngbyaloside 类似物，即 2- epi- lyngbyaloside ( 1 ) 和区域异构体 18 E - 和 18 Z- lyngbyalosides （2和3）。同时，我们发现了破坏细胞骨架肌动蛋白的 lyngbyabellins 的两种新类似物，27-脱氧林比林 A ( 4 ) 和 林比林 J ( 5 )，莱戈内酯家族的一种新型大环内酯，林戈内酯 B ( 6 ) 和线性修饰肽 D lyngbyap ( 7)，以及已知的 lyngbyabellins A 和 B、lyngbyapeptin A 和 lyngbyaloside。的结构1 - 7通过NMR光谱和质谱分析的组合阐明。化合物1 - 6被溴化 ( 1 - 3 ) 或氯化 ( 4 - 6 )，这与卤化是许多海洋天然产物的标志一致。由于存在
• Absolute configuration of 2,3-dihydroxy-3-methylpentanoic acid, an intermediate in the biosynthesis of isoleucine
  作者：D. H. G. Crout、D. Whitehouse

  DOI：10.1039/c39720000398

  日期：——

  The dihydroxy-acid precursor (VII) of isoleucine (IX) is shown to have the 2R,3R-configuration.

  异亮氨酸（IX）的二羟基酸前体（VII）显示具有2 R，3 R-构型。
• Synthetic Studies on Pyridomycin. III. Chiral Synthesis of (2<i>R</i>,2<i>S</i>)-(−)-2,3-Dihydroxy-3-methylpentanoic Acid from Sugar Derivative
  作者：Mitsuhiro Kinoshita、Hiroshi Hamazaki、Masaki Awamura

  DOI：10.1246/bcsj.51.3595

  日期：1978.12

  successive 3,4-O-isopropylidenation, debenzoylation, hydrogenolysis, and two-stage oxidation with periodate-hypoiodite afforded (4R,5S)-(+)-5-ethyl-2,2,5-trimethyl-1,3-dioxolane-4-carboxylic acid (15) in 24.6% overall yield from 5. Hydrolysis of 15 gave (2R,3S)-(−)-2,3-dihydroxy-3-methylpentanoic acid. The acetonide 15 is usefull as a synthon for pyridomycin synthesis.

  3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose (5) 与乙基溴化镁的格氏反应生成 3-O-benzyl-6-deoxy- 5-C-乙基-1,2-O-异亚丙基-α-D-呋喃葡萄糖 (6) 作为主要产物，立体选择性为 91%。6 的水解，然后是连续的高碘酸盐氧化和氢化铝锂还原，得到 2-O-benzyl-5-deoxy-4-C-ethyl-D-arabinitol。9 的选择性苯甲酰化，然后依次进行 3,4-O-异亚丙基化、脱苯甲酰化、氢解和高碘酸盐-次碘酸盐的两阶段氧化，得到 (4R,5S)-(+)-5-乙基-2,2,5-三甲基-1,3-二氧戊环-4-羧酸(15)，来自5的总产率为24.6%。15的水解得到(2R,3S)-(-)-2,3-二羟基-3-甲基戊酸。丙酮化物 15 可用作吡啶霉素合成的合成子。
• Crout; Whitehouse, Journal of the Chemical Society. Perkin transactions I, 1977, # 5, p. 544 - 549
  作者：Crout、Whitehouse

  DOI：——

  日期：——
• Continuing Studies on the Cyanobacterium <i>Lyngbya </i>sp.: Isolation and Structure Determination of 15-Norlyngbyapeptin A and Lyngbyabellin D
  作者：Philip G. Williams、Hendrik Luesch、Wesley Y. Yoshida、Richard E. Moore、Valerie J. Paul

  DOI：10.1021/np030011g

  日期：2003.5.1

  Re-collections of the cyanobacterium Lyngbya sp. have yielded two more members of the lyngbyapeptin and lyngbyabellin families. The gross structures of 15-norlyngbyapeptin A (1) and lyngbyabellin D (3) were deduced through standard 2D NMR techniques, with the absolute configuration of both elucidated through degradation and comparison with commercially available and synthetic standards. Degradation to the a-amino acid and NOE correlations determined the absolute and relative configuration of the 4-amino-3-hydroxy-5-methylhexanoic acid unit in 3. Lyngbyabellin D (3) displayed an IC50 value of 0.1 mM against the KB cell line.