(2S,3R,4S)-3,4-二羟基吡咯烷-2-羧酸 | 95341-64-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2S,3R,4S)-3,4-二羟基吡咯烷-2-羧酸
• 英文名称: (2S,3R,4S)-3,4-dihydroxypyrrolidine-2-carboxylic acid
• 英文别名: L-2,3-trans-3,4-cis-3,4-dihydroxy-proline；L-2,3-trans-3,4-cis-dihydroxyproline；(2S,3R,4S)-3,4-dihydroxy-L-proline；trans-2,3-cis-3,4-dihydroxyproline；(2S,3R,4S)-3,4-dihydroxy-proline；(2R,3R,4S)-3,4-dihydroxyproline
• CAS: 95341-64-3
• 化学式: C₅H₉NO₄
• 分子量: 147.131
• InChiKey: HWNGLKPRXKKTPK-HZLVTQRSSA-N

物化性质

• 沸点：
  411.5±45.0 °C(Predicted)
• 密度：
  1.617±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  89.8
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3:5,6-di-O-isopropylidene-D-gulitol 在 4-二甲氨基吡啶 、 palladium on activated charcoal sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、 氢气 、 溶剂黄146 、 三氟乙酸 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 137.67h， 生成 (2S,3R,4S)-3,4-二羟基吡咯烷-2-羧酸
  参考文献：
  名称：

  Polyhydroxylated pyrrolidines from sugar lactomes: Synthesis of 1,4-dideoxy-1,4-imino-d-glucitol from d-galactonolactone and syntheses of 1,4-dideoxy-1,4-imino-d-allitol, 1,4-dideoxy-1,4-imino-d-ribitol, and (2s,3r,4s)-3,4-dihydroxyproline from d-gulonolactone

  摘要：

  DOI：

  10.1016/s0040-4020(01)81716-6

文献信息

• Studies on the selectivity of proline hydroxylases reveal new substrates including bicycles
  作者：Tristan J. Smart、Refaat B. Hamed、Timothy D.W. Claridge、Christopher J. Schofield

  DOI：10.1016/j.bioorg.2019.103386

  日期：2020.1

  Studies on the substrate selectivity of recombinant ferrous-iron- and 2-oxoglutarate-dependent proline hydroxylases (PHs) reveal that they can catalyse the production of dihydroxylated 5-, 6-, and 7-membered ring products, and can accept bicyclic substrates. Ring-substituted substrate analogues (such hydroxylated and fluorinated prolines) are accepted in some cases. The results highlight the considerable

  对依赖于铁-铁和2-氧戊二酸酯的脯氨酸羟化酶重组酶的底物选择性的研究表明，它们可以催化二羟基化的5、6和7元环产物的产生，并且可以接受双环底物。在某些情况下，可以接受环取代的底物类似物（例如羟基化和氟化的脯氨酸）。结果突出了在生物催化中氨基酸羟化酶和其他2OG加氧酶的巨大潜力，但尚未充分开发。
• (�)-4-Amino-4,5-dideoxyribose, (�)-4-amino-4-deoxyerythrose, and (�)-dihydroxyproline derivatives fromN-dienyl-?-lactams
  作者：Jean-Bernard Behr、Albert Defoin、Naheed Mahmood、Jacques Streith

  DOI：10.1002/hlca.19950780510

  日期：1995.8.9

  Deprotection and saponification of the latter led to aminodeoxyerythrose and to aminodeoxyribose derivatives as an equilibrium of pyrrolidinose equivalents, i.e., hemiaminals 14a, b, imines 14′a, b, and dimers 14″a,b, respectively (Scheme 3). Hydrocyanic acid addition to 11a, b led ultimately to the proline derivatives 16a, b (Scheme 2). Compound 11b proved to be an inhibitor of syncytium formation in AIDS-infected

  酰基亚硝基亲二烯体4与N-（丁二烯基）吡咯烷酮衍生物2a，b的杂二狄尔斯-阿尔德环加成反应对恶嗪加合物5a，b具有完全的区域选择性（方案1）。顺序的渗透作用，对随后的二醇的保护以及NO键的还原给出了预期的半胱氨酸盐11a，b，其特征在于它们的结晶亚硫酸盐加合物12a，b（方案1和2））。后者的脱保护和皂化导致氨基脱氧赤藓糖和氨基脱氧核糖衍生物作为吡咯烷糖当量的平衡，即分别为半缩醛14a，b，亚胺14′a，b和二聚体14″ a，b（方案3）。向11a，b中添加氢氰酸最终导致脯氨酸衍生物16a，b（方案2）。化合物11b被证明是艾滋病感染细胞中合胞体形成的抑制剂。
• Diversity oriented concise asymmetric synthesis of azasugars: a facile access to l -2,3- trans -3,4- cis -dihydroxyproline and (3 S ,5 S )-3,4,5-trihydroxypiperidine
  作者：Vikas S. Gajare、Sandip R. Khobare、Rajender Datrika、K. Srinivas Reddy、Nagaraju Rajana、Sarvesh Kumar、B. Venkateswara Rao、U.K. Syam Kumar

  DOI：10.1016/j.tetlet.2015.10.013

  日期：2015.12

  Diversity oriented concise asymmetric syntheses of l-2,3-trans-3,4-cis-dihydroxyproline and (3S,5S)-3,4,5-trihydroxypiperidine have been developed from (R)-glycidol. The key step of the synthesis is Sharpless asymmetric dihydroxylation on enantiomerically pure TBDMS protected allylic alcohol 14 which generates the triol intermediate 15 in excellent de. The (2R,3R,4S)-2,3-dihydroxypentanoate derivative

  多样性导向简洁的不对称合成升-2,3-反式-3,4-顺-dihydroxyproline和（3小号，5小号）-3,4,5- trihydroxypiperidine已从（显影- [R ）-缩水甘油。合成的关键步骤是在受保护的烯丙基醇对映体纯TBDMS Sharpless不对称二羟基化14，其生成三醇中间体15在良好的去。（2 R，3 R，4 S）-2,3-二羟基戊酸酯衍生物15随后转化为天然吡咯烷氮杂糖1和非天然哌啶氮杂糖4在级联反应条件下产率较高。
• Discovery of New Fe(II)/α-Ketoglutarate-Dependent Dioxygenases for Oxidation of <scp>l</scp>-Proline
  作者：Erika Tassano、Charles Moore、Solene Dussauge、Alexandra Vargas、Radka Snajdrova

  DOI：10.1021/acs.oprd.1c00405

  日期：2022.7.15

  clustering of proteins, we predicted regio- and stereoselectivity in the hydroxylation reaction and validated this hypothesis experimentally. Two novel byproducts in the reactions with enzymes from Bacillus cereus and Streptomyces sp. were isolated, and the structures were determined to be a 3,4-epoxide and a 3,4-diol, respectively. The mechanism for the formation of the epoxide was investigated by performing

  报道了新型 Fe(II)/α-酮戊二酸依赖性双加氧酶 (αKGDs) 的基因组挖掘，以扩展l-脯氨酸氧化中的酶谱。通过蛋白质的聚类，我们预测了羟基化反应中的区域选择性和立体选择性，并通过实验验证了这一假设。与蜡状芽孢杆菌和链霉菌酶反应的两种新副产物。被分离，结构分别被确定为3,4-环氧化物和3,4-二醇。通过进行18 O-标记实验来研究环氧化物的形成机理。我们建议该机制通过初始顺式进行-3-羟基化然后闭环。对亚克数量的起始材料进行生物催化步骤，而没有对条件进行任何显着优化。然而，底物浓度比通常报道的重组 P450 介导的羟基化效价高 40 倍，表明 αKGD 在制备规模上的合成潜力。
• Stereoselective Synthesis of (+)-1,8-Di-epi- and (-)-1-epi-Swainsonine from an (S)-Pyroglutamic Acid Derivative.
  作者：Nobuo IKOTA

  DOI：10.1248/cpb.41.1717

  日期：——

  (+)-1, 8-Di-epi-swainsonine (15) and (-)-1-epi-swainsonine (17) were synthesized stereoselectively from an (S)-pyroglutamic acid derivative (1a). A (2R, 3R, 4R)-3, 4-dihydroxy-2-hydroxymethylpyrrolidine derivative (6a) was prepared by cis-dihydroxylation of an α, β-unsaturated lactam (2) followed by epimerization of the di-O-benzyl derivative (3b) as the key reactions. The diastereoselective allylation of the aldehyde 6b obtained from 6a and subsequent cyclization of 13 and 16 gave 15 and 17, respectively. It proved that 1, 8-di-epi-swainsonine (15) is dextrorotatory.

  由(S)-焦谷氨酸衍生物(1a)立体选择性合成(+)-1, 8-二-表-苦马豆素(15)和(-)-1-表-苦马豆素(17)。 (2R, 3R, 4R)-3, 4-二羟基-2-羟甲基吡咯烷衍生物 (6a) 通过 α, β-不饱和内酰胺 (2) 的顺式二羟基化和二-O-苄基衍生物的差向异构化制备(3b)为关键反应。由6a获得的醛6b的非对映选择性烯丙基化以及随后13和16的环化分别得到15和17。证明1, 8-二-表-苦豆素(15)具有右旋性。