(2S)-1-戊-4-烯酰基吡咯烷-2-羧酸 | 479640-29-4

• 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)-1-戊-4-烯酰基吡咯烷-2-羧酸
• 英文名称: N-pent-4-enoyl-L-proline
• 英文别名: N-4-pentenoyl-(S)-proline；pent-4-enoyl-L-proline；1-Pent-4-enoyl-L-proline；(2S)-1-pent-4-enoylpyrrolidine-2-carboxylic acid
• CAS: 479640-29-4
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: JHMQVIVKQGKVHG-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-1-戊-4-烯酰基吡咯烷-2-羧酸 在 lithium hydroxide 、 碘代三甲硅烷 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 生成 (S)-4-Methyl-2-{(Z)-2-[((S)-1-pent-4-enoyl-pyrrolidine-2-carbonyl)-amino]-3-phenyl-acryloylamino}-pentanoic acid methyl ester
  参考文献：
  名称：

  通过闭环易位，将脱氢苯丙氨酸衍生的小肽中的3 10螺旋结构轻松转换为环状β-turn模拟物

  摘要：

  衍生自脱氢苯丙氨酸的小肽可以以3 10螺旋结构进行预组织，该结构在闭环易位环化过程中转化为β-turn模拟物。

  DOI：

  10.1016/s0040-4039(02)01601-5
• 作为产物：
  描述：

  methyl pent-4-enoyl-L-prolinate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 生成 (2S)-1-戊-4-烯酰基吡咯烷-2-羧酸
  参考文献：
  名称：

  Development of Macrocyclic Peptides Containing Epoxyketone with Oral Availability as Proteasome Inhibitors

  摘要：

  Macrocyclization has been frequently utilized for optimizing peptide or peptidomimetic-based compounds. In an attempt to obtain potent, metabolically stable, and orally available proteasome inhibitors, 30 oprozomib-derived macrocyclic peptides with structural diversity in their N-terminus and linker were successively designed and synthesized for structure- activity relationship (SAR) studies. As a consequence, the macrocyclic peptides with N-methyl-pyrazole (24p, 24x), imidazole (24t), and pyrazole (24v) as their respective N-termini exhibited favorable in vitro activity and metabolic stability, which translated into their potent in vivo proteasome inhibitory activity after oral administration. In particular, compound 24v, as the most distinguished one among this series, displayed excellent chymotrypsin-like (ChT-L, beta 5) inhibitory potency (IC50 = 16 nM), low nanomolar antiproliferative activity against all three of the tested cell lines, and superior metabolic stability in mouse liver microsome (MLM), as well as favorable inhibition against ChT-L compared to that of oprozomib in BABL/c mice following po administration at a comparatively low dose, thereby representing a promising candidate for further development.

  DOI：

  10.1021/acs.jmedchem.8b00819

文献信息

• Repurposing the 3‐Isocyanobutanoic Acid Adenylation Enzyme SfaB for Versatile Amidation and Thioesterification
  作者：Mengyi Zhu、Lijuan Wang、Jing He

  DOI：10.1002/anie.202010042

  日期：2021.1.25

  molecules with novel skeletons, but also to identify the enzymes that catalyze diverse chemical reactions. Exploring the substrate promiscuity and catalytic mechanism of those biosynthetic enzymes facilitates the development of potential biocatalysts. SfaB is an acyl adenylate‐forming enzyme that adenylates a unique building block, 3‐isocyanobutanoic acid, in the biosynthetic pathway of the diisonitrile

  微生物天然产物的基因组挖掘使化学家不仅能够发现具有新颖骨架的生物活性分子，而且能够识别催化多种化学反应的酶。探索这些生物合成酶的底物混杂性和催化机理有助于开发潜在的生物催化剂。SfaB是一种形成酰基腺苷酸的酶，可在由硫链霉菌产生的二异腈自然产物SF2768的生物合成途径中，对独特的结构单元3-异氰基丁酸进行腺苷酸化。，并且该AMP连接酶被证明可以接受各种短链脂肪酸（SCFA）。在本文中，我们将SfaB重新用于催化那些SCFA与各种胺或硫醇亲核试剂之间的酰胺化或硫酯化反应，从而提供了另一种酶促方法来体外制备相应的酰胺和硫酯。
• Low Catalyst Loading in Ring-Closing Metathesis Reactions
  作者：Renat Kadyrov

  DOI：10.1002/chem.201202207

  日期：2013.1.14

  conversion into a broad variety of 5–16‐membered heterocyclic compounds. The practicality of this procedure was illustrated in the synthesis of 5–8‐membered N‐tert‐butoxycarbonyl (N‐Boc)‐ and N‐para‐toluenesulfonyl (N‐Ts)‐protected cyclic amines and 9–16‐membered lactones. The synthesis of macrocyclic proline‐based lactams required slightly higher catalyst loadings. Along with monocyclic products, oligomeric

  描述了一种有效的闭环复分解反应程序。在几分钟内可以达到95％的二烯丙基丙二酸二乙酯在稀溶液中的转化率，达到TOF = 4173 min -1，而载有不饱和NHC配体的商业化Ru催化剂的负载量却非常低。通常，仅需50至250 ppm的催化剂即可将近定量转化为多种5-16元杂环化合物。此过程的实用性在5-8元的合成图示ñ -叔丁氧羰基（Ñ -Boc） -和ñ -对甲苯磺酰（Ñ-Ts）保护的环胺和9-16元内酯。大环脯氨酸基内酰胺的合成需要稍高的催化剂负载量。与单环产物一起，分离并表征了寡聚副产物，主要是环二聚体。
• Synthesis of cyclic β-turn mimics from l-Pro-Phe/Phe-l-Pro derived di- and tripeptides via ring closing metathesis: the role of chirality of the Phe residue during cyclization
  作者：Biswadip Banerji、Madhushree Bhattacharya、Rajesh B Madhu、Saibal Kumar Das、Javed Iqbal

  DOI：10.1016/s0040-4039(02)01238-8

  日期：2002.9

  o-Gly-N-allyl/pent-4-enoyl-Gly-Pro-Phe-N-allyl amide derived di- and tripeptides can be cyclized leading to β-turn mimics via ring closing metathesis using Grubbs’ catalyst. The chirality of the Phe residue in these di- and tripeptides controls the cyclization during ring closing metathesis. The presence of pent-4-enoyl and allyl groups at the termini of these peptides leads to the concomitant formation

  Pent-4-enoyl-1-Pro-Phe-N-烯丙基/ pent-4-enoyl-Phe-1-Pro-N-烯丙基和pent-4-enoyl-1-Phe-Pro-Gly-N-烯丙基/戊-4-烯丙基-Gly-Pro-Phe-N-烯丙基酰胺衍生的二肽和三肽可以被环化，通过使用Grubbs的催化剂通过闭环复分解反应生成β-turn模拟物。这些二肽和三肽中Phe残基的手性控制着闭环复分解过程中的环化作用。在这些肽的末端存在戊-4-烯丙基和烯丙基会导致在环化过程中伴随着氨基酸4,5-脱氢-6-氨基己酸的形成。
• Method For Enrichment Involving Elimination By Mismatch Hybridisation
  申请人：Freskgard Per-Ola

  公开号：US20090239211A1

  公开（公告）日：2009-09-24

  The present invention relates to a method for selecting a molecule from a library of such molecules associated with identifier oligonucleotides, said molecule having affinity towards a target. The method involves contacting library with a target to allow for an interaction between the molecules and the target and partitioning a fraction enriched in identifier oligonucleotides of molecules interacting with the target. After an optional nucleic acid amplification of the partitioned fraction, the fraction is subjected to conditions at which hetero-duplexes and homo-duplexes are formed. The homo-duplexes are subsequently recovered and decoded to identify the identity of the molecule interacting with the target.
• METHOD FOR PRODUCING SECOND-GENERATION LIBRARY
  申请人：FRESKGARD Per-Ola

  公开号：US20120028812A1

  公开（公告）日：2012-02-02

  The present invention relates to a method for generating a second-generation library. In a first step, a library of encoded molecules associated with an identifier nucleic acid comprising codons identifying chemical entities that have participated in the formation of the encoded molecule is provided. In a second step, the library is partitioned and encoded molecules having a certain property are selected. Codons of identifiers of selected encoded molecules are subsequently identified, and a second-generation library is prepared using at least some of the chemical entities coded for by the identified codons. The new focussed library may be used for another partition step to select encoded molecules with a certain property.