(S)-methyl 1-butylpyrrolidine-2-carboxylate

• 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
• 英文名称: (S)-methyl 1-butylpyrrolidine-2-carboxylate
• 英文别名: methyl (2S)-1-butanoylpyrrolidine-2-carboxylate
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: YDOXTIOAUXVDHL-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-methyl 1-butylpyrrolidine-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以91%的产率得到1-(1-氧代丁基)-L-脯氨酸
  参考文献：
  名称：

  抗癌药Culicin D的Peptaibol框架的合成：AHMOD部分的立体化学分配。

  摘要：

  使用基于Fmoc的固相肽合成（SPPS）合成了有效的抗癌肽肽culicinin D的假定结构。所报告的culicinin D结构的1 H NMR数据与在AHMOD单元中C-6处的两个合成多肽融合的合成数据的比较确定了天然产物AHMOD残基的C-6立体化学为（R）。

  DOI：

  10.1021/ol302852q
• 作为产物：
  描述：

  L-脯氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 21.17h， 生成 (S)-methyl 1-butylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  抗癌药Culicin D的Peptaibol框架的合成：AHMOD部分的立体化学分配。

  摘要：

  使用基于Fmoc的固相肽合成（SPPS）合成了有效的抗癌肽肽culicinin D的假定结构。所报告的culicinin D结构的1 H NMR数据与在AHMOD单元中C-6处的两个合成多肽融合的合成数据的比较确定了天然产物AHMOD残基的C-6立体化学为（R）。

  DOI：

  10.1021/ol302852q

文献信息

• Aldehyde-based racemization in the dynamic kinetic resolution of N-heterocyclic α-amino esters using Candida antarctica lipase A
  作者：Arto Liljeblad、Anu Kiviniemi、Liisa T Kanerva

  DOI：10.1016/j.tet.2003.10.103

  日期：2004.1

  The present research introduces approaches for the dynamic kinetic resolution of the methyl esters of proline and pipecolic acid. As the result, a method was developed which is based on the acylation of the secondary amino group of the amino esters with vinyl butanoate by Candida antarctica lipase A. In the optimized method, acetaldehyde as a racemizing agent is released in situ from vinyl butanoate

  本研究介绍了脯氨酸和胡椒酸甲酯动态动力学拆分的方法。结果，开发了一种方法，该方法基于南极假丝酵母脂肪酶A将氨基酯的仲氨基与丁酸乙烯基酯酰化。在优化的方法中，乙醛作为外消旋剂从丁酸乙烯基酯中原位释放。三乙胺的存在，允许约。90％的外消旋脯氨酸和70％的胡椒酸甲酯以具有S-绝对构型的高度对映纯（ee = 97％）丁酰胺的形式被酰化。
• Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,
  作者：Dao Feng Xiang、Yury Patskovsky、Chengfu Xu、Alexander A. Fedorov、Elena V. Fedorov、Abby A. Sisco、J. Michael Sauder、Stephen K. Burley、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi100897u

  日期：2010.8.10

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).
• GUDASHEVA, T. A.;OSTROVSKAYA, R. U.;MAKSIMOVA, F. V.;CHUPPIN, A. V.;TROFI+, XIM.-FARMATS. ZH., 23,(1989) N, S. 276-281
  作者：GUDASHEVA, T. A.、OSTROVSKAYA, R. U.、MAKSIMOVA, F. V.、CHUPPIN, A. V.、TROFI+

  DOI：——

  日期：——
• PROCESSES FOR PRODUCING SOVAPREVIR
  申请人：Achillion Pharmaceuticals, Inc.

  公开号：EP2970195B1

  公开（公告）日：2017-08-02
• Synthesis of the Peptaibol Framework of the Anticancer Agent Culicinin D: Stereochemical Assignment of the AHMOD Moiety
  作者：Kuo-yuan Hung、Paul W. R. Harris、Margaret A. Brimble

  DOI：10.1021/ol302852q

  日期：2012.11.16

  The postulated structure of the potent anticancer peptaibol culicinin D has been synthesized using Fmoc-based solid-phase peptide synthesis (SPPS). Comparison of the 1H NMR data for the reported structure of culicinin D with the data obtained for the two synthetic polypeptides epimeric at C-6 in the AHMOD unit established the C-6 stereochemistry of the AHMOD residue in the natural product to be (R)

  使用基于Fmoc的固相肽合成（SPPS）合成了有效的抗癌肽肽culicinin D的假定结构。所报告的culicinin D结构的1 H NMR数据与在AHMOD单元中C-6处的两个合成多肽融合的合成数据的比较确定了天然产物AHMOD残基的C-6立体化学为（R）。