N-Boc-D-proline-L-phenylalanine methyl ester | 74086-60-5

• 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: N-Boc-D-proline-L-phenylalanine methyl ester
• 英文别名: Boc-D-Pro-Phe-OMe；L-Phenylalanine, 1-[(1,1-dimethylethoxy)carbonyl]-D-prolyl-, methyl ester；tert-butyl (2R)-2-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 74086-60-5
• 化学式: C₂₀H₂₈N₂O₅
• 分子量: 376.453
• InChiKey: XYLTWJZHTZTSFD-JKSUJKDBSA-N

物化性质

• 沸点：
  538.8±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Boc-D-proline-L-phenylalanine methyl ester 在 2,6-二甲基吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (3S,8aR)-3-benzyl-2-prop-2-enoyl-6,7,8,8a-tetrahydro-3H-pyrrolo[1,2-a]pyrazine-1,4-dione
  参考文献：
  名称：

  2,5-二酮哌嗪，用于不对称Diels-Alder反应的新型手性助剂

  摘要：

  二酮哌嗪已经用作不对称Diels-Alder反应的手性助剂。发现环-S-苯丙氨酰基-R-脯氨酸（2）是这些助剂中最有前途的，并以高化学产率（78-95％）提供了Diels-Alder加合物，其内选择性通常大于9：1。观察到的非对映选择性可与先前最好的公开值进行比较。

  DOI：

  10.1016/s0040-4039(97)00769-7
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-D-proline 在 N-甲基吗啉 、 2,4-滴二甲胺盐 作用下， 以 氯仿 、 N,N-二甲基乙酰胺 为溶剂， 反应 0.75h， 生成 N-Boc-D-proline-L-phenylalanine methyl ester
  参考文献：
  名称：

  Solution structure of a synthetic N-glycosylated cyclic hexapeptide determined by NMR spectroscopy and MD calculations

  摘要：

  The synthesis and conformational analysis by NMR spectroscopy and MD calculations of the N-glycosylated cyclic hexapeptide cyclo(-D-Pro-Phe-Ala-[N-2-acetamido-2-desoxy-beta-D-glucopyranosyl)]Gln-Phe-Phe-) (I) and the cyclic hexapeptide precursor cyclo(-D-Pro-Phe-Ala-Glu(OtBu)-Phe-Phe-) (II) were carried out to study the influence of N-glycosylation on conformation of peptides. For both compounds, all of the distance constraints derived from 2D NOE measurements could not be satisfied by one conformation. Therefore, second conformers interconverting fast compared to the NMR time scale are assumed. The two conformations differ in the beta-turn structure between Ala3 and Phe6 (beta-II- or beta-I-turns, respectively). The beta-II'-turn about amino acids D-Pro1 and Phe2 is highly conserved in both MD simulations. The conformations were refined by using restrained MD simulations in vacuo and in water. Additional MD simulations with application of time-dependent distance constraints provide further information about the internal flexibility of I. The conformational equilibrium could be confirmed; several conformational changes were detected evidenced by a large number of torsion angle fluctuations during the time scale of the simulation. Both proposed backbone conformers were significantly populated. The averaging over coupling constants and NOE data reveal the high flexibility of the structure and the good agreement with experimental data for both I and II. The N-glycosylation does not affect the conformation or the overall shape of the peptide backbone or side chains. It has no influence on the hydrogen-binding pattern or on the fast dynamical equilibrium of the molecule.

  DOI：

  10.1021/ja00020a016

文献信息

• Asymmetric Organocatalysis Accelerated via Self‐Assembled Minimal Structures
  作者：Arianna Sinibaldi、Francesca Della Penna、Marco Ponzetti、Francesco Fini、Silvia Marchesan、Andrea Baschieri、Fabio Pesciaioli、Armando Carlone

  DOI：10.1002/ejoc.202101042

  日期：2021.10.21

  Self-assembling minimalistic peptides embedded with an organocatalytic moiety were designed and tested in a Michael reaction as a proof of concept for accelerated organocatalysis.

  嵌入有机催化部分的自组装简约肽在迈克尔反应中被设计和测试，作为加速有机催化的概念证明。
• Design and Synthesis of Oligopeptidic Parvulin Inhibitors
  作者：Nicola Relitti、A. Prasanth Saraswati、Gabriele Carullo、Alessandro Papa、Alessandra Monti、Rosaria Benedetti、Eugenia Passaro、Simone Brogi、Vincenzo Calderone、Stefania Butini、Sandra Gemma、Lucia Altucci、Giuseppe Campiani、Nunzianna Doti

  DOI：10.1002/cmdc.202200050

  日期：2022.6.3

  Pin1 and Pin4 with the selected compound explained the biochemical activity and pinpointed the chemical elements that may further improve the potency and selectivity of future peptide-based parvulin inhibitors.

  确定效力和选择性：直接结合实验允许鉴定甲基乙酰基-l-丙氨酰-l-组氨酰-l-脯氨酰-l-苯丙氨酸盐 ( 5k ) 作为一种有效的 Pin1 配体，其结合 Pin1 的亲和力高于 Pin4。Pin1 和 Pin4 的分子模型与所选化合物的比较分析解释了生化活性，并确定了可能进一步提高未来基于肽的 parvulin 抑制剂的效力和选择性的化学元素。
• Solution structure of a synthetic N-glycosylated cyclic hexapeptide determined by NMR spectroscopy and MD calculations
  作者：H. Kessler、H. Matter、G. Gemmecker、A. Kling、M. Kottenhahn

  DOI：10.1021/ja00020a016

  日期：1991.9

  The synthesis and conformational analysis by NMR spectroscopy and MD calculations of the N-glycosylated cyclic hexapeptide cyclo(-D-Pro-Phe-Ala-[N-2-acetamido-2-desoxy-beta-D-glucopyranosyl)]Gln-Phe-Phe-) (I) and the cyclic hexapeptide precursor cyclo(-D-Pro-Phe-Ala-Glu(OtBu)-Phe-Phe-) (II) were carried out to study the influence of N-glycosylation on conformation of peptides. For both compounds, all of the distance constraints derived from 2D NOE measurements could not be satisfied by one conformation. Therefore, second conformers interconverting fast compared to the NMR time scale are assumed. The two conformations differ in the beta-turn structure between Ala3 and Phe6 (beta-II- or beta-I-turns, respectively). The beta-II'-turn about amino acids D-Pro1 and Phe2 is highly conserved in both MD simulations. The conformations were refined by using restrained MD simulations in vacuo and in water. Additional MD simulations with application of time-dependent distance constraints provide further information about the internal flexibility of I. The conformational equilibrium could be confirmed; several conformational changes were detected evidenced by a large number of torsion angle fluctuations during the time scale of the simulation. Both proposed backbone conformers were significantly populated. The averaging over coupling constants and NOE data reveal the high flexibility of the structure and the good agreement with experimental data for both I and II. The N-glycosylation does not affect the conformation or the overall shape of the peptide backbone or side chains. It has no influence on the hydrogen-binding pattern or on the fast dynamical equilibrium of the molecule.
• 2,5-Diketopiperazines, new chiral auxiliaries for asymmetric Diels-Alder reactions
  作者：Thuy X.H. Le、Jacqueline C. Bussolari、William V. Murray

  DOI：10.1016/s0040-4039(97)00769-7

  日期：1997.6

  Diketopiperazines have been utilized as chiral auxiliaries for asymetric Diels-Alder reactions. Cyclo-S-phenylalanyl-R-proline (2) was found to be the most promising of these auxiliaries and afforded Diels-Alder adducts in high chemical yield (78–95%), with endo selectivities generally greater than 9:1. The diastereoselectivities observed were comparable to the best previously published values.

  二酮哌嗪已经用作不对称Diels-Alder反应的手性助剂。发现环-S-苯丙氨酰基-R-脯氨酸（2）是这些助剂中最有前途的，并以高化学产率（78-95％）提供了Diels-Alder加合物，其内选择性通常大于9：1。观察到的非对映选择性可与先前最好的公开值进行比较。