S-环己基丙氨酸叔丁酯 | 225780-73-4

• 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: S-环己基丙氨酸叔丁酯
• 英文名称: tert-butyl (S)-2-amino-3-cyclohexylpropanoate
• 英文别名: (S)-2-Amino-3-cyclohexyl-propionic acid tert-butyl ester；tert-butyl (2S)-2-amino-3-cyclohexylpropanoate
• CAS: 225780-73-4
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: BFHYVCSFGFKQIG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-环己基丙氨酸叔丁酯 在 TEA 、 1-羟基苯并三唑 、 苯甲醚 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 AcFTLDAD-(cyclohexyl)Ala
  参考文献：
  名称：

  Toward a Rational Design of Peptide Inhibitors of Ribonucleotide Reductase:  Structure−Function and Modeling Studies

  摘要：

  Mammalian ribonucleotide reductase, a chemotherapeutic target, has two subunits, mR1 and mR2, and is inhibited by AcF(1)TLDADF(7), denoted P7. P7 corresponds to the C-terminus of mR2 and competes with mR2 for binding to mR1. We report results of a structure-function analysis of P7, obtained using a new assay measuring peptide ligand binding to mR1, that demonstrate stringent specificity for Phe at F-7, high specificity for Phe at F-1, and little specificity for the N-acyl group. They support a structural model in which the dominant interactions of P7 occur at two mR1 sites, the F-1 and F-7 subsites. The model is constructed from the structure of Escherichia colt R1 (eR1) complexed with the C-terminal peptide from eR2, aligned sequences of mR1 and eR1, and the trNOE-derived structure of mR1-bound P7. Comparison of this model with similar models constructed for mR1 complexed with other inhibitory ligands indicates that increased F-1 subsite interaction can offset lower F-7 subsite interaction and suggests strategies for the design of new, higher affinity inhibitors.

  DOI：

  10.1021/jm000335r
• 作为产物：
  描述：

  FMOC-Β-环己基-L-丙氨酸 在 二乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 48.0h， 生成 S-环己基丙氨酸叔丁酯
  参考文献：
  名称：

  Toward a Rational Design of Peptide Inhibitors of Ribonucleotide Reductase:  Structure−Function and Modeling Studies

  摘要：

  Mammalian ribonucleotide reductase, a chemotherapeutic target, has two subunits, mR1 and mR2, and is inhibited by AcF(1)TLDADF(7), denoted P7. P7 corresponds to the C-terminus of mR2 and competes with mR2 for binding to mR1. We report results of a structure-function analysis of P7, obtained using a new assay measuring peptide ligand binding to mR1, that demonstrate stringent specificity for Phe at F-7, high specificity for Phe at F-1, and little specificity for the N-acyl group. They support a structural model in which the dominant interactions of P7 occur at two mR1 sites, the F-1 and F-7 subsites. The model is constructed from the structure of Escherichia colt R1 (eR1) complexed with the C-terminal peptide from eR2, aligned sequences of mR1 and eR1, and the trNOE-derived structure of mR1-bound P7. Comparison of this model with similar models constructed for mR1 complexed with other inhibitory ligands indicates that increased F-1 subsite interaction can offset lower F-7 subsite interaction and suggests strategies for the design of new, higher affinity inhibitors.

  DOI：

  10.1021/jm000335r

文献信息

• γ C–H Functionalization of Amines via Triple H-Atom Transfer of a Vinyl Sulfonyl Radical Chaperone
  作者：James H. Herbort、Taylor N. Bednar、Andrew D. Chen、T. V. RajanBabu、David A. Nagib

  DOI：10.1021/jacs.2c05266

  日期：2022.7.27

  to rapidly access homoallyl amines from their aliphatic precursors. The strategy employs a triple H-atom transfer (HAT) cascade, entailing (i) cobalt-catalyzed metal-HAT (MHAT), (ii) carbon-to-carbon 1,6-HAT, and (iii) Co–H regeneration via MHAT. A new class of sulfonyl radical chaperone (to rapidly access and direct remote, radical reactivity) enables remote desaturation of diverse amines, amino acids

  已经开发出一种选择性的远程去饱和方法，可以从脂肪族前体中快速获得高烯丙基胺。该策略采用三氢原子转移 (HAT) 级联，包括 (i) 钴催化金属 HAT (MHAT)、(ii) 碳到碳 1,6-HAT 和 (iii) Co-H 再生通过 MHAT。一类新型磺酰基分子伴侣（快速访问和直接远程自由基反应）能够实现多种胺、氨基酸和肽的远程去饱和，具有出色的位点、化学和区域选择性。该级联中关键的 C 到 C HAT 步骤经过计算设计，以满足热力学（键合强度）和动力学（极性）要求，并通过区域选择性、异构化和竞争实验对其进行了探讨。我们还中断了这种自由基转移脱氢，以实现 γ-选择性 C-Cl、C-CN 和 C-N 键的形成。