(S)-tert-butyl 2-amino-3-(p-tolyl)propanoate | 923276-08-8

• 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)-tert-butyl 2-amino-3-(p-tolyl)propanoate
• 英文别名: (S)-(p-metyl phenyl) alanine tert-butyl ester；tert-butyl (2S)-2-amino-3-(4-methylphenyl)propanoate
• CAS: 923276-08-8
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: FNWRKKNMDIEZIT-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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)-tert-butyl 2-amino-3-(p-tolyl)propanoate 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-(p-Me-Phe)
  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-L-4-甲基苯丙氨酸 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)-tert-butyl 2-amino-3-(p-tolyl)propanoate
  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

• Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts
  作者：Jordi Rull、José Juan Jara、Rosa M. Sebastián、Adelina Vallribera、Carmen Nájera、Jean-Pierre Majoral、Anne-Marie Caminade

  DOI：10.1002/cctc.201600283

  日期：2016.6.21

  The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O‐9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles

  制备了四种新的磷树枝状相转移催化剂，该催化剂在通过奎宁环烷基N原子的季铵化反应获得的表面上包含12（+）-金鸡尼盐。甘氨酸Schiff碱与苄基溴的不对称烷基化被用作基准反应，并且在辛可宁单元的O-9羟基上含有烯丙基的树枝状催化剂最为活跃。催化剂的回收和再利用可以连续进行五次，而不会损失活性，对映选择性仅略有降低。如果使用其他亲电试剂，则取代的苄基溴化物要比其他活化的烷基溴化物得到更好的结果，从而得到相应的R氨基酸衍生物。将这些结果与先前报道的类似金鸡铵盐的结果进行比较，结果表明，对于这种类型的有机催化，树状大分子可能比其他聚合物有更好的支持。
• Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt β-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative
  作者：Takashi Ooi、Yukitaka Uematsu、Keiji Maruoka

  DOI：10.1002/1615-4169(200206)344:3/4<288::aid-adsc288>3.0.co;2-8

  日期：2002.6

  allylation of glycine tert-butyl ester benzophenone Schiff base (1). This revealed the practical conditions for the asymmetric synthesis of both natural and unnatural α-amino acids, whose usefulness was demonstrated by the formal enantioselective synthesis of antibiotic L-azatyrosine.

  N-螺环 C2-对称手性季铵盐 (S,S)-3 [(S,S)-β-Np-NAS-Br] 的固有效率已在具有代表性的有机-水液-液相中进行了评估-甘氨酸叔丁酯二苯甲酮席夫碱（1）的转移苄基化和烯丙基化。这揭示了天然和非天然 α-氨基酸不对称合成的实际条件，其有用性通过抗生素 L-氮杂酪氨酸的正式对映选择性合成得到证明。
• LIGAND-CYTOTOXICITY DRUG CONJUGATE, PREPARING METHOD THEREFOR, AND APPLICATION THEREOF
  申请人：Jiangsu Hengrui Medicine Co. Ltd.

  公开号：EP3251698A1

  公开（公告）日：2017-12-06

  Provide are a ligand-cytotoxicity drug conjugate with a general formula of PC-L-Dr, a preparing method thereof, and applications of the ligand-cytotoxicity drug conjugate and pharmaceutical compositions comprising the same in preparing drugs for treating cancers by means of receptor regulation.

  提供一种通式为 PC-L-Dr 的配体-毒性药物共轭物及其制备方法，以及该配体-毒性药物共轭物和包含该配体-毒性药物共轭物的药物组合物在制备通过受体调节治疗癌症的药物中的应用。
• [EN] LIGAND-CYTOTOXICITY DRUG CONJUGATE, PREPARING METHOD THEREFOR, AND APPLICATION THEREOF<br/>[FR] CONJUGÉ LIGAND-MÉDICAMENT CYTOTOXIQUE, PROCÉDÉ DE PRÉPARATION DUDIT CONJUGUÉ ET APPLICATION DUDIT CONJUGUÉ<br/>[ZH] 配体-细胞毒性药物偶联物、其制备方法及其应用
  申请人：JIANGSU HENGRUI MEDICINE CO

  公开号：WO2016127790A1

  公开（公告）日：2016-08-18

  提供了一种通式（I）为PC-L-Dr的配体-细胞毒性药物偶联物，其制备方法以及该配体-细胞毒性药物偶联物及含有其的药物组合物通过受体调节在制备治疗癌症的药物中的用途。
• EP3251698
  申请人：——

  公开号：——

  公开（公告）日：——