α-benzylserine | 51127-30-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: α-benzylserine
• 英文别名: 2-azaniumyl-2-benzyl-3-hydroxypropanoate
• CAS: 51127-30-1
• 化学式: C₁₀H₁₃NO₃
• mdl: MFCD01863305
• 分子量: 195.218
• InChiKey: ZMNNAJIBOJDHAF-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  417.1±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-benzylserine 在 sodium tetrahydroborate 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.58h， 生成 3-[(2-amino-2-benzyl-3-hydroxypropoxy)methyl]-N-[(1R)-1-(4-fluorophenyl)ethyl]-5-[methyl(methylsulfonyl)amino]benzamide
  参考文献：
  名称：

  [EN] BENZYLETHER AND BENZYLAMINO BETA-SECRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER'S DISEASE
  [FR] INHIBITEURS DE TYPE BENZYLETHER ET BENZYLAMINO DE BETA-SECRETASE POUR LE TRAITEMENT DE LA MALADIE D'ALZHEIMER

  摘要：

  公开号：

  WO2005032471A3
• 作为产物：
  描述：

  4-benzyl-2-phenyl-2-oxazoline-4-carboxylic acid methyl ester 在 盐酸 、 水 作用下， 反应 24.0h， 以98%的产率得到α-benzylserine
  参考文献：
  名称：

  Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate

  摘要：

  Described is the development of a new solid-phase synthetic method for alpha-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported substrate 12, the high chemical yield (up to 93%), and the mild cleavage conditions could make this method very practical for the synthesis of a-alkylserines. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.052

文献信息

• An Electrochemical Approach to Designer Peptide α-Amides Inspired by α-Amidating Monooxygenase Enzymes
  作者：Yutong Lin、Lara R. Malins

  DOI：10.1021/jacs.1c05718

  日期：2021.8.4

  amides are accessed in an efficient and epimerization-free approach by pairing an electrochemical oxidative decarboxylation with a tandem hydrolysis/reduction pathway. Resembling Nature’s dual enzymatic approach to bioactive primary α-amides, this method delivers secondary and tertiary amides bearing high-value functional motifs, including isotope labels and handles for bioconjugation. The protocol leverages

  通过将电化学氧化脱羧与串联水解/还原途径配对，以一种有效且无差向异构化的方法获得设计者 C 末端肽酰胺。类似于 Nature 对生物活性伯 α-酰胺的双重酶促方法，该方法提供具有高价值功能基序的仲和叔酰胺，包括同位素标记和用于生物偶联的手柄。该协议利用了 C 末端羧酸盐的固有反应性，与绝大多数蛋白质功能组兼容，并且在没有差向异构化的情况下进行，从而解决了与传统基于耦合的方法相关的主要限制。该方法的实用性通过合成天然产物 acidiphilamide A来举例说明关键的非对映选择性还原，以及生物活性肽和相关类似物，包括抗 HIV 先导肽和重磅炸弹癌症治疗剂亮丙瑞林。
• New cyclotetrapeptides with pro-angiogenic properties
  申请人：GENETADI Biotech, S.L.

  公开号：EP2407478A1

  公开（公告）日：2012-01-18

  New cyclotetrapeptides of formula (I) or their pharmaceutically acceptable salts, cyclo [Arg-Asp-(beta-Lactam)] (I) wherein (beta-Lactam) is a biradical of the formula (II) wherein the terminal NH group of the (beta-Lactam) is attached to the α-carbonyl group of the aspartic residue (Asp), and the terminal carbonyl group of the (beta-Lactam) is attached to the α-amino group the arginine residue (Arg); processes for their preparation, and pharmaceutical compositions containing them, as well as the said cyclotetrapeptides for use in human and animal therapy.

  新的环四肽化合物的化学式(I)或其药用盐，环[精-天冬氨酸-(β-内酰胺)](I)，其中(β-内酰胺)是化学式(II)的双自由基，其中(β-内酰胺)的末端NH基团连接到天冬氨酸残基(Asp)的α-羰基团，(β-内酰胺)的末端羰基团连接到精氨酸残基(Arg)的α-氨基团；它们的制备方法，含有它们的药物组合物，以及所述环四肽用于人类和动物治疗的用途。
• METHOD FOR PRODUCING SERINE DERIVATIVE AND PROTEIN USED FOR THE SAME
  申请人：Kuroda Shinji

  公开号：US20100317068A1

  公开（公告）日：2010-12-16

  The present invention describes a method for generating a serine derivative and an optically active isomer thereof by a convenient technique, and an enzyme and the like useful in the method. In the presence of the following protein (A) and/or (B) having an enzymatic activity, an α-amino acid is reacted with an aldehyde to form a serine derivative: (A) a protein comprising the amino acid sequence of SEQ ID NO:5, and (B) a protein comprising an amino acid sequence of SEQ ID NO: 5, but which includes substitution, deletion, insertion and addition of one or more amino acids and is able to catalyze the reaction to form the serine derivative.

  本发明描述了一种通过方便的技术生成丝氨酸衍生物及其光学活性异构体的方法，以及在该方法中有用的酶等。在具有以下酶活性的蛋白质（A）和/或（B）的存在下，α-氨基酸与醛反应形成丝氨酸衍生物：（A）包含SEQ ID NO:5氨基酸序列的蛋白质，和（B）包含SEQ ID NO:5氨基酸序列，但包括一个或多个氨基酸的置换、删除、插入和添加，并能催化反应形成丝氨酸衍生物。
• Discovery of Oxadiazoyl Tertiary Carbinamine Inhibitors of β-Secretase (BACE-1)
  作者：Hemaka A. Rajapakse、Philippe G. Nantermet、Harold G. Selnick、Sanjeev Munshi、Georgia B. McGaughey、Stacey R. Lindsley、Mary Beth Young、Ming-Tain Lai、Amy S. Espeseth、Xiao-Ping Shi、Dennis Colussi、Beth Pietrak、Ming-Chih Crouthamel、Katherine Tugusheva、Qian Huang、Min Xu、Adam J. Simon、Lawrence Kuo、Daria J. Hazuda、Samuel Graham、Joseph P. Vacca

  DOI：10.1021/jm061046r

  日期：2006.12.1

  We describe the discovery and optimization of tertiary carbinamine derived inhibitors of the enzyme beta-secretase (BACE-1). These novel non-transition-state-derived ligands incorporate a single primary amine to interact with the catalytic aspartates of the target enzyme. Optimization of this series provided inhibitors with intrinsic and functional potency comparable to evolved transition state isostere

  我们描述了酶β-分泌酶（BACE-1）的叔卡宾胺衍生抑制剂的发现和优化。这些新的非过渡态衍生的配体结合了一个伯胺与目标酶的催化天冬氨酸相互作用。该系列的优化为抑制剂提供了与进化的过渡态等位基因衍生的BACE-1抑制剂相当的内在和功能性抑制剂。
• Method for producing serine derivative and protein used for the same
  申请人：Kuroda Shinji

  公开号：US08372607B2

  公开（公告）日：2013-02-12

  The present invention describes a method for generating a serine derivative and an optically active isomer thereof by a convenient technique, and an enzyme and the like useful in the method. In the presence of the following protein (A) and/or (B) having an enzymatic activity, an α-amino acid is reacted with an aldehyde to form a serine derivative: (A) a protein comprising the amino acid sequence of SEQ ID NO:5, and (B) a protein comprising an amino acid sequence of SEQ ID NO: 5, but which includes substitution, deletion, insertion and addition of one or more amino acids and is able to catalyze the reaction to form the serine derivative.

  本发明描述了一种通过方便的技术生成丝氨酸衍生物及其光学活性异构体的方法，以及在该方法中有用的酶等。在具有以下酶活性的蛋白质(A)和/或(B)的存在下，α-氨基酸与醛反应形成丝氨酸衍生物：(A) 包含SEQ ID NO:5的氨基酸序列的蛋白质，以及(B) 包含SEQ ID NO:5的氨基酸序列，但包括一个或多个氨基酸的替换、缺失、插入和添加，并能够催化反应形成丝氨酸衍生物的蛋白质。