tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate | 77215-54-4

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 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: tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate
• 英文别名: (S)-tert-Butyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate；tert-butyl (2S)-3-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 77215-54-4
• 化学式: C₁₂H₂₄N₂O₄
• 分子量: 260.334
• InChiKey: OLMUCDWKBWSQKO-QMMMGPOBSA-N

物化性质

• 沸点：
  369.0±37.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，并保存在惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate 在 氨 、 碳酸氢钠 、 三乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 tert-butyl 2(S)--3-propanoate
  参考文献：
  名称：

  Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site

  摘要：

  Hippocampal CA1 pyramidal cell neurons are sensitized over 30-fold to depolarization by L-2-amino-4-phosphonobutanoic acid (L-AP4) following exposure to L-quisqualic acid. This phenomenon has been termed the QUIS effect. In the present study several novel L-quisqualic acid analogues have been synthesized and tested for their interaction with the different components of the QUIS-effect system. Replacement of the oxadiazolidinedione ring Of L-quisqualic acid with several other types of heterocyclic rings yielded the following quisqualic acid analogues: maleimide 2, N-methylmaleimide 3, N-(carboxymethyl)maleimide 4, succinimides 5A and 5B, and imidazolidinedione 6. None of these analogues were able to mimic the effects Of L-quisqualic acid and sensitize hippocampal CA1 neurons to depolarization by L-AP4. Also, unlike L-serine O-sulfate, L-homocysteinesulfinic acid, or L-alpha-aminoadipic acid, none of the analogues were able to preblock or reverse the QUIS effect. However, when the IC50 values for inhibition of the CA1 synaptic field potential of analogues 2-6 were determined both before and after hippocampal slices were exposed to L-quisqualic acid, the IC50 values of analogues 3 and 4 were found to decrease more than 7-fold. Thus, these two compounds behave like L-AP4 rather than L-quisqualic acid in this system in that they exhibit increased potencies in slices that have been pretreated with L-quisqualic acid even though they cannot themselves induce this sensitization. Compounds 3 and 4, therefore, represent the first non-phosphorus-containing compounds to which hippocampal neurons become sensitized following exposure to L-quisqualic acid. No change in the IC50 values was observed for 5A or 5B. Analogues 2 and 6, on the other hand, displayed a high potency for inhibition of the evoked field potential even prior to treatment of the slices with L-quisqualic acid.

  DOI：

  10.1021/jm00102a014
• 作为产物：
  描述：

  N-叔丁氧羰基丝氨酸叔丁酯 在 palladium on activated charcoal sodium azide 、 四丁基溴化铵 、 氢气 作用下， 以 吡啶 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 tert-butyl (2S)-3-amino-2-(tert-butoxycarbonylamino)propanoate
  参考文献：
  名称：

  Deamido Bleomycin A2 的全合成，抗肿瘤剂博来霉素的主要分解物

  摘要：

  抗肿瘤抗生素博来霉素的代谢失活被认为仅通过博来霉素水解酶的作用介导，博来霉素水解酶是一种在自然界中广泛分布的半胱氨酸蛋白酶。虽然博来霉素表现出的抗肿瘤活性谱被认为反映了博来霉素水解酶在宿主体内的解剖分布，但很少有人在化学或生化水平上表征推定失活的产物。本报告描述了 deamidobleomycin demethyl A(2) (3) 和 deamido bleomycin A(2) (4) 的合成，以及各自的苷元。这些化合物都可以通过关键中间体 N(alpha)-Boc-N(beta)-[1-amino-3(S)-(4-amino-6-carboxy-5-methylpyrimidin-2-yl)propion- 3-基]-(S)-β-氨基丙氨酸叔丁酯(16)。合成 deamido 博来霉素 A(2) 显示与博来霉素 A(2) 与人博来霉素水解酶处理形成的产品相同，如反相 HPLC 分析和

  DOI：

  10.1021/ja012741l

文献信息

• METHOD FOR PRODUCING ALKYLAMINE DERIVATIVE AND ITS PRODUCTION INTERMEDIATE OF ALKYLAMINE DERIVATIVE
  申请人：AJINOMOTO CO., INC.

  公开号：US20180079715A1

  公开（公告）日：2018-03-22

  A method for producing an alkylamine derivative having a urea bond represented by formula (I), or a salt thereof, comprises the following steps (a) and (b), step (a): and step (b): deprotecting as necessary the reaction product obtained in step (a). The production method suitable for industrialization of the alkylamine derivative having a urea bond represented by formula (I), which is a compound highly useful as an agent having CaSR agonist effects is provided.

  生产具有由化学式（I）表示的脲键的烷基胺衍生物或其盐的方法包括以下步骤（a）和（b），步骤（a）：和步骤（b）：必要时去保护步骤（a）中获得的反应产物。提供了适用于工业化的生产方法，用于具有CaSR激动剂效果的剂的烷基胺衍生物，其具有由化学式（I）表示的脲键，这是一种非常有用的化合物。
• Potential inhibitors of L-asparagine biosynthesis. 5. Electrophilic amide analogs of (S)-2,3-diaminopropionic acid
  作者：Michael Mokotoff、Lawrence W. Logue

  DOI：10.1021/jm00137a015

  日期：1981.5

  respectively. Deblocking of 6a-c gave the corresponding amino acids (S)-2-amino-3-(2-bromoacetamido)propionic acid hydrobromide (7a), (S)-2-amino-3-(2,2-dichloroacetamido)propionic acid (7b), and ethyl N-[(S)-2-amino-2-carboxyethyl]fumarate (7c). By a slightly different procedure, 5 was converted in two steps to (S)-2-amino-3-acetamidopropionic acid hydrobromide (7d). The inhibition of ASase by 7a-c at 1

  已经制备了三种（S）-2,3-二氨基丙酸（1，DAP）的亲电酰胺类似物作为L-天冬酰胺合成酶的潜在抑制剂（ASase，来自Novikoff肝癌，EC 6.3.5.4）。DAP被碳苯并（Cbz）基团选择性阻断，得到3-N-Cbz-DAP（2a）。用异丁烯将2a酯化，得到3-N-碳-苄氧基-（S）-2,3-二氨基丙酸叔丁酯（3a），然后在2位用叔丁氧羰基（Boc）封闭，得到叔丁基2-[（S）-（叔丁氧基羰基）氨基] -3-[（碳苯甲氧基）氨基]丙酸酯（4）。H2 / Pd对Cbz基团的选择性裂解产生了关键中间体2-N-（叔丁氧基羰基）-（S）-2,3-二氨基丙酸叔丁酯（5），该中间体通过N-羟基琥珀酰亚胺酯被酰化，含溴乙酸，二氯乙酸，和富马酸单乙酯得到2-[（（S）-（叔丁氧基羰基）-氨基] -3-（2-溴乙酰胺基）丙酸叔丁酯（6a），2-[（S）-（叔丁基）叔丁酯-丁氧基羰基）氨基] -3-（2
• The Nonribosomal Peptide Synthetase Enzyme DdaD Tethers <i>N</i>_β-Fumaramoyl-<scp>l</scp>-2,3-diaminopropionate for Fe(II)/α-Ketoglutarate-Dependent Epoxidation by DdaC during Dapdiamide Antibiotic Biosynthesis
  作者：Marie A. Hollenhorst、Stefanie B. Bumpus、Megan L. Matthews、J. Martin Bollinger、Neil L. Kelleher、Christopher T. Walsh

  DOI：10.1021/ja1072367

  日期：2010.11.10

  The gene cluster from Pantoea agglomerans responsible for biosynthesis of the dapdiamide antibiotics encodes an adenylation-thiolation didomain protein, DdaD, and an Fe(II)/α-ketoglutarate-dependent dioxygenase homologue, DdaC. Here we show that DdaD, a nonribosomal peptide synthetase module, activates and sequesters N(β)-fumaramoyl-l-2,3-diaminopropionate as a covalently tethered thioester for subsequent

  来自成团泛菌的基因簇负责 DAPdiamide 抗生素的生物合成，编码腺苷酸化-硫醇化双结构域蛋白 DdaD 和 Fe(II)/α-酮戊二酸依赖性双加氧酶同源物 DdaC。在这里，我们展示了 DdaD，一种非核糖体肽合成酶模块，激活和隔离 N(β)-延胡索酰基-1-2,3-二氨基丙酸酯作为共价连接的硫酯，用于随后对延胡索酰基进行氧化修饰。DdaC 催化共价结合的 N(β)-富马甲酰基-1-2,3-二氨基丙酰基-S-DdaD 物质的 Fe(II)-和 α-酮戊二酸依赖性环氧化，生成 N(β)-环氧琥珀酰胺-DAP (DAP = 2,3-二氨基丙酸酯）与 DdaD 的硫酯连接。水解释放后，
• [EN] THERAPEUTIC COMPOUNDS AND METHODS<br/>[FR] COMPOSÉS ET MÉTHODES THÉRAPEUTIQUES
  申请人：UNIV MINNESOTA

  公开号：WO2020010021A1

  公开（公告）日：2020-01-09

  Disclosed herein are compounds of formula I: (I) or pharmaceutically acceptable salts thereof, wherein R1, R2, and R3 may any of the values defined herein, as well as compositions comprising such compounds. Also disclosed are methods for treating diseases including neurodegenerative disorders such as Parkinson's Disease and Alzheimer's Disease.

  本文披露了以下式I的化合物：(I)或其药学上可接受的盐，其中R1、R2和R3可以是本文中定义的任何值，以及包含这种化合物的组合物。还披露了治疗疾病的方法，包括神经退行性疾病，如帕金森病和阿尔茨海默病。
• Inhibition of Glyoxalase I: The First Low-Nanomolar Tight-Binding Inhibitors
  作者：Swati S. More、Robert Vince

  DOI：10.1021/jm900382u

  日期：2009.8.13

  -based glyoxalase I inhibitors culminated in the discovery of the first single-digit nanomolar inhibitor. This study makes available key information about possible means to address the issues of metabolic instability, low potency, and synthetic complexicity that have plagued the area of glyoxalase I inhibition. Knowledge garnered from this study has implications in the design of inhibitors with higher

  对已知的基于S-（N-芳基-N-羟基氨基甲酰基）谷胱甘肽的乙二醛酶I抑制剂的结构进行了一系列合理的修改，最终发现了第一个个位数的纳摩尔抑制剂。这项研究提供了有关解决困扰乙二醛酶I抑制区域的代谢不稳定，药效低和合成复杂性问题的可能手段的关键信息。从这项研究中获得的知识对具有更高构象定义和更低肽特性的抑制剂的设计具有重要意义。