D-丝氨酸甲酯 | 24184-43-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丝氨酸类衍生物
• 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
• 中文名称: D-丝氨酸甲酯
• 英文名称: D-serine methyl ester
• 英文别名: methyl D-serinate；(R)-methyl 2-amino-3-hydroxypropanoate；methyl (R)-2-amino-3-hydroxypropanoate；methyl (2R)-2-amino-3-hydroxypropanoate
• CAS: 24184-43-8
• 化学式: C₄H₉NO₃
• 分子量: 119.12
• InChiKey: ANSUDRATXSJBLY-GSVOUGTGSA-N

物化性质

• 沸点：
  234.7±20.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  D-丝氨酸甲酯 在 Streptomyces spp. 82F₂ D-aminopeptidase 作用下， 以 二甲基亚砜 为溶剂， 反应 0.08h， 生成 D-丝氨酸
  参考文献：
  名称：

  Aminolytic reaction catalyzed by d-stereospecific amidohydrolases from Streptomyces spp

  摘要：

  From investigation of 2000 soil isolates, we identified two serine-type amidohydrolases that can hydrolyze D-aminoacyl derivatives from the culture supernatant of Streptomyces species 82F2 and 83D12. The enzymes, redesignated as 82F2-DAP and 83D12-DAP, were purified for homogeneity and characterized. Each enzyme had molecular mass of approximately 40 kDa, and each showed moderate stability with respect to temperature and pH. Among hydrolytic activities toward D-aminoacyl-pNAs, the enzymes showed strict specificity toward D-Phe-pNA, but showed broad specificity toward D-aminoacyl esters. The specific activity for D-Phe-pNA hydrolysis of 82F2-DAP was ten-fold higher than that of 83D12-DAP. As a second function, each enzyme showed peptide bond formation activity by its function of aminolysis reaction. Based on results of D-Phe D-Phe synthesis under various conditions, we propose a reaction mechanism for D-Phe D-Phe production. Furthermore, the enzymes exhibited peptide elongation activity, producing oligo homopeptide in a one-pot reaction. We cloned the genes encoding each enzyme, which revealed that the primary structure of each enzyme showed 30-60% identity with those of peptidases belonging to the clan SE, S12 peptidase family categorized as serine peptidase with D-stereospecificity. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.biochi.2011.04.020
• 作为产物：
  描述：

  N-Z-D-丝氨酸甲酯 在 10% palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 生成 D-丝氨酸甲酯
  参考文献：
  名称：

  Discovery of DA-1229: A potent, long acting dipeptidyl peptidase-4 inhibitor for the treatment of type 2 diabetes

  摘要：

  A series of beta-amino amide containing substituted piperazine-2-one derivatives was synthesized and evaluated as inhibitors of dipeptidyl pepdidase-4 (DPP-4) for the treatment of type 2 diabetes. As results of intensive SAR study of the series, (R)-4-[(R)-3-amino-4-(2,4,5-trifluorophenyl)-butanoyl]-3-(t-butoxymethyl)-piperazin-2-one (DA-1229) displayed potent DPP-4 inhibition pattern in several animal models, was selected for clinical development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.029

文献信息

• [EN] DIPEPTIDE AND TRIPEPTIDE EPOXY KETONE PROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE DIPEPTIDE ET DE TRIPEPTIDE ÉPOXY CÉTONE PROTÉASES
  申请人：ONYX THERAPEUTICS INC

  公开号：WO2014152127A1

  公开（公告）日：2014-09-25

  Provided herein are dipeptide and tripeptide epoxy ketone protease inhibitors, methods of their preparation, related pharmaceutical compositions, and methods of using the same. For example, provided herein are compounds of Formula (X): and pharmaceutically acceptable salts and compositions including the same. The compounds and compositions provided herein may be used, for example, in the treatment of proliferative diseases including cancer and autoimmune diseases.

  本文提供了二肽和三肽环氧酮蛋白酶抑制剂，其制备方法，相关的药物组合物，以及使用它们的方法。例如，本文提供了化合物的化学式（X）：及其药用盐和包括这些化合物的组合物。本文提供的化合物和组合物可以用于治疗增生性疾病，包括癌症和自身免疫疾病。
• Radical‐Mediated Acyl Thiol‐Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives
  作者：Joshua T. McLean、Pierre Milbeo、Dylan M. Lynch、Lauren McSweeney、Eoin M. Scanlan

  DOI：10.1002/ejoc.202100615

  日期：2021.8.6

  Radical-mediated acyl thiol-ene reactions between biologically relevant alkene and thioacid components enables rapid, chemoselective and high yielding thioester formation. This reaction in combination with substrates that enable intramolecular acyl transfer permits access to native and modified products beyond the thioether linkage.

  生物相关烯烃和硫代酸组分之间自由基介导的酰基硫醇-烯反应能够快速、化学选择性和高产率地形成硫酯。该反应与能够进行分子内酰基转移的底物结合，允许获得超出硫醚键的天然和修饰产物。
• Discovery of [1,2,4]Triazolo[4,3-<i>a</i>]pyridines as Potent Inhibitors Targeting the Programmed Cell Death-1/Programmed Cell Death-Ligand 1 Interaction
  作者：Mingze Qin、Qi Cao、Shuaishuai Zheng、Ye Tian、Haotian Zhang、Jun Xie、Hongbo Xie、Yajing Liu、Yanfang Zhao、Ping Gong

  DOI：10.1021/acs.jmedchem.9b00312

  日期：2019.5.9

  Inhibition of the programmed cell death-1 (PD-1)/programmed cell death-ligand 1 (PD-L1) interaction using small-molecule inhibitors is an emerging immunotherapeutic approach. A novel series of [1,2,4]triazolo[4,3- a]pyridines were designed and found to be potent inhibitors of the PD-1/PD-L1 interaction. Among them, compound A22 exhibited the most potent activity, as assessed by homogenous time-resolved

  使用小分子抑制剂抑制程序性细胞死亡1（PD-1）/程序性细胞死亡配体1（PD-L1）相互作用是一种新兴的免疫治疗方法。设计了一系列新的[1,2,4]三唑并[4,3-a]吡啶，并发现它们是PD-1 / PD-L1相互作用的有效抑制剂。其中，通过均相时间分辨荧光分析评估，化合物A22表现出最强的活性，IC50为92.3 nM。此外，在Hep3B / OS-8 / hPD-L1和CD3 T细胞的共培养模型中，A22剂量依赖性升高的干扰素-γ产生。我们得出的结论是，A22是开发PD-1 / PD-L1相互作用抑制剂的有前途的先导化合物。此外，我们探索了新合成的[1,2,4] triazolo [4，并证明了环融合策略可用于设计Bristol-Myers Squibb化学系列的类似物。这些研究为将来的药物设计铺平了道路。
• PYRIDOPYRIMIDONE DERIVATIVES, PREPARATION THEREOF, THERAPEUTIC USE THEREOF
  申请人：PERREAUT Pierre

  公开号：US20090048277A1

  公开（公告）日：2009-02-19

  The disclosure relates to pyrido[2,3-d]pyrimidone compounds, to the preparation thereof and to the therapeutic use thereof, wherein said compounds are of general formula (I): in the form of a base or of an addition salt with an acid which is pharmaceutically acceptable, in the form of hydrates or of solvates, and also in the form of enantiomers, diastereoisomers and a mixture thereof. The disclosure also relates to processes for preparing said compounds, to pharmaceutical compositions containing a compound of general formula (I), and to the therapeutic use of said compounds and compositions.

  本公开涉及吡啶[2,3-d]嘧啶酮化合物，其制备方法以及治疗用途，其中所述化合物为通用公式 (I)： 以碱的形式或与药物可接受的酸的加成盐的形式，以水合物的形式或溶剂化物的形式，以及以对映异构体、对映异构体和其混合物的形式。本公开还涉及制备所述化合物的方法，包含通用公式 (I) 化合物的药物组合物，以及所述化合物和组合物的治疗用途。
• [EN] AMIDINE SUBSTITUTED BETA - LACTAM COMPOUNDS, THEIR PREPARATION AND USE AS ANTIBACTERIAL AGENTS<br/>[FR] COMPOSÉS DE BÊTA-LACTAME À SUBSTITUTION AMIDINE, LEUR PRÉPARATION ET LEUR UTILISATION EN TANT QU'AGENTS ANTIBACTÉRIENS
  申请人：AICURIS GMBH & CO KG

  公开号：WO2013110643A1

  公开（公告）日：2013-08-01

  The present invention relates to novel β-lactam compounds of formula (I), their preparation and use. In particular, this invention relates to novel β-lactam compounds which are amidine substituted monobactam derivatives useful as antimicrobial agents and their preparation.

  本发明涉及式(I)的新型β-内酰胺化合物，它们的制备和使用。特别是，本发明涉及作为抗菌剂有用的新型β-内酰胺化合物，即取代脒的单巴坦衍生物及其制备方法。