d-biotin | 224643-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: d-biotin
• 英文别名: 2-methylpropoxycarbonyl 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoate
• CAS: 224643-56-5
• 化学式: C₁₅H₂₄N₂O₅S
• 分子量: 344.432
• InChiKey: RVSWDLXJMQBXPS-GVXVVHGQSA-N

物化性质

• 密度：
  1.196±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  d-biotin 在 三正丁胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.08h， 生成
  参考文献：
  名称：

  Probing Adenosine Nucleotide-Binding Proteins with an Affinity-Labeled Nucleotide Probe and Mass Spectrometry

  摘要：

  质谱结合化学标记策略在生物分析中变得非常重要。本文中，我们描述了一种生物素化的酰基核苷酸探针在探测腺苷核苷酸结合蛋白中的应用。我们证明了该探针特异性地与两种纯化的腺苷核苷酸结合蛋白——大肠杆菌重组酶A（RecA）和酵母酒精脱氢酶I（YADH-I）的核苷酸结合位点的赖氨酸残基反应。通过LC-MS/MS，从核苷酸类似物与RecA或YADH-I反应产物的胰蛋白酶消化混合物中鉴定出一个带有特异性标记赖氨酸残基的单一偶联肽。该策略包括标记反应、酶消化、亲和纯化和LC-MS/MS分析，相对简单、快速且直接。该方法应普遍适用于鉴定其他蛋白质核苷酸结合位点的赖氨酸残基。生物素化的酰基核苷酸探针还允许从复杂蛋白混合物中富集和鉴定核苷酸结合蛋白；我们展示了从HeLa-S3和WM-266-4细胞的全细胞裂解物中可以鉴定出超过50种腺苷核苷酸结合蛋白。

  DOI：

  10.1021/ac0622375
• 作为产物：
  描述：

  D-生物素 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 d-biotin
  参考文献：
  名称：

  Design and synthesis of novel photoaffinity probes for study of the target proteins of oleanolic acid

  摘要：

  To explore the molecular mechanisms of oleanolic acid, two novel photoaffinity probes were synthesized based on the structure-activity relationship reported previously. Their potency were evaluated in an enzyme inhibition assay against rabbit muscle glycogen phosphorylase a (RMGPa), a known target protein of oleanolic acid. The inhibitory activity of probe 2 was only about two-fold less potent than the mother compound oleanolic acid. The photoaffinity labeling experiments were also performed and two proteins were specifically tagged by probe 2. The results suggest that the synthesized probes could be used as powerful tools to isolate and identify the target proteins of oleanolic acid. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.11.123

文献信息

• Affinity mass spectrometry from a tailored porous silicon surfaceElectronic supplementary information (ESI) available: synthesis and characterization of new compounds, experimental details. See http://www.rsc.org/suppdata/cc/b4/b408200a/
  作者：Jun-cai Meng、Gary Siuzdak、M. G. Finn

  DOI：10.1039/b408200a

  日期：——

  The development of chemically stable porous silicon (pSi) materials for DIOS (Desorption/Ionization on Silicon) mass spectrometry, covalent linkers cleaved in the DIOS laser pulse, and efficient methods for bond formation to immobilized species, allows for on-chip affinity purification and mass detection.

  开发化学稳定的多孔硅 (pSi) 材料用于 DIOS（在硅上解吸/电离）质谱、在 DIOS 激光脉冲中断裂的共价连接剂，以及有效的固定物种的键合形成方法，使得芯片上的亲和纯化和质量检测成为可能。
• Synthesis of novel biotin-based carborane amides
  作者：A. A. Telegina、D. A. Gruzdev、E. N. Chulakov、G. L. Levit、O. V. Koryakova、V. P. Krasnov

  DOI：10.1007/s11172-023-3970-3

  日期：2023.8

  A series of novel derivatives of d-biotin containing closo- and nido-carborane residues bound to the biotin carbonyl group either directly or via a linker were synthesized. The possibility of synthesizing a d-biotin conjugate containing two closo-carborane moieties and a glutamic acid residue was shown. The obtained compounds are of interest for biological testing as potential boron delivery agents

  合成了一系列新型d-生物素衍生物，其中含有直接或通过连接基与生物素羰基结合的近-和Nido-碳硼烷残基。显示了合成含有两个近碳硼烷部分和谷氨酸残基的d-生物素缀合物的可能性。所获得的化合物作为用于肿瘤的硼中子俘获疗法的潜在硼输送剂，对于生物测试具有重要意义。
• Protein and Small Molecule Recognition Properties of Deep Cavitands in a Supported Lipid Membrane Determined by Calcination-Enhanced SPR Spectroscopy
  作者：Ying Liu、Puhong Liao、Quan Cheng、Richard J. Hooley

  DOI：10.1021/ja102252d

  日期：2010.8.4

  This paper details the incorporation of a water-soluble deep cavitand into a membrane bilayer assembled onto a nanoglassified surface for study of molecular recognition in a membrane-mimicking setting. The cavitand retains its host properties, and real-time analysis of the host:guest properties of the membrane: cavitand complex via surface plasmon resonance and fluorescence microscopy is described. The host shows selectivity for choline-derived substrates, and no competitive incorporation of substrate is observed in the membrane bilayer. A variety of trimethylammonium-derived substrates are suitable guests, displaying varied binding affinities in a millimolar range. The membrane:cavitand:guest complexes can be subsequently used to capture NeutrAvidin protein at the membrane surface if a biotin-derived guest molecule is used. The surface coverage of NeutrAvidin is affected by the spacer used to derivatize the biotin. Increased distance from the bilayer allows a higher concentration of protein to be immobilized, suggesting a diminishing detrimental steric effect when the binding event is shifted away from the surface.
• Artificial Ligands of Streptavidin (ALiS): Discovery, Characterization, and Application for Reversible Control of Intracellular Protein Transport
  作者：Takuya Terai、Moe Kohno、Gaelle Boncompain、Shigeru Sugiyama、Nae Saito、Ryo Fujikake、Tasuku Ueno、Toru Komatsu、Kenjiro Hanaoka、Takayoshi Okabe、Yasuteru Urano、Franck Perez、Tetsuo Nagano

  DOI：10.1021/jacs.5b05672

  日期：2015.8.26

  Artificial ligands of streptavidin (ALiS) with association constants of similar to 10(6) M-1 were discovered by high-throughput screening of our chemical library, and their binding characteristics, including X-ray crystal structure of the streptavidin complex, were determined. Unlike biotin and its derivatives, ALiS exhibits fast dissociation kinetics and excellent cell permeability. The streptavidin-ALiS system provides a novel, practical compound-dependent methodology for repeated reversible cycling of protein localization between intracellular organella.
• Purification of DNA-Conjugate Products
  申请人：PHILOCHEM AG

  公开号：US20170073673A1

  公开（公告）日：2017-03-16

  This invention relates to the purification of nucleic acid conjugates, for example for use in DNA encoded chemical libraries. Reaction members that comprise nucleic acid conjugate reaction products and nucleic acid or nucleic acid conjugate reactants comprising a first reactive group are contacted with a capping molecule comprising a capture group. The capping molecule reacts with the first reactive group to form a covalent bond, thereby attaching the capture group to nucleic acid or nucleic acid conjugate reactants in reaction members. The nucleic acid or nucleic acid conjugate reactants are then removed from the reaction members using a binding member that binds the capture group, thereby producing a purified population of nucleic acid conjugate products. Methods of producing purified populations of nucleic acid conjugate products and nucleic acid chemical libraries are provided along with chemical libraries and kits.