biotinylglycylglycine

• 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: biotinylglycylglycine
• 英文别名: biotin-GG；2-[[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]acetyl]amino]acetic acid
• 化学式: C₁₄H₂₂N₄O₅S
• 分子量: 358.418
• InChiKey: MHTHBMUCLUMYKP-RVBZMBCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  biotinylglycylglycine 在 对硝基苯酚 、 溶剂黄146 作用下， 反应 21.0h， 生成 (+/-)-N⁵-biotinylglycylglycyl-trans-5-amino-2-hydroxy-3-(4-phenylpiperidino)tetralin
  参考文献：
  名称：

  Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)

  摘要：

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.

  DOI：

  10.1021/jm00126a013
• 作为产物：
  描述：

  双甘肽 、 (+)-生物素 4-硝基苯酯 在 吡啶 、 氢氧化钾 作用下， 以 水 为溶剂， 反应 1.25h， 以83%的产率得到biotinylglycylglycine
  参考文献：
  名称：

  Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)

  摘要：

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.

  DOI：

  10.1021/jm00126a013

文献信息

• Profiling human Src homology 2 (SH2) domain proteins and ligand discovery using a peptide-hybrid small molecule microarray
  作者：Jiaqi Fu、Zhenkun Na、Mahesh Uttamchandani、Shao Q. Yao

  DOI：10.1039/c3cc45413d

  日期：——

  A 396-member peptide-hybrid small molecule microarray was fabricated to profile small molecule ligands across 15 SH2 proteins, revealing hits against Lck and Grb2.

  制备了一个包含396个肽-杂交小分子微阵列，以对15种SH2蛋白进行小分子配体的分析，发现了对Lck和Grb2的有效结合。
• Rapid Affinity‐Based Fingerprinting of 14‐3‐3 Isoforms Using a Combinatorial Peptide Microarray
  作者：Candy H. S. Lu、Hongyan Sun、Farhana B. Abu Bakar、Mahesh Uttamchandani、Wei Zhou、Yih‐Cherng Liou、Shao Q. Yao

  DOI：10.1002/anie.200801395

  日期：2008.9.15
• ROGERS, GARY A.;PARSONS, STANLEY M.;ANDERSON, D. C.;NILSSON, LENA M.;BAHR+, J. MED. CHEM., 32,(1989) N, C. 1217-1230
  作者：ROGERS, GARY A.、PARSONS, STANLEY M.、ANDERSON, D. C.、NILSSON, LENA M.、BAHR+

  DOI：——

  日期：——
• [EN] ENANTIOMERIC SCREENING PROCESS, AND COMPOSITIONS THEREFOR<br/>[FR] PROCEDE DE CRIBLAGE ENANTIOMERE ET COMPOSITIONS POUR CE PROCEDE
  申请人：——

  公开号：WO1997035194A2

  公开（公告）日：1997-09-25

  [EN] The present invention makes available a powerful directed approach for identifying enantioselective compounds which bind to biological targets. As a general overview, the present invention relates, in one aspect, to a method for identifying compounds which interact with a target molecule, by (i) contacting a screening molecule with a variegated compound library, wherein the screening molecule comprises solid target molecule, or the enantiomer thereof if the target molecule is chiral; (ii) selecting, from the library, compounds which have a desired interaction with the target molecule; and (iii) testing the ability of the enantiomer of a compound selected in step (ii) to interact with the target molecule.
• Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogs of trans-2-(4-phenylpiperidino)cyclohexanol (vesamicol)
  作者：Gary A. Rogers、Stanley M. Parsons、D. C. Anderson、Lena M. Nilsson、Ben A. Bahr、Wayne D. Kornreich、Rose Kaufman、Robert S. Jacobs、Bernard Kirtman

  DOI：10.1021/jm00126a013

  日期：1989.6

  Eighty-four analogues and derivatives of the acetylcholine-storage-blocking drug trans-2-(4-phenylpiperidino)-cyclohexanol (vesamicol) were synthesized, and their potencies were evaluated with the acetylcholine active-transport assay utilizing purified synaptic vesicles from Torpedo electric organ. The parent drug exhibits enantioselectivity, with (-)-vesamicol being 25-fold more potent than (+)-vesamicol. The atomic structure and absolute configuration of (+)-vesamicol were determined by X-ray crystallography. The absolute configuration of (-)-vesamicol is 1R,2R. Structure-activity evidence indicates that (-)-vesamicol does not act as an acetylcholine analogue. Alterations to all three rings can have large effects on potency. Unexpectedly, analogues locking the alcohol and ammonium groups trans-diequatorial or trans-diaxial both exhibit good potency. A potent benzovesamicol family has been discovered that is suitable for facile elaboration of the sort useful in affinity labeling and affinity chromatography applications. A good correlation was found between potencies as assessed by the acetylcholine transport assay and LD50 values in mouse.