2-amino-2-deoxy-D-glucitol-6-phosphate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxy-D-glucitol-6-phosphate
• 英文别名: 2-Deoxy-2-Amino Glucitol-6-Phosphate；[(2R,3S,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexyl] dihydrogen phosphate
• 化学式: C₆H₁₆NO₈P
• 分子量: 261.169
• InChiKey: LBNVXZROMBUNNQ-SLPGGIOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  174
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 2-amino-2-deoxy-D-glucitol-6-phosphate 在 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以60%的产率得到N-n-butanoyl-2-amino-2-deoxy-D-glucitol-6-phosphate
  参考文献：
  名称：

  Hydrophobic derivatives of 2-amino-2-deoxy-d-glucitol-6-phosphate: A new type of d-Glucosamine-6-phosphate synthase inhibitors with antifungal action

  摘要：

  Several N-acyl and ester derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate (ADGP) have been synthesised and tested as inhibitors of fungal enzymes involved in early steps of chitin biosynthesis and for antifungal activity. All the tested derivatives were found to be much poorer inhibitors of the enzyme, D-glucosamine-6-phosphate (GIcN-6-P) synthase, than the parent compound but some of them exhibited much better antifungal activity. MIC values for the investigated compounds ranged between 10 mg mL(-1), found for ADGP and 0.3 mg mL(-1) for the most active derivative, namely ADGP dimethyl ester. Increased affinity of ADGP derivatives to the artificial immobilised cell membrane was correlated with their enhanced ability to be taken up by fungal cells by free diffusion. It was found that some of the examined derivatives behaved as 'pro-drugs' and after internalisation were converted into ADGP in the cell-free extract. This conversion was relatively rapid for ADGP esters but very slow for N-acyl derivatives. Results of our studies demonstrate a possibility of design and preparation of GIcN-6-P synthase inhibitors exhibiting antifungal activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00049-x

文献信息

• Glutamine fructose-y-phosphate amidotransferase (GFAT) inhibitors
  申请人：Bolin Robert David

  公开号：US20050113407A1

  公开（公告）日：2005-05-26

  Compounds of formula (I) are provided, wherein R 1 and R 2 are as designated in the specification. The compounds have utility for the treatment of type 2 diabetes mellitus.

  提供了式(I)的化合物，其中R1和R2如规范中所指定。这些化合物具有治疗2型糖尿病的用途。
• GLMS RIBOSWITCHES, STRUCTURE-BASED COMPOUND DESIGN WITH GLMS RIBOSWITCHES, AND METHODS AND COMPOSITIONS FOR USE OF AND WITH GLMS RIBOSWITCHES
  申请人：Breaker Ronald R.

  公开号：US20100324123A1

  公开（公告）日：2010-12-23

  The glmS riboswitch is a target for antibiotics and other small molecule therapies. Compounds can be used to stimulate, active, inhibit and/or inactivate the glmS riboswitch. The atomic structures of the glmS riboswitch can be used to design new compounds to stimulate, active, inhibit and/or inactivate riboswitches.

  glmS核酸开关是抗生素和其他小分子治疗的靶点。化合物可以用于刺激、激活、抑制和/或失活glmS核酸开关。glmS核酸开关的原子结构可用于设计新的化合物，以刺激、激活、抑制和/或失活核酸开关。
• Advanced drug development and manufacturing
  申请人：Los Alamos National Security, LLC

  公开号：EP2511844A2

  公开（公告）日：2012-10-17

  There is described an apparatus for measuring protein characteristics comprising an X-ray fluorescence (XRF) spectrometer comprising a source of polychromatic X-rays, an X-ray detector, a protein, a molecule that has been exposed to and at least weakly binds to the protein, a plurality of X-ray fluorescence signal data obtained by irradiating chemical elements in the protein and molecule with the polychromatic X-rays and a security system for maintaining records for the data from the plurality of X-ray fluorescence signal measurements. There is also described an x-ray microscope for measuring a sample.

  描述了一种测量蛋白质特性的仪器，该仪器包括一个 X 射线荧光 (XRF) 光谱仪，其中包括一个多色 X 射线源、一个 X 射线探测器、一个蛋白质、一个已暴露于该蛋白质并至少与该蛋白质弱结合的分子、通过用多色 X 射线照射蛋白质和分子中的化学元素而获得的多个 X 射线荧光信号数据，以及一个用于维护多个 X 射线荧光信号测量数据记录的安全系统。此外，还介绍了一种用于测量样品的 X 射线显微镜。
• Rational design of N-alkyl derivatives of 2-amino-2-deoxy-d-glucitol-6P as antifungal agents
  作者：Anna Melcer、Izabela Łącka、Iwona Gabriel、Marek Wojciechowski、Beata Liberek、Andrzej Wiśniewski、Sławomir Milewski

  DOI：10.1016/j.bmcl.2007.09.072

  日期：2007.12

  N-Alkyl and N,N-dialkyl derivatives of 2-amino-2-deoxy-D-glucitol-6P (ADGP) were synthesized and found to inhibit growth of human pathogenic fungi (MICs in the 0.08-0.625 mg mL(-1) range for the most active compounds). It was thus shown that N-alkylation of ADGP provides novel inhibitors of a fungal enzyme, glucosamine-6P synthase, exhibiting higher antifungal activity than the parent compound, due to the increased lipophilicity and better uptake by fungal cells. (c) 2007 Elsevier Ltd. All rights reserved.
• ISOQUINOLINE DERIVATIVES AND THEIR USE AS GFAT INHIBITORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1631551A2

  公开（公告）日：2006-03-08