tautomycin diacid | 173322-74-2

• 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: tautomycin diacid
• 英文别名: tautomycin；TTMDA；(Z)-2-[(1R)-3-[(3R,4S,5R,8S,9S,12R)-12-[(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(3S)-3-methyl-4-oxopentyl]-1,7-dioxaspiro[5.5]undecan-2-yl]-5,9-dihydroxy-4-methoxy-2,8-dimethyl-7-oxotridecan-3-yl]oxy-1-hydroxy-3-oxopropyl]-3-methylbut-2-enedioic acid
• CAS: 173322-74-2
• 化学式: C₄₁H₆₈O₁₄
• 分子量: 784.983
• InChiKey: FLYBGKSOQRCWMB-SPVJCFRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  223
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  C₁₄H₁₆N₄O₂ 、 tautomycin diacid 在 sodium hydroxide 、 盐酸 作用下， 以 N,N-二甲基乙酰胺 、 水 、 乙腈 为溶剂， 反应 48.67h， 以80%的产率得到
  参考文献：
  名称：

  Development of a new protein labeling strategy, oxidation labeling. part 1: Preliminary evaluation and synthesis of tautomycin containing a metal coordinating unit

  摘要：

  In the current work we present Out preliminary evaluation of a new protein labeling strategy, namely oxidation labeling We found that a bis(2-picolyl) amine analogue coordinating Cu+ was able to oxidize histidine to oxo-histedine in a small peptide by generating reactive oxygen species upon exposure to hydrogen peroxide The bis(2-picolyl) amine unit was then incorporated into the natural product tautomycin via in oxime via an oxime linker. The compound, which showed good activity toward protein phosphatase 1 gamma (PP1 gamma), will be used in oxidation labeling studies with PP1 gamma (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2009.12.036
• 作为产物：
  描述：

  互变霉素 在 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 反应 5.0h， 以95%的产率得到tautomycin diacid
  参考文献：
  名称：

  Synthesis of photoaffinity probes of tautomycin

  摘要：

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.12.053

文献信息

• Synthesis of photoaffinity probes of tautomycin
  作者：Masakuni Kurono、Aya Shimomura、Minoru Isobe

  DOI：10.1016/j.tet.2003.12.053

  日期：2004.2

  Two types of photoaffinity: probe, which possesses a benzophenone or a diazirine photophore on the 2-position of tautomycin, were prepared in order to prove the details of binding site to PP1. These photoaffinity probes were designed on the basis of the structure-activity relationship; thus, the diacid moiety is indispensable. The selective introduction of photolabeling units on the 2-position of tautomycin was achieved through the 2-oxime of tautomycin diacid. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of the second generation photoaffinity probes of tautomycin
  作者：Magne O. Sydnes、Minoru Isobe

  DOI：10.1016/j.tet.2007.01.047

  日期：2007.3

  Five photoaffinity probes of tautomycin, which possess an aromatic azide with linker attached to the 2-position of tautomycin, were prepared in order to study the binding site of tautomycin with protein phosphatase 1 gamma. The photoaffinity probes were synthesized by selectively introducing the photolabeling units onto the 2-position of tautomycin by using oxime chemistry. (c) 2007 Elsevier Ltd. All rights reserved.
• Development of a new protein labeling strategy, oxidation labeling. part 1: Preliminary evaluation and synthesis of tautomycin containing a metal coordinating unit
  作者：Magne O. Sydnes、Atsushi Miyazaki、Minoru Isobe、Hiroshi Ohinata、Motoi Miyazu、Akira Takai

  DOI：10.1016/j.tet.2009.12.036

  日期：2010.2

  In the current work we present Out preliminary evaluation of a new protein labeling strategy, namely oxidation labeling We found that a bis(2-picolyl) amine analogue coordinating Cu+ was able to oxidize histidine to oxo-histedine in a small peptide by generating reactive oxygen species upon exposure to hydrogen peroxide The bis(2-picolyl) amine unit was then incorporated into the natural product tautomycin via in oxime via an oxime linker. The compound, which showed good activity toward protein phosphatase 1 gamma (PP1 gamma), will be used in oxidation labeling studies with PP1 gamma (C) 2010 Elsevier Ltd All rights reserved
• Protein phosphatase inhibitory activity of tautomycin photoaffinity probes evaluated at femto-molar level
  作者：Magne O. Sydnes、Masaki Kuse、Masakuni Kurono、Aya Shimomura、Hiroshi Ohinata、Akira Takai、Minoru Isobe

  DOI：10.1016/j.bmc.2007.11.034

  日期：2008.2

  Herein we describe the further improvement of our in-house developed firefly bioluminescence assay system for the determination of inhibition of protein phosphatase (PP). The advantage with the new system is higher sensitivity as well as being time and sample efficient. The inhibition activity of tautomycin with PP1 gamma was determined using the upgraded test system and K-i was found to be 4.5 nM, which compare favorably with the activity reported previously by others using different methods. The test system was then used in order to determine the activity of nine tautomycin (TTM) photoaffinity probes. One of the TTM photoaffinity probes (anti-10) was found to possess higher activity than the natural product itself with a K-i of 3.4 nM, while the remaining photoaffinity probes were found to possess K-i in the range of 8.0-213 nM. (C) 2007 Elsevier Ltd. All rights reserved.