(4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid | 79236-62-7

• 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: (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid
• 英文别名: Pyochelin I；pyochelin；Pch；(2r,4r)-2-[(4r)-2-(2-Hydroxyphenyl)-4,5-Dihydro-1,3-Thiazol-4-Yl]-3-Methyl-1,3-Thiazolidine-4-Carboxylic Acid
• CAS: 79236-62-7
• 化学式: C₁₄H₁₆N₂O₃S₂
• 分子量: 324.425
• InChiKey: NYBZAGXTZXPYND-GBIKHYSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid 在 tetraethylammonium perchlorate 作用下， 以 甲醇 、 水 为溶剂， 生成 bis(pyochelin(2-))copper(II) 、 bis(pyochelin(1-))copper(II) 、 (pyochelin(2-))(pyochelin(1-))copper(II)(1-)
  参考文献：
  名称：

  Pyochelin，铜绿假单胞菌的铁载体：铁（iii），铜（ii）和锌（ii）配合物的理化特性†

  摘要：

  铜绿假单胞菌是一种机会病原体，它合成了两种主要的铁载体，吡啶酮（Pvd）和pyochelin（Pch），以满足其对铁的需求（III）。如果在文献中很好地描述了Pvd对铁（III）（pFe = 27.0）的高亲和力和特异性，那么Pch对生物相关金属（Fe（III），Cu（II）或Zn（II）的理化和配位特性））几乎没有被调查过。我们报告了对Pch的彻底物理化学研究（电位法，分光光度法，ESI / MS），强调了其对Fe 3+的中等但显着更高的亲和力（在p [H] 7.4时pFe = 16.0），比以前报道的要高。我们还证明，Pch强烈螯合二价金属，例如Zn（II）（p [H] 7.4时pZn = 11.8）和Cu（II）（p [H] 7.4时pCu = 14.9），并主要形成1：2（M 2+ / Pch）复合物。动力学研究表明，铁Pch配合物的形成过程是通过Eigen-Wilkins离解性配

  DOI：

  10.1039/c1dt11804h
• 作为产物：
  描述：

  dihydroaeruginoic acid 在 lithium aluminium tetrahydride 、 TEA 、 potassium acetate 、 氯磷酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4'R,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid
  参考文献：
  名称：

  Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues

  摘要：

  The synthesis and biological activities of four pyochelin analogues substituted in different parts of the molecule are reported: 5-NHBoc-pyochelin, 3"N-Boc-pyochelin, 3"-nor-NH-pyochelin and neopyochelin II, the enantiomer of natural pyochelin. All these compounds complex iron(III) and transport it at different rates into the cells of Pseudomonas aeruginosa. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00010-6

文献信息

• Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin
  作者：Akira Ino、Akira Murabayashi

  DOI：10.1016/s0040-4020(01)00012-6

  日期：2001.3

  Total synthesis of yersiniabactin, a siderophore from cultures of the bacterium Yersinia enterocolitica, was accomplished. Chirality at the readily racemizable C-9 carbon was preserved during cyclization of β-hydroxythioamide by means of Burgess reagent leading to thiazoline. Based on its synthesis, the absolute configuration of natural yersiniabactin has been determined as 9R, 10RS, 12R, 13S and 19S

  完成了耶尔西菌素的全合成，这是一种来自小肠结肠炎耶尔森氏菌培养物的铁载体。在β-羟基硫酰胺的环化过程中，通过伯硫试剂生成噻唑啉，可以保持易于消旋的C-9碳的手性。根据它的合成，天然耶尔森杆菌的绝对构型已被确定为9 - [R，10个RS，12 - [R，13小号和19小号。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。
• Stereochemical Assignment of the Pyochelins
  作者：Kenneth L. Rinehart、Andrew L. Staley、Scott R. Wilson、Robert G. Ankenbauer、Charles D. Cox

  DOI：10.1021/jo00114a029

  日期：1995.5

  The synthesis of pyochelin has been much improved but gives four stereoisomers. The stereochemistry of the two naturally occurring pyochelins I and II has been assigned, based on (1) the similarity of the NMR spectra of pyochelin I methyl ester to those for 4-methylpyochelin I methyl ester, whose X-ray structure has been determined and relative stereochemistry assigned; (2) comparison of the rotation of the natural material to that of pyochelin I methyl ester synthesized from N-methyl-L-cysteine methyl ester, which is not expected to epimerize during the synthesis and thus assigns pyochelin I methyl ester as 4'R,2 '' R,4 '' R; and (3) the known facile epimerization at C-2 '' of 2 ''-substituted thiazolidine-4-carboxylic acids, which assigns the other (unfavored) naturally occurring isomer, pyochelin II, as 4'R,2 '' S,4 '' R. The remaining two synthetic products, neopyochelin I methyl ester and neopyochelin II methyl ester, were assigned the stereochemistry 4'S,2 '' S,4 '' R and 4'S,2 '' R,4 '' R, respectively, based on (1) the use of N-methyl-L-cysteine methyl ester in their synthesis, which establishes C-4 '' as R; (2) the known instability at C-2 '', which favors neopyochelin II (2 '' R) over neopyochelin I (2 '' S); and (3) the requirement of nonidentity with pyochelins I and II, which requires the S configuration at C-4'.
• NOVEL PROTEINS SPECIFIC FOR PYOVERDINE AND PYOCHELIN
  申请人：SANOFI

  公开号：EP3259282A1

  公开（公告）日：2017-12-27
• PROCESSES AND HOST CELLS FOR GENOME, PATHWAY, AND BIOMOLECULAR ENGINEERING
  申请人：ENEVOLV, INC.

  公开号：US20160186168A1

  公开（公告）日：2016-06-30

  The present disclosure provides compositions and methods for genomic engineering.