Neopyochelin II | 164104-34-1

• 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: Neopyochelin II
• 英文别名: (4'S,2''R,4''R)-2'-(2-hydroxyphenyl)-3''-methyl-2'',3'',4'',4',5'-hexahydro-[2,4']-bisthiazolyl-4''-carboxylic acid；pyochelin II；(2R,4R)-2-[(4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazol-4-yl]-3-methyl-1,3-thiazolidine-4-carboxylic acid
• CAS: 164104-34-1
• 化学式: C₁₄H₁₆N₂O₃S₂
• 分子量: 324.425
• InChiKey: NYBZAGXTZXPYND-OUJBWJOFSA-N

物化性质

• 沸点：
  558.2±60.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

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

• 作为产物：
  描述：

  (4S)-2-[2-[tert-butyl(diphenyl)silyl]oxyphenyl]-4,5-dihydro-1,3-thiazole-4-carbaldehyde 在 四丁基氟化铵 、 potassium acetate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 生成 Neopyochelin II
  参考文献：
  名称：

  噻唑啉和含噻唑烷的天然产物的合成研究。第3部分：铁载体耶尔西菌素的总合成和绝对构型

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)00012-6

文献信息

• Bacterial siderophores: synthesis and biological activities of novel pyochelin analogues
  作者：A Zamri、I.J Schalk、F Pattus、M.A Abdallah

  DOI：10.1016/s0960-894x(03)00010-6

  日期：2003.3

  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.
• 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'.