赭曲霉毒素 A-O-甲基,甲酯 | 4825-87-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 赭曲霉毒素及相关物质
• 中文名称: 赭曲霉毒素 A-O-甲基,甲酯
• 中文别名: 赭曲霉毒素A-O-甲基,甲酯
• 英文名称: ochratoxin A O-methyl ether methyl ester
• 英文别名: Ochratoxin A-O-methyl, methyl ester；methyl (2S)-2-[[(3R)-5-chloro-8-methoxy-3-methyl-1-oxo-3,4-dihydroisochromene-7-carbonyl]amino]-3-phenylpropanoate
• CAS: 4825-87-0
• 化学式: C₂₂H₂₂ClNO₆
• 分子量: 431.873
• InChiKey: RCTSSFFIVYPOQC-PXAZEXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  赭曲霉毒素 A-O-甲基,甲酯 在 sodium hydroxide 作用下， 反应 12.0h， 以95%的产率得到ochratoxin A O-methyl ether
  参考文献：
  名称：

  Synthesis and structural elucidation of analogs of ochratoxin A

  摘要：

  Five analogs of ochratoxin A (OA) including the ethylamide of OA (OE-OA), the D-phenylalanine form of OA (d-OA), the decarboxylated OA (DC-OA), the O-methyl ether of OA (OM-OA), and the methyl ester of ochratoxin alpha (M-O alpha) were synthesized using OA or ochratoxin alpha (O alpha) as the starting material. The reactions involved activation of OA to the N-hydroxysuccinimide ester (OA-NHS) and of O alpha to acyl chloride (O alpha-Cl) followed by nucleophilic substitution with primary amines, amino acids, and alcohols to form corresponding amides and esters. All analogs were obtained in pure forms, and all but OM-OA were crystallized. A simplified procedure for the isolation and crystallization of O alpha was also developed. The chemical structures of all analogs were elucidated using EI-MS and H-1 NMR. Other physicochemical parameters such as melting point, UV-vis absorption, fluorescence, and HPLC elution pattern for each analog are presented. The procedures that have been developed for the synthesis of the analogs of OA from OA or O alpha are simple and efficient. The reactions generally result in high yields of the desired compounds. The overall yields of final products range approximately from 85 to 90% of the starting materials. The analogs synthesized together with the natural analogs of OA can be used to establish the structure-activity relationship of OA and for metabolic and immunological studies.

  DOI：

  10.1021/jf00050a050
• 作为产物：
  描述：

  重氮甲烷 、 赭曲霉毒素A 以 甲醇 为溶剂， 反应 12.0h， 生成 赭曲霉毒素 A-O-甲基,甲酯
  参考文献：
  名称：

  Synthesis and structural elucidation of analogs of ochratoxin A

  摘要：

  Five analogs of ochratoxin A (OA) including the ethylamide of OA (OE-OA), the D-phenylalanine form of OA (d-OA), the decarboxylated OA (DC-OA), the O-methyl ether of OA (OM-OA), and the methyl ester of ochratoxin alpha (M-O alpha) were synthesized using OA or ochratoxin alpha (O alpha) as the starting material. The reactions involved activation of OA to the N-hydroxysuccinimide ester (OA-NHS) and of O alpha to acyl chloride (O alpha-Cl) followed by nucleophilic substitution with primary amines, amino acids, and alcohols to form corresponding amides and esters. All analogs were obtained in pure forms, and all but OM-OA were crystallized. A simplified procedure for the isolation and crystallization of O alpha was also developed. The chemical structures of all analogs were elucidated using EI-MS and H-1 NMR. Other physicochemical parameters such as melting point, UV-vis absorption, fluorescence, and HPLC elution pattern for each analog are presented. The procedures that have been developed for the synthesis of the analogs of OA from OA or O alpha are simple and efficient. The reactions generally result in high yields of the desired compounds. The overall yields of final products range approximately from 85 to 90% of the starting materials. The analogs synthesized together with the natural analogs of OA can be used to establish the structure-activity relationship of OA and for metabolic and immunological studies.

  DOI：

  10.1021/jf00050a050

文献信息

• Synthesis and structural elucidation of analogs of ochratoxin A
  作者：Hao Xiao、Ronald R. Marquardt、Andrew A. Frohlich、Yang Z. Ling

  DOI：10.1021/jf00050a050

  日期：1995.2

  Five analogs of ochratoxin A (OA) including the ethylamide of OA (OE-OA), the D-phenylalanine form of OA (d-OA), the decarboxylated OA (DC-OA), the O-methyl ether of OA (OM-OA), and the methyl ester of ochratoxin alpha (M-O alpha) were synthesized using OA or ochratoxin alpha (O alpha) as the starting material. The reactions involved activation of OA to the N-hydroxysuccinimide ester (OA-NHS) and of O alpha to acyl chloride (O alpha-Cl) followed by nucleophilic substitution with primary amines, amino acids, and alcohols to form corresponding amides and esters. All analogs were obtained in pure forms, and all but OM-OA were crystallized. A simplified procedure for the isolation and crystallization of O alpha was also developed. The chemical structures of all analogs were elucidated using EI-MS and H-1 NMR. Other physicochemical parameters such as melting point, UV-vis absorption, fluorescence, and HPLC elution pattern for each analog are presented. The procedures that have been developed for the synthesis of the analogs of OA from OA or O alpha are simple and efficient. The reactions generally result in high yields of the desired compounds. The overall yields of final products range approximately from 85 to 90% of the starting materials. The analogs synthesized together with the natural analogs of OA can be used to establish the structure-activity relationship of OA and for metabolic and immunological studies.