6-(N4-Formyl-benzylpenicilloylamido)hexanoic Acid | 42454-69-3

• 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: 6-(N4-Formyl-benzylpenicilloylamido)hexanoic Acid
• 英文别名: ε-(N⁴-Formylbenzylpenicilloylamido)-capronsaeure；(4S)-2t-[(Ξ)-(5-carboxy-pentylcarbamoyl)-(2-phenyl-acetylamino)-methyl]-3-formyl-5,5-dimethyl-thiazolidine-4r-carboxylic acid
• CAS: 42454-69-3；129492-39-3
• 化学式: C₂₃H₃₁N₃O₇S
• 分子量: 493.581
• InChiKey: PLDRIMDWRDEAKH-IZOREMLJSA-N

物化性质

• 沸点：
  878.5±65.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  153.11
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (4S)-2t-[(Ξ)-(5-carboxy-pentylcarbamoyl)-(2-phenyl-acetylamino)-methyl]-5,5-dimethyl-thiazolidine-4r-carboxylic acid; mono-dibenzylamine salt 在 乙酸酐 作用下， 生成 6-(N4-Formyl-benzylpenicilloylamido)hexanoic Acid
  参考文献：
  名称：

  由青霉素基化合物形成D-青霉胺抗原决定簇的方面。

  摘要：

  AbstractThe formation of D‐penicillamine‐L‐cysteine mixed disulfide from benzylpenicilloic acid, benzylpenilloic acid and benzylpenicilloyl amide derivatives in L‐cysteine suspensions at pH 7,6 and 37° was studied. The reaction is faster than direct penicilloylation of proteins known to be a route to penicilloyl antigenic determinants. The production of S‐bound penicillamine on protein from penicilloyl compounds must therefore definitely be considered as a potential antigenforming step. The reaction may be partly if not fully blocked by acylation of the thiazolidine nitrogen of penicilloyl compounds. When formylation is applied a considerable reduction of the capacity of penicilloyl antigenic determinants to interact with anti‐penicilloyl antibody is noted. A D‐penicillamine‐specific test antigen was prepared by binding D‐penicillamine via thioether links to a partly succinylated poly‐L‐lysine. Clinical test reactions elicited with this conjugate and with penicilloic acid cannot be well correlated. Penicilloic acid probably detects reactions of undefined specificity in addition to D‐penicillamine‐specific ones.

  DOI：

  10.1002/hlca.19730560408