N-(3-formyl-2,2,5,5-tetramethylthiazolidinyl-4S-carbonyl)glycine tert-butyl ester | 266346-34-3

• 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: N-(3-formyl-2,2,5,5-tetramethylthiazolidinyl-4S-carbonyl)glycine tert-butyl ester
• 英文别名: N-(3-formyl-2,2,5,5-tetramethylthiazolidine-4S-carbonyl)-glycine t-butyl ester；tert-butyl 2-[[(4S)-3-formyl-2,2,5,5-tetramethyl-1,3-thiazolidine-4-carbonyl]amino]acetate
• CAS: 266346-34-3
• 化学式: C₁₅H₂₆N₂O₄S
• 分子量: 330.448
• InChiKey: WADDHIROGSOJAX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-formyl-2,2,5,5-tetramethylthiazolidinyl-4S-carbonyl)glycine tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以77%的产率得到[(2S)-1-(carboxymethylamino)-3-methyl-1-oxo-3-sulfanylbutan-2-yl]azanium;chloride
  参考文献：
  名称：

  N-Terminal Dipeptides of d(−)-Penicillamine as Sequestration Agents for Acetaldehyde

  摘要：

  Since acetaldehyde (AcH), a toxic oxidation product of ethanol, may play an etiologic role in the initiation of alcoholic liver disease, we had earlier pioneered the development of beta,beta-disubstituted-beta-mercapto-alpha-amino acids as AcH-sequestering agents. We now report the synthesis of a series of N-terminal dipeptides of D(-)-penicillamine, prepared from the synthon 3-formyl-2,2,5,5-tetramethylthiazolidine-4S-carboxylic acid (3), a cyclized N-protected derivative of D(-)-penicillamine. These dipeptides were equally or more effective than penicillamine in trapping AcH in a cell-free system. In experiments using a hepatocyte culture system, two of the dipeptides, D-penicillamylglycine (6a) and D-penicillamyl-beta-alanine (6d), at 1/20 the molar concentration of ethanol, lowered the concentration of ethanol-derived AcH by 79% and 84%, respectively, at 2 h. The presence of cyanamide tan inhibitor of aldehyde dehydrogenase) in the incubation medium resulted in a 45-fold increase in ethanol-derived AcH; nevertheless, dipeptides 8a and 6c (D-penicillamyl-alpha-aminoisobutyric acid) were able to reduce this AcH level by approximately one-third.

  DOI：

  10.1021/jm9902741
• 作为产物：
  描述：

  D-青霉胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(3-formyl-2,2,5,5-tetramethylthiazolidinyl-4S-carbonyl)glycine tert-butyl ester
  参考文献：
  名称：

  N-Terminal Dipeptides of d(−)-Penicillamine as Sequestration Agents for Acetaldehyde

  摘要：

  Since acetaldehyde (AcH), a toxic oxidation product of ethanol, may play an etiologic role in the initiation of alcoholic liver disease, we had earlier pioneered the development of beta,beta-disubstituted-beta-mercapto-alpha-amino acids as AcH-sequestering agents. We now report the synthesis of a series of N-terminal dipeptides of D(-)-penicillamine, prepared from the synthon 3-formyl-2,2,5,5-tetramethylthiazolidine-4S-carboxylic acid (3), a cyclized N-protected derivative of D(-)-penicillamine. These dipeptides were equally or more effective than penicillamine in trapping AcH in a cell-free system. In experiments using a hepatocyte culture system, two of the dipeptides, D-penicillamylglycine (6a) and D-penicillamyl-beta-alanine (6d), at 1/20 the molar concentration of ethanol, lowered the concentration of ethanol-derived AcH by 79% and 84%, respectively, at 2 h. The presence of cyanamide tan inhibitor of aldehyde dehydrogenase) in the incubation medium resulted in a 45-fold increase in ethanol-derived AcH; nevertheless, dipeptides 8a and 6c (D-penicillamyl-alpha-aminoisobutyric acid) were able to reduce this AcH level by approximately one-third.

  DOI：

  10.1021/jm9902741

文献信息

• N-terminal D(-)-penicillamine peptides as aldehyde sequestration agents
  申请人：——

  公开号：US20010041789A1

  公开（公告）日：2001-11-15

  The invention provides a compound of formula I: 1 wherein R 1 -R 3 have any of the values described in the specification; or a salt thereof. The compounds are useful as aldehyde sequestration agents (e.g., in the treatment of alcohol-related diseases). The invention also provides compositions comprising such compounds as well as therapeutic methods comprising their administration.

  该发明提供了一个公式I:1的化合物，其中R1-R3具有规范中描述的任何值；或其盐。这些化合物可用作醛缄合剂（例如，在治疗与酒精相关的疾病中）。该发明还提供了包含这些化合物的组合物，以及包括它们的给药的治疗方法。
• [EN] NOVEL FLUORESCENT DYES AND USES THEREOF<br/>[FR] NOUVEAUX COLORANTS FLUORESCENTS ET LEURS UTILISATIONS
  申请人：BECKMAN COULTER INC

  公开号：WO2011008912A1

  公开（公告）日：2011-01-20

  The present invention provides fluorescent dyes that are based on firefly luciferin structure. These dyes are optimally excited at shorter wavelengths and have Stokes shift of at least 50 nm. The fluorescent dyes of the invention are useful for preparation of dye-conjugates, which can be used in detection of an analyte in a sample.

  本发明提供基于萤火虫荧光素结构的荧光染料。这些染料在较短波长下被最佳激发，并具有至少50纳米的斯托克斯位移。本发明的荧光染料可用于制备染料偶联物，该偶联物可用于检测样品中的分析物。
• US6686336B2
  申请人：——

  公开号：US6686336B2

  公开（公告）日：2004-02-03
• [EN] N-TERMINAL D(-)-PENICILLAMINE PEPTIDES AS ALDEHYDE SEQUESTRATION AGENTS<br/>[FR] PEPTIDES D(-)-PENICILLAMINE N-TERMINAL UTILISES COMME AGENTS DE SEQUESTRATION D'ALDEHYDE
  申请人：NAGASAWA HERBERT T

  公开号：WO2001058928A1

  公开（公告）日：2001-08-16

  The invention provides a compound of formula (I): wherein R1-R3 have any of the values described in the specification; or a salt thereof. The compounds are useful as aldehyde sequestration agents (e.g., in the treatment of alcohol-related diseases). The invention also provides compositions comprising such compounds as well as therapeutic methods comprising their administration.
• N-Terminal Dipeptides of <scp>d</scp>(−)-Penicillamine as Sequestration Agents for Acetaldehyde
  作者：Jonathan F. Cohen、James A. Elberling、Eugene G. DeMaster、Renee C. Lin、Herbert T. Nagasawa

  DOI：10.1021/jm9902741

  日期：2000.3.1

  Since acetaldehyde (AcH), a toxic oxidation product of ethanol, may play an etiologic role in the initiation of alcoholic liver disease, we had earlier pioneered the development of beta,beta-disubstituted-beta-mercapto-alpha-amino acids as AcH-sequestering agents. We now report the synthesis of a series of N-terminal dipeptides of D(-)-penicillamine, prepared from the synthon 3-formyl-2,2,5,5-tetramethylthiazolidine-4S-carboxylic acid (3), a cyclized N-protected derivative of D(-)-penicillamine. These dipeptides were equally or more effective than penicillamine in trapping AcH in a cell-free system. In experiments using a hepatocyte culture system, two of the dipeptides, D-penicillamylglycine (6a) and D-penicillamyl-beta-alanine (6d), at 1/20 the molar concentration of ethanol, lowered the concentration of ethanol-derived AcH by 79% and 84%, respectively, at 2 h. The presence of cyanamide tan inhibitor of aldehyde dehydrogenase) in the incubation medium resulted in a 45-fold increase in ethanol-derived AcH; nevertheless, dipeptides 8a and 6c (D-penicillamyl-alpha-aminoisobutyric acid) were able to reduce this AcH level by approximately one-third.