N-ethoxycarbonyl-maleamic acid | 106788-30-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-ethoxycarbonyl-maleamic acid
• 英文别名: N-Aethoxycarbonyl-maleamidsaeure；Maleinsaeure-mono-aethoxycarbonylamid；(Z)-4-(ethoxycarbonylamino)-4-oxobut-2-enoic acid
• CAS: 106788-30-1
• 化学式: C₇H₉NO₅
• 分子量: 187.152
• InChiKey: ZXDRZYCXCFNDHB-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,5-二氧代吡咯-1-甲酸乙酯 在 sodium carbonate 作用下， 生成 N-ethoxycarbonyl-maleamic acid
  参考文献：
  名称：

  肽的马来酰亚胺酸和马来酰基衍生物的制备及其某些性质。

  摘要：

  AbstractN‐Alkoxycarbonylmaleimides 3 have been prepared and used to convert amino acids to maleimido acids (6–8) in aqueous solution. The carboxyl group of maleimido acids can be activated for amide or peptide synthesis (e.g., in the N‐succinimidyl esters 10); t‐butyl‐based protecting groups can be cleaved without damage to the maleimide moiety. Peptides carrying maleimide groups are accessible either from the maleimido acids (e.g., 11b, 15) or by direct maleoylation (e.g., 16b). The maleoyl group can be cleaved off by successive mild alkaline and acid hydrolysis or by hydrazinolysis. The reactivity of maleimides toward thiol groups suggests the use of maleimido acids and maleoylpeptides for preparing a wide range of conjugates of biochemical interest.

  DOI：

  10.1002/hlca.19750580224

文献信息

• Yakushijin, Kenichi; Suzuki, Rika; Kawaguchi, Naoko, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 5, p. 2049 - 2055
  作者：Yakushijin, Kenichi、Suzuki, Rika、Kawaguchi, Naoko、Tsuboi, Yoshinori、Furukawa, Hiroshi

  DOI：——

  日期：——
• Matkovics et al., 1958, vol. 4, p. 134,141
  作者：Matkovics et al.

  DOI：——

  日期：——
• YAKUSHIJIN KENICHI; SUZUKI RIKA; KAWAGUCHI NAOKO; TSUBOI YOSHINORI; FURUK+, CHEM. AND PHARM. BULL., 34,(1986) N 5, 2049-2055
  作者：YAKUSHIJIN KENICHI、 SUZUKI RIKA、 KAWAGUCHI NAOKO、 TSUBOI YOSHINORI、 FURUK+

  DOI：——

  日期：——
• Preparation and Some Properties of Maleimido Acids and maleoyl derivatives of peptides
  作者：Oskar Keller、Josef Rudinger

  DOI：10.1002/hlca.19750580224

  日期：——

  AbstractN‐Alkoxycarbonylmaleimides 3 have been prepared and used to convert amino acids to maleimido acids (6–8) in aqueous solution. The carboxyl group of maleimido acids can be activated for amide or peptide synthesis (e.g., in the N‐succinimidyl esters 10); t‐butyl‐based protecting groups can be cleaved without damage to the maleimide moiety. Peptides carrying maleimide groups are accessible either from the maleimido acids (e.g., 11b, 15) or by direct maleoylation (e.g., 16b). The maleoyl group can be cleaved off by successive mild alkaline and acid hydrolysis or by hydrazinolysis. The reactivity of maleimides toward thiol groups suggests the use of maleimido acids and maleoylpeptides for preparing a wide range of conjugates of biochemical interest.