Isopropenyl Succinimido Carbonate | 96935-01-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: Isopropenyl Succinimido Carbonate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) prop-1-en-2-yl carbonate
• CAS: 96935-01-2
• 化学式: C₈H₉NO₅
• 分子量: 199.163
• InChiKey: IELNLPVPJKOAAA-UHFFFAOYSA-N

物化性质

• 沸点：
  271.0±23.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  BOC-甘氨酸 、 Isopropenyl Succinimido Carbonate 在 N-甲基吗啉 作用下， 以 乙腈 为溶剂， 以76%的产率得到BOC-甘氨酸-N-羟基琥柏酰亚胺酯
  参考文献：
  名称：

  氯甲酸酯双异丙烯基（ipcf）在氨基酸上的合成-iii合成d'酯在表面上合成d'氨基酸

  摘要：

  氯甲酸异丙烯基酯（IPCF）用于制备混合的碳酸盐（芳基和异丙烯基），它们是氨基酸衍生物（特别是Boc衍生物）的活性酯合成的非常合适的试剂。

  DOI：

  10.1016/s0040-4039(00)98321-7
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 异丙烯基氯甲酸酯 在 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 4.0h， 以96%的产率得到Isopropenyl Succinimido Carbonate
  参考文献：
  名称：

  An Improved Method for the Synthesis of Active Esters ofN-Protected Amino Acids and Subsequent Synthesis of Dipeptides

  摘要：

  4-二甲氨基吡啶催化的混合碳酸酯3与N保护氨基酸4的反应生成了相应的活性酯5-9，接着通过与氨基酸10的氨解反应合成了二肽11-18。

  DOI：

  10.1055/s-1991-26545
• 作为试剂：
  描述：

  N-叔丁氧羰基-L-丙氨酸 、 3-(甲基氨基)丙酸叔丁酯 在 4-二甲氨基吡啶 、 Isopropenyl Succinimido Carbonate 作用下， 以 乙腈 、 1,4-二氧六环 为溶剂， 反应 25.0h， 以38%的产率得到N-Boc-L-Ala-N-Me-β-Ala-O-t-Bu
  参考文献：
  名称：

  Synthesis and activity of 5′-Uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A

  摘要：

  A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-alanyl- dipeptides were attached either via an ester linkage to the 5'-hydroxyl of uridine. or via an amide linkage to 5-amino-5-deoxyuridine. The most active inhibitor of Escherichia coli phosphoMurNAc-pentapeptide translocase (MraY) was 5'-O-((L)-Ala-N-methyl-beta-alanyl)-uridine (131), which also showed 97% enzyme inhibition at 2.35mM concentration, and showed antibacterial activity at 100 mug/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg2+. It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg2+. cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00270-0

文献信息

• Synthesis and activity of 5′-Uridinyl dipeptide analogues mimicking the amino terminal peptide chain of nucleoside antibiotic mureidomycin A
  作者：Nigel I Howard、Timothy D.H Bugg

  DOI：10.1016/s0968-0896(03)00270-0

  日期：2003.7

  A series of 5'-uridinyl dipeptides were synthesised which mimic the amino terminal chain of nucleoside antibiotic mureido omycin A. Aminoacyl-beta-alanyl- and aminoacyl-N-methyl-beta-alanyl- dipeptides were attached either via an ester linkage to the 5'-hydroxyl of uridine. or via an amide linkage to 5-amino-5-deoxyuridine. The most active inhibitor of Escherichia coli phosphoMurNAc-pentapeptide translocase (MraY) was 5'-O-((L)-Ala-N-methyl-beta-alanyl)-uridine (131), which also showed 97% enzyme inhibition at 2.35mM concentration, and showed antibacterial activity at 100 mug/mL concentration against Pseudomonas putida. Both the central N-methyl amide linkage and a 5' uridine ester linkage were required for highest biological activity. Enzyme inhibition was shown to be competitive with Mg2+. It is proposed that the primary amino terminus of the inhibitor binds in place of the Mg2+. cofactor at the MraY active site, positioned via a cis-N-methyl amide linkage. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Le chloroformiate d'isopropenyle (ipcf) en chimie des amino-acides et des peptides - iii synthese d'esters actifs d' amino acides n-proteges
  作者：M Jaouadi、C Selve、J.R Dormoy、B Castro、J Martinez

  DOI：10.1016/s0040-4039(00)98321-7

  日期：1985.1

  Isopropenyl chloroformate (IPCF) was used for preparation of mixed carbonates (Aryl and isopropenyl) which are very suitable reagents for active ester synthesis of amino acid derivatives ( Boc derivatives In particular).

  氯甲酸异丙烯基酯（IPCF）用于制备混合的碳酸盐（芳基和异丙烯基），它们是氨基酸衍生物（特别是Boc衍生物）的活性酯合成的非常合适的试剂。
• An Improved Method for the Synthesis of Active Esters of<i>N</i>-Protected Amino Acids and Subsequent Synthesis of Dipeptides
  作者：Kazuyoshi Takeda、Akira Ayabe、Masako Suzuki、Yaeko Konda、Yoshihiro Harigaya

  DOI：10.1055/s-1991-26545

  日期：——

  4-Dimethylaminopyridine-catalyzed reaction of mixed carbonates 3 with N-protected amino acids 4 gave the corresponding active esters 5-9, from which dipeptides 11-18 were synthesized by aminolysis with amino acids 10.

  4-二甲氨基吡啶催化的混合碳酸酯3与N保护氨基酸4的反应生成了相应的活性酯5-9，接着通过与氨基酸10的氨解反应合成了二肽11-18。