methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate | 215719-42-9

• 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: methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate
• 英文别名: methyl (2S,3R,4R)-4-benzamido-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidine-2-carboxylate
• CAS: 215719-42-9
• 化学式: C₁₈H₂₅N₃O₅
• 分子量: 363.414
• InChiKey: PVMSPRAQYVAYTP-MCIONIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate 在 palladium on activated charcoal N-羟基-7-氮杂苯并三氮唑 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 149.0h， 生成 [(3S,7R,8R,8aS)-7-(benzoylamino)-3-(carboxymethyl)octahydro-1,4-dioxopyrrolo[1,2-a]pyrazin-8-yl]ammonium trifluoroacetate
  参考文献：
  名称：

  利用衍生自(2S,3R,4R)-二氨基脯氨酸的模板合成和溶液构象β-发夹模拟物

  摘要：

  A novel template was synthesized for stabilizing beta-hairpin conformations in cyclic peptide mimetics. The template is a diketopiperazine derived formally from L-aspartic acid and (2S,3R,4R)-diaminoproline, the latter being available by an efficient synthetic route from vitamin C, The template was incorporated by solid-phase peptide synthesis into a cyclic loop mimetic containing the sequence (-Ala-Asn-Pro-Asn-Ala-Ala-template-). This mimetic was shown by NMR to adopt a stable beta-hairpin conformation in (D-8)DMSO solution. The template may prove to be: generally useful for creating small-molecule mimetics: of hairpin loops on proteins of diverse function.

  DOI：

  10.1002/(sici)1522-2675(20000216)83:2<444::aid-hlca444>3.0.co;2-r
• 作为产物：
  描述：

  (1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 水 、 氢气 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate
  参考文献：
  名称：

  Stabilisation of β-hairpin conformations in a protein surface mimetic using a bicyclic template derived from (2S,3R,4R)-diaminoproline

  摘要：

  通过固相肽合成技术，将(S)-天冬氨酸和(2S,3R,4R)-二氨基脯氨酸（可从维生素 C 中获得）作为二酮哌嗪正式偶联得到的三官能团模板并入含有-Ala-Asn-Pro-Asn-Ala-Ala-序列的蛋白质环状模拟物中；核磁共振分析表明，该模板在二甲基亚砜中具有稳定的δ-发夹构象。

  DOI：

  10.1039/a804412k

文献信息

• Stabilisation of β-hairpin conformations in a protein surface mimetic using a bicyclic template derived from (2S,3R,4R)-diaminoproline
  作者：Marc E. Pfeifer、John A. Robinson

  DOI：10.1039/a804412k

  日期：——

  A trifunctional template, derived by formal coupling of (S)-aspartic acid and (2S,3R,4R)-diaminoproline (available from vitamin C) as a diketopiperazine, was incorporated by solid-phase peptide synthesis into a protein loop mimetic containing the sequence -Ala-Asn-Pro-Asn-Ala-Ala-; this was shown by NMR analysis to adopt a stable β-hairpin conformation in DMSO.

  通过固相肽合成技术，将(S)-天冬氨酸和(2S,3R,4R)-二氨基脯氨酸（可从维生素 C 中获得）作为二酮哌嗪正式偶联得到的三官能团模板并入含有-Ala-Asn-Pro-Asn-Ala-Ala-序列的蛋白质环状模拟物中；核磁共振分析表明，该模板在二甲基亚砜中具有稳定的δ-发夹构象。
• Synthesis and Solution Conformation ofβ-Hairpin Mimetics Utilizing a Template Derived from (2S,3R,4R)-Diaminoproline
  作者：Marc E. Pfeifer、Kerstin Moehle、Anthony Linden、John A. Robinson

  DOI：10.1002/(sici)1522-2675(20000216)83:2<444::aid-hlca444>3.0.co;2-r

  日期：2000.2.16

  A novel template was synthesized for stabilizing beta-hairpin conformations in cyclic peptide mimetics. The template is a diketopiperazine derived formally from L-aspartic acid and (2S,3R,4R)-diaminoproline, the latter being available by an efficient synthetic route from vitamin C, The template was incorporated by solid-phase peptide synthesis into a cyclic loop mimetic containing the sequence (-Ala-Asn-Pro-Asn-Ala-Ala-template-). This mimetic was shown by NMR to adopt a stable beta-hairpin conformation in (D-8)DMSO solution. The template may prove to be: generally useful for creating small-molecule mimetics: of hairpin loops on proteins of diverse function.