Fmoc-Ala-(Me)Asn-OMe | 250264-96-1

• 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: Fmoc-Ala-(Me)Asn-OMe
• 英文别名: Fmoc-Ala-MeAsn-OMe；Fmoc-Ala-aMeAsn-OMe；methyl (2S)-4-amino-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]-2-methyl-4-oxobutanoate
• CAS: 250264-96-1
• 化学式: C₂₄H₂₇N₃O₆
• 分子量: 453.495
• InChiKey: PJZNDXPDTNNERQ-BSEYFRJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-Ala-(Me)Asn-OMe 在 吡啶 、 甲胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 (S)-2-Acetylamino-N-((S)-3-methyl-2,5-dioxo-pyrrolidin-3-yl)-propionamide
  参考文献：
  名称：

  Conformational Analysis of Peptides Containing Enantiomerically Pure α-Methylasparagine: Correspondence Between Computed and Solid State Structures

  摘要：

  Asparagine has a high frequency of occurrence in beta -turns. We have recently completed an asymmetric synthesis of alpha -methylasparagine suitably protected for incorporation into polypeptides, and report herein the synthesis and structure of dipeptide Ac-Ala-(Me)Asn-NHMe (1). The synthesis proceeds through the corresponding alpha -methylasparagine succinimide derivative. The three-dimensional structure of the dipeptide around the alpha,alpha -dialkylated alpha -amino acid is compared to that predicted for Ac-(Me)Asn-NHMe. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00880-2
• 作为产物：
  描述：

  Alloc-(cyclo-p-ClC6H4CH)-MeAsn-OMe 在 bis-triphenylphosphine-palladium(II) chloride 、 (C₃H₇)2NEt 、 3 A molecular sieve 、 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 Fmoc-Ala-(Me)Asn-OMe
  参考文献：
  名称：

  Enantiomerically Pure Tetrahydropyrimidinones in Asymmetric Synthesis:  Preparation of a Protected α-Methylasparagine Derivative and Corresponding Dipeptides

  摘要：

  Methyl ester 5a, available in enantiomerically pure form from the amino acid asparagine via a one-pot cyclization/protection sequence, followed by esterification, can be effectively deprotonated with LDA/DMPU/LiCl. Treatment with Mel affords the corresponding alkylated adduct in enantiomerically pure form, from which alpha-methylaspartic acid is obtained. Variation of the amine protection group allows for the isolation of a protected carboxylic acid/free amine derivative of alpha-methylasparagine. The utility of H-MeAsn-OMe is demonstrated in the formation of dipeptides.

  DOI：

  10.1021/jo9909296

文献信息

• Conformational Analysis of Peptides Containing Enantiomerically Pure α-Methylasparagine: Correspondence Between Computed and Solid State Structures
  作者：Stephanie A Hopkins、Joseph P Konopelski、Marilyn M Olmstead、Harold D Banks

  DOI：10.1016/s0040-4020(00)00880-2

  日期：2000.12

  Asparagine has a high frequency of occurrence in beta -turns. We have recently completed an asymmetric synthesis of alpha -methylasparagine suitably protected for incorporation into polypeptides, and report herein the synthesis and structure of dipeptide Ac-Ala-(Me)Asn-NHMe (1). The synthesis proceeds through the corresponding alpha -methylasparagine succinimide derivative. The three-dimensional structure of the dipeptide around the alpha,alpha -dialkylated alpha -amino acid is compared to that predicted for Ac-(Me)Asn-NHMe. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Enantiomerically Pure Tetrahydropyrimidinones in Asymmetric Synthesis:  Preparation of a Protected α-Methylasparagine Derivative and Corresponding Dipeptides
  作者：Stephanie A. Hopkins、Todd A. Ritsema、Joseph P. Konopelski

  DOI：10.1021/jo9909296

  日期：1999.10.1

  Methyl ester 5a, available in enantiomerically pure form from the amino acid asparagine via a one-pot cyclization/protection sequence, followed by esterification, can be effectively deprotonated with LDA/DMPU/LiCl. Treatment with Mel affords the corresponding alkylated adduct in enantiomerically pure form, from which alpha-methylaspartic acid is obtained. Variation of the amine protection group allows for the isolation of a protected carboxylic acid/free amine derivative of alpha-methylasparagine. The utility of H-MeAsn-OMe is demonstrated in the formation of dipeptides.