2-methyldeoxyguanidinoproclavaminic acid | 440366-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 2-methyldeoxyguanidinoproclavaminic acid
• 英文别名: (2S)-5-(diaminomethylideneamino)-2-(3-methyl-2-oxoazetidin-1-yl)pentanoic acid
• CAS: 440366-47-2
• 化学式: C₁₀H₁₈N₄O₃
• 分子量: 242.278
• InChiKey: UILWLIOLKBKWLP-MLWJPKLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  122
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyldeoxyguanidinoproclavaminic acid 在 盐酸 作用下， 反应 1.0h， 生成 2-methyl-N²-(2-carboxyethyl)-L-arginine
  参考文献：
  名称：

  Enzymatic Synthesis of Monocyclic β-Lactams

  摘要：

  An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N-2-(2-carboxyethyl)-L-arginine was synthesised and found to be a substrate for the enzyme. The epimeric products were characterised by H-1 NMR and mass spectrometric analyses. The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00806-x
• 作为产物：
  描述：

  (S)-5-Benzyloxycarbonylamino-2-(3-methyl-2-oxo-azetidin-1-yl)-pentanoic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-methyldeoxyguanidinoproclavaminic acid
  参考文献：
  名称：

  Enzymatic Synthesis of Monocyclic β-Lactams

  摘要：

  An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N-2-(2-carboxyethyl)-L-arginine was synthesised and found to be a substrate for the enzyme. The epimeric products were characterised by H-1 NMR and mass spectrometric analyses. The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00806-x

文献信息

• Enzymatic Synthesis of Monocyclic β-Lactams
  作者：Mark C Sleeman、Colin H MacKinnon、Kirsty S Hewitson∗、Christopher J Schofield

  DOI：10.1016/s0960-894x(01)00806-x

  日期：2002.2

  An Mg2+ and ATP dependent beta-lactam synthetase (BLS) catalyses formation of a beta-lactam ring during the biosynthesis of clavulanic acid, an important beta-lactamase inhibitor. An epimeric mixture of a 2-methylated derivative of the natural BLS substrate N-2-(2-carboxyethyl)-L-arginine was synthesised and found to be a substrate for the enzyme. The epimeric products were characterised by H-1 NMR and mass spectrometric analyses. The results suggest that a modified version of BLS might be used to catalyse the preparation of intermediates useful for the synthesis of beta-lactam antibiotics. (C) 2002 Elsevier Science Ltd. All rights reserved.