N,N'-di-D-galacturonoyl-putrescinamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: N,N'-di-D-galacturonoyl-putrescinamide
• 英文别名: (2S,3R,4S,5R,6S)-3,4,5,6-tetrahydroxy-N-[4-[[(2S,3R,4S,5R,6S)-3,4,5,6-tetrahydroxyoxane-2-carbonyl]amino]butyl]oxane-2-carboxamide
• 化学式: C₁₆H₂₈N₂O₁₂
• 分子量: 440.405
• InChiKey: YRMXFORXJDTGJD-DGQUGBMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  239
• 氢给体数：
  10
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  D-galacturonic acid 、 四亚甲基二胺 在 N-羟基丁二酰亚胺 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 反应 3.0h， 生成 N-D-galacturonoyl-putrescinamide 、 N,N'-di-D-galacturonoyl-putrescinamide
  参考文献：
  名称：

  Do polyamines contribute to plant cell wall assembly by forming amide bonds with pectins?

  摘要：

  Two new reducing glycoconjugates [N-D-galacturonoyl-putrescinamide (GalA-Put) and NN'-di-D-galacturonoyl-putrescinamide (GalA-Put-GalA)] and homogalacturonan-putrescine (GalA(n)-Put) conjugates were synthesised as model compounds representing possible amide (isopeptide) linkage points between a polyamine and either one or two pectic galacturonate residues. The amide bond(s) were stable to cold acid and alkali (2 M TFA and 0.1 M NaOH at 25 degrees C) but rapidly hydrolysed by these agents at 100 degrees C. The amide bond(s) were resistant to Driselase and to all proteinases tested, although Driselase digested GalA(n)-Put, releasing fragments such as GalA(3)-Put-GalA(3). To trace the possible formation of GalA-polyamine amide bonds in vivo, we fed Arabidopsis and rose cell-cultures and chickpea internodes with [C-14]Put. About 20% of the C-14 taken up was released as (14) CO2, indicating some catabolism. An additional similar to 73% of the C-14 taken up (in Arabidopsis), or similar to 21% (in rose), became ethanol-insoluble, superficially suggestive of polysaccharide-Put covalent bonding. However, much of the ethanol-inextractable C-14 was subsequently extractable by acidified phenol or by cold I M TFA. The small proportion of radioactive material that stayed insoluble in both phenol and TFA was hydrolysable by Driselase or hot 6 M HCl, yielding C-14-oligopeptides and/or amino acids (including Asp, Glu, Gly, Ala and Val); no free C-14-polyamines were released by hot HCl. We conclude that if pectin-polyamine amide bonds are present, they are a very minor component of the cell walls of cultured rose and Arabidopsis cells and chickpea internodes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2005.08.017

文献信息

• Do polyamines contribute to plant cell wall assembly by forming amide bonds with pectins?
  作者：Marcello Lenucci、Gabriella Piro、Janice G. Miller、Giuseppe Dalessandro、Stephen C. Fry

  DOI：10.1016/j.phytochem.2005.08.017

  日期：2005.11

  Two new reducing glycoconjugates [N-D-galacturonoyl-putrescinamide (GalA-Put) and NN'-di-D-galacturonoyl-putrescinamide (GalA-Put-GalA)] and homogalacturonan-putrescine (GalA(n)-Put) conjugates were synthesised as model compounds representing possible amide (isopeptide) linkage points between a polyamine and either one or two pectic galacturonate residues. The amide bond(s) were stable to cold acid and alkali (2 M TFA and 0.1 M NaOH at 25 degrees C) but rapidly hydrolysed by these agents at 100 degrees C. The amide bond(s) were resistant to Driselase and to all proteinases tested, although Driselase digested GalA(n)-Put, releasing fragments such as GalA(3)-Put-GalA(3). To trace the possible formation of GalA-polyamine amide bonds in vivo, we fed Arabidopsis and rose cell-cultures and chickpea internodes with [C-14]Put. About 20% of the C-14 taken up was released as (14) CO2, indicating some catabolism. An additional similar to 73% of the C-14 taken up (in Arabidopsis), or similar to 21% (in rose), became ethanol-insoluble, superficially suggestive of polysaccharide-Put covalent bonding. However, much of the ethanol-inextractable C-14 was subsequently extractable by acidified phenol or by cold I M TFA. The small proportion of radioactive material that stayed insoluble in both phenol and TFA was hydrolysable by Driselase or hot 6 M HCl, yielding C-14-oligopeptides and/or amino acids (including Asp, Glu, Gly, Ala and Val); no free C-14-polyamines were released by hot HCl. We conclude that if pectin-polyamine amide bonds are present, they are a very minor component of the cell walls of cultured rose and Arabidopsis cells and chickpea internodes. (c) 2005 Elsevier Ltd. All rights reserved.