β-Guanidino-L-α-tosylamino-propionsaeure | 3476-23-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: β-Guanidino-L-α-tosylamino-propionsaeure
• 英文别名: L-2-Tosylamino-3-guanidino-propionsaeure
• CAS: 3476-23-1
• 化学式: C₁₁H₁₆N₄O₄S
• 分子量: 300.338
• InChiKey: WMDHLOSKVDOAIT-VIFPVBQESA-N

物化性质

• 熔点：
  185-190 °C(Solv: acetic acid (64-19-7))
• 沸点：
  531.9±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.79
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  145.37
• 氢给体数：
  5.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  β-Guanidino-L-α-tosylamino-propionsaeure 在 氢溴酸 、 苯酚 作用下， 以 溶剂黄146 为溶剂， 生成 (2S)-2-amino-3-carbamimidamidopropanoic acid
  参考文献：
  名称：

  Rudinger,J. et al., Collection of Czechoslovak Chemical Communications, 1960, vol. 25, p. 2022 - 2028

  摘要：

  DOI：
• 作为产物：
  描述：

  N²-(toluene-4-sulfonyl)-L-asparagine 在 sodium hydroxide 、 溴 作用下， 生成 β-Guanidino-L-α-tosylamino-propionsaeure
  参考文献：
  名称：

  Effects of Arginine Homologues and other Guanidino Compounds on the ATP Level and Glucose Oxidation in Isolated Fat Cells

  摘要：

  The arginine homologues 2-amino-3-guanidinopropionic acid, 2-amino-4-guanidino-butyric acid and 2-amino-6-guanidinocaproic acid (= homoarginine) were synthesized and transformed into their methyl esters. The latter, together with arginine methyl esters. The latter, together with arginine methyl ester, arginine diethylamide and some guanidino compounds without the arginyl structure (agmatine, isopentyl-guanidine and n-butylbiguanide) were examined with regard to their behaviour on isolated fat cells, concerning the adrenalin-induced depression of the ATP level and the stimulation of glucose oxidation. The homoarginyl and arginyl derivatives counteracted the effect of adrenalin by re-elevating the ATP level, and thus they exerted an insulin-like activity. The esters were slightly active, whereas the arginine diethylamide and agmatine had a marked effect. The shorter homologues of arginine were totally inactive. However isopentyl-guanidine and butylbiguanide followed the effect of adrenalin: they additionally lowered the ATP level and therefore they acted in opposition to insulin. For comparative reasons the same compounds were tested with regard to their effects on glucose oxidation. The results were consistent with those quoted above: the homoarginyl and arginyl derivatives (agmatine included) forced the glucose oxidation similarly to insulin, the shorter homologues were inactive, isopentylguanidine and butylbiguanide decreased it.

  DOI：

  10.1515/bchm2.1975.356.s1.839