4Hyp-Gly | 119324-36-6

• 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: 4Hyp-Gly
• 英文别名: N-(cis-4-hydroxy-L-prolyl)-glycine；N-(cis-4-Hydroxy-L-prolyl)-glycin；2-[[(2S,4S)-4-hydroxypyrrolidine-2-carbonyl]amino]acetic acid
• CAS: 119324-36-6
• 化学式: C₇H₁₂N₂O₄
• 分子量: 188.183
• InChiKey: WFDSWNXTPKLLOT-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S,4S)-1-(苄基羰基)-4-羟基吡咯烷-2-羧酸 在 三乙胺 、 氯甲酸异丁酯 作用下， 生成 4Hyp-Gly
  参考文献：
  名称：

  Davis; Adams, Archives of Biochemistry, 1955, vol. 57, p. 301,303

  摘要：

  DOI：

文献信息

• Absorption of Hydroxyproline-Containing Peptides in Vascularly Perfused Rat Small Intestine<i>in Situ</i>
  作者：Chinfang LIU、Kazuko SUGITA、Ken-ichi NIHEI、Koichi YONEYAMA、Hideyuki TANAKA

  DOI：10.1271/bbb.90050

  日期：2009.8.23

  To assess the digestion and assimilation of gelatin and gelatin hydrolysates, the in situ absorption of typical hydroxyproline-containing dipeptides, Pro-Hyp, Hyp-Gly, Ser-Hyp Ala-Hyp, and pentadecapeptide, (Pro-Hyp-Gly)5, was investigated in the rat small intestine. During vascular perfusion after the injection of Hyp-Gly, Pro-Hyp and (Pro-Hyp-Gly)5 into the jejunum, peptide-form Hyp but not free-Hyp gradually increased in the perfusate. In contrast, in the case of Ser-Hyp and Ala-Hyp, both free- and peptide-form Hyp rapidly increased. The presence of these dipeptides and the pentadecapeptide in the perfusates was confirmed by liquid chromatography-tandem mass spectrometry (LC-MS/MS), using multiple reaction monitoring (MRM). Some digestive and absorbed forms from (Pro-Hyp-Gly)5 were identified as Gly-(Pro-Hyp-Gly)4, (Pro-Hyp-Gly)4, Gly-(Pro-Hyp-Gly)3, (Pro-Hyp-Gly)3, Gly-(Pro-Hyp-Gly)2, and (Pro-Hyp-Gly)2 by MALDI-TOF/MS. The dipeptide hydrolase activity in intestinal mucosa toward Pro-Hyp and Hyp-Gly was extremely low, while Ser-Hyp and Ala-Hyp were substantially hydrolyzed in the cytosol. These results suggest that Hyp-peptides were resistant to intracellular hydrolysis and that a significant amount of these peptides was transported across the intestinal wall and may enter the portal circulation in an intact form.

  为了评估明胶和明胶水解物的消化和同化情况，我们研究了大鼠小肠对典型的含羟脯氨酸二肽 Pro-Hyp、Hyp-Gly、Ser-Hyp Ala-Hyp 和十五肽 (Pro-Hyp-Gly)5 的原位吸收情况。将 Hyp-Gly、Pro-Hyp 和 (Pro-Hyp-Gly)5 注入空肠后进行血管灌流时，灌流液中肽形式的 Hyp（而非游离的 Hyp）逐渐增加。相反，在注射 Ser-Hyp 和 Ala-Hyp 时，游离型和肽型 Hyp 都会迅速增加。通过液相色谱-串联质谱（LC-MS/MS）和多反应监测（MRM）技术证实了灌流液中存在这些二肽和十胜五肽。通过 MALDI-TOF/MS，确定了 (Pro-Hyp-Gly)5 的一些消化和吸收形式，如 Gly-(Pro-Hyp-Gly)4、(Pro-Hyp-Gly)4、Gly-(Pro-Hyp-Gly)3、(Pro-Hyp-Gly)3、Gly-(Pro-Hyp-Gly)2 和 (Pro-Hyp-Gly)2。肠粘膜对 Pro-Hyp 和 Hyp-Gly 的二肽水解酶活性极低，而 Ser-Hyp 和 Ala-Hyp 则在细胞质中被大量水解。这些结果表明，Hyp-肽对细胞内水解具有抗性，大量这些肽通过肠壁运输，并可能以完整的形式进入门静脉循环。
• Studies on Hydroxyproline
  作者：Arthur A. Patchett、Bernhard Witkop

  DOI：10.1021/ja01558a050

  日期：1957.1