γ-L-glutamyl-S-allylthio-L-cysteine | 94504-37-7

• 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: γ-L-glutamyl-S-allylthio-L-cysteine
• 英文别名: gamma-glutamyl-S-allylmercaptocysteine；(2S)-2-amino-5-[[(1R)-1-carboxy-2-(prop-2-enyldisulfanyl)ethyl]amino]-5-oxopentanoic acid
• CAS: 94504-37-7
• 化学式: C₁₁H₁₈N₂O₅S₂
• 分子量: 322.406
• InChiKey: VTEHWEWRSAXLHY-YUMQZZPRSA-N

物化性质

• 沸点：
  612.9±55.0 °C(Predicted)
• 密度：
  1.385±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  180
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  γ-L-glutamyl-S-allylthio-L-cysteine 在 盐酸 作用下， 生成 S-allylmercapto-L-cysteine
  参考文献：
  名称：

  SUGII; SUZUKI; NAGASAWA, Chemical and pharmaceutical bulletin, 1964, vol. 12, p. 1114 - 1115

  摘要：

  DOI：
• 作为产物：
  描述：

  大蒜素 、 L-gamma-谷氨酰-(S)-烯丙基-半胱氨酸 在 garlic protein fraction 作用下， 以 水 为溶剂， 反应 72.0h， 生成 γ-L-glutamyl-S-allylthio-L-cysteine
  参考文献：
  名称：

  Changes of S-Allylmercaptocysteine and γ-Glutamyl-S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process

  摘要：

  gamma-Glutamyl-S-allylmercaptocysteine (GSAMC), a putative precursor compound of S-allylmercaptocysteine (SAMC), was isolated and identified from aged garlic extract (AGE). We analyzed the change of their contents in AGE during the aging process, chronologically from 1 to 22 months. The formation of these compounds occurred mostly during the early stage of the aging period: the SAMC content reached a maximum at approximately 4 months, whereas the GSAMC content reached a maximum at 1 month and then decreased during the subsequent aging period. To assess the possible relationship between the change of the two compounds during the aging process, we set up the model reactions with the hypothesis that GSAMC is produced from gamma-glutamyl-S-allylcysteine (GSAC)/gamma-gultamyl-S-1-propenylcysteine (GS1PC) and that SAMC is produced from GSAMC by endogenous gamma-glutamyl transpeptidase (GGT) in garlic during the early stage of the aging process. We found that, in the model reactions, SAMC was produced from GSAMC by the garlic protein fraction having GGT activity and its production was suppressed by a GGT inhibitor. Furthermore, the production of GSAMC from allicin and GSAC/GS1PC was found in another model reaction. The reaction between allicin and GS1PC was faster than that between allicin and GSAC and, thus, may be involved in the production of GSAMC in the early stage of the aging process.

  DOI：

  10.1021/acs.jafc.8b02541

文献信息

• Changes of <i>S</i>-Allylmercaptocysteine and γ-Glutamyl-<i>S</i>-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process
  作者：Takuto Fujii、Toshiaki Matsutomo、Yukihiro Kodera

  DOI：10.1021/acs.jafc.8b02541

  日期：2018.10.10

  gamma-Glutamyl-S-allylmercaptocysteine (GSAMC), a putative precursor compound of S-allylmercaptocysteine (SAMC), was isolated and identified from aged garlic extract (AGE). We analyzed the change of their contents in AGE during the aging process, chronologically from 1 to 22 months. The formation of these compounds occurred mostly during the early stage of the aging period: the SAMC content reached a maximum at approximately 4 months, whereas the GSAMC content reached a maximum at 1 month and then decreased during the subsequent aging period. To assess the possible relationship between the change of the two compounds during the aging process, we set up the model reactions with the hypothesis that GSAMC is produced from gamma-glutamyl-S-allylcysteine (GSAC)/gamma-gultamyl-S-1-propenylcysteine (GS1PC) and that SAMC is produced from GSAMC by endogenous gamma-glutamyl transpeptidase (GGT) in garlic during the early stage of the aging process. We found that, in the model reactions, SAMC was produced from GSAMC by the garlic protein fraction having GGT activity and its production was suppressed by a GGT inhibitor. Furthermore, the production of GSAMC from allicin and GSAC/GS1PC was found in another model reaction. The reaction between allicin and GS1PC was faster than that between allicin and GSAC and, thus, may be involved in the production of GSAMC in the early stage of the aging process.
• SUGII; SUZUKI; NAGASAWA, Chemical and pharmaceutical bulletin, 1964, vol. 12, p. 1114 - 1115
  作者：SUGII、SUZUKI、NAGASAWA、KAWASHIMA

  DOI：——

  日期：——