N-γ-glutamyl-boletine | 474766-43-3

• 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: N-γ-glutamyl-boletine
• 英文别名: γ-glutamyl boletine；N-gamma-glutamyl-boletine；(2S)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-6-oxodecanoic acid
• CAS: 474766-43-3
• 化学式: C₁₅H₂₆N₂O₆
• 分子量: 330.381
• InChiKey: YKKFSDKZBGDWDC-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  23
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-γ-glutamyl-boletine 在 盐酸 、 水 作用下， 生成 L-谷氨酸 、
  参考文献：
  名称：

  A novel dipeptide, N-γ-glutamyl boletine, and a cyclic iminium toxin from the mushroom Tylopilus sp. (Boletaceae)

  摘要：

  N-gamma-Glutamyl boletine and a toxin, 2-buty1-1-azacyclohexene iminium salt, were isolated from the mushroom Tylopilus sp. (Boltaceae). The absolute stereostructure of N-gamma-glutamyl boletine was clarified based on spectroscopic analysis, acidic hydrolysis and total synthesis. N-gamma-Glutamyl boletine exhibited moderate antibacterial activity. 2-Buty1-1-azacyclohexene iminium salt exhibited moderate acute toxicity against ddY mice. We proposed feasible biosynthetic pathway of piperidine alkaloids that the cyclic imimum compound might be biosynthesized from boletine, a new amino acid containing an delta-amino ketone moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01495-8
• 作为产物：
  描述：

  (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester 在 palladium dihydroxide WSCD-HCl 、 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 N-γ-glutamyl-boletine
  参考文献：
  名称：

  A novel dipeptide, N-γ-glutamyl boletine, and a cyclic iminium toxin from the mushroom Tylopilus sp. (Boletaceae)

  摘要：

  N-gamma-Glutamyl boletine and a toxin, 2-buty1-1-azacyclohexene iminium salt, were isolated from the mushroom Tylopilus sp. (Boltaceae). The absolute stereostructure of N-gamma-glutamyl boletine was clarified based on spectroscopic analysis, acidic hydrolysis and total synthesis. N-gamma-Glutamyl boletine exhibited moderate antibacterial activity. 2-Buty1-1-azacyclohexene iminium salt exhibited moderate acute toxicity against ddY mice. We proposed feasible biosynthetic pathway of piperidine alkaloids that the cyclic imimum compound might be biosynthesized from boletine, a new amino acid containing an delta-amino ketone moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01495-8

文献信息

• Diastereotopos-differentiating allylic alkylation as a key step in the synthesis of γ-glutamyl boletine
  作者：Dnyaneshwar Gawas、Uli Kazmaier

  DOI：10.1039/b917589j

  日期：——

  γ-glutamyl boletine is described, based on a diastereotopos-differentiating allylic alkylation of chelated amino acid ester enolates. Independent of the configuration of the leaving group in the allylic substrate, the allylation product is obtained as a single stereoisomer. Its configuration is solely controlled by the stereogenic center adjacent to the π-allyl complex formed.

  直截了当的方法 γ-谷氨酰胺基于螯合的氨基酸酯烯醇化物的非对映异构性-烯丙基烷基化，描述了牛磺酸。与烯丙基底物中离去基团的构型无关，烯丙基化产物以单一立体异构体的形式获得。它的构型由与形成的π-烯丙基复合物相邻的立体中心单独控制。