endolide D

• 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: endolide D
• 英文别名: Endolide D；(3S,6S,9S,12S)-3-benzyl-6,12-bis(furan-3-ylmethyl)-1,7-dimethyl-9-propan-2-yl-1,4,7,10-tetrazacyclododecane-2,5,8,11-tetrone
• 化学式: C₃₀H₃₆N₄O₆
• 分子量: 548.639
• InChiKey: AJCBJCMHGIPZHI-CQJMVLFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  endolide D 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 16.67h， 生成 L-Phe-L-FDAA 、 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)-3-methylbutanoic acid
  参考文献：
  名称：

  Insights into the Biosynthetic Origin of 3-(3-Furyl)alanine in Stachylidium sp. 293 K04 Tetrapeptides

  摘要：

  The marine-sponge-derived fungus Stachylidium sp. 293 K04 produces the N-methylated peptides endolide A (1) and endolide B (2), showing affinity for the vasopressin receptor 1A and serotonin receptor 5HT(2B), respectively. Both peptides feature the rare amino acid 3-(3-furyl)alanine. Isotope labeling experiments, employing several C-13-enriched precursors, revealed that this unprecedented heterocyclic amino acid moiety in endolide A (1) is synthesized from a cyclic intermediate of the shikimate pathway, but not from phenylalanine. Two new tetrapeptide analogues, endolides C and D (3 and 4), were characterized, as well as the previously described hirsutide (5).

  DOI：

  10.1021/acs.jnatprod.6b00601

文献信息

• Insights into the Biosynthetic Origin of 3-(3-Furyl)alanine in <i>Stachylidium</i> sp. 293 K04 Tetrapeptides
  作者：Fayrouz El Maddah、Stefan Kehraus、Mamona Nazir、Celso Almeida、Gabriele M. König

  DOI：10.1021/acs.jnatprod.6b00601

  日期：2016.11.23

  The marine-sponge-derived fungus Stachylidium sp. 293 K04 produces the N-methylated peptides endolide A (1) and endolide B (2), showing affinity for the vasopressin receptor 1A and serotonin receptor 5HT(2B), respectively. Both peptides feature the rare amino acid 3-(3-furyl)alanine. Isotope labeling experiments, employing several C-13-enriched precursors, revealed that this unprecedented heterocyclic amino acid moiety in endolide A (1) is synthesized from a cyclic intermediate of the shikimate pathway, but not from phenylalanine. Two new tetrapeptide analogues, endolides C and D (3 and 4), were characterized, as well as the previously described hirsutide (5).