mycosporine glycine | 65318-21-0

• 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: mycosporine glycine
• 英文别名: Mycosporin-Gly；2-[[(5S)-5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohexen-1-yl]amino]acetic acid
• CAS: 65318-21-0
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: XZQILKYKJYHEHD-JTQLQIEISA-N

物化性质

• 沸点：
  524.9±50.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 mycosporine glycine 生成 Mycosporin-gly methyl ester
  参考文献：
  名称：

  霉菌孢素的合成和绝对构型。施陶丁格反应的新应用

  摘要：

  描述 sommaire du protocole 实验渗透剂 de synthetiser des mycosporines; Eude cristallographique de leur 配置；使用de la反应de Stander

  DOI：

  10.1021/ja00206a059
• 作为产物：
  描述：

  (1S,3R,4R,5R)-3,4-O-Benzylidene-1,3,4-trihydroxy-6-oxabicyclo<3.2.1>octan-7-one 在 palladium on activated charcoal 、 lithium chloride sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 氢气 、 sodium acetate 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 对甲苯磺酸 、 pyridinium chlorochromate 、 三氟乙酸 作用下， 以 四氯化碳 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.63h， 生成 mycosporine glycine
  参考文献：
  名称：

  霉菌孢素的合成和绝对构型。施陶丁格反应的新应用

  摘要：

  描述 sommaire du protocole 实验渗透剂 de synthetiser des mycosporines; Eude cristallographique de leur 配置；使用de la反应de Stander

  DOI：

  10.1021/ja00206a059

文献信息

• Method for producing mycosporine-like amino acid using microbes
  申请人：THE KITASATO INSTITUTE

  公开号：US10307356B2

  公开（公告）日：2019-06-04

  Provided are: a method for producing a mycrosporine-like amino acid (MAA) that includes a step in which microbes are cultivated that produce MAA on the outside of bacterial cells, a step in which the bacterial cells and extracellular culture fluid are separated, and a step in which the MAA is recovered from the extracellular culture fluid; an MAA indicated by formula (1), an MAA produced using this method, or an ultraviolet-absorbing composition including the MAA indicated by formula (1); and a composition including the MAA produced using this method or the MAA indicated by formula (1), for preventing at least one symptom or disease selected from a group comprising acute skin reactions, aging of the skin, and skin cancer.

  提供了一种生产霉菌孢子样氨基酸（MAA）的方法，该方法包括培养在细菌细胞外产生 MAA 的微生物的步骤，分离细菌细胞和细胞外培养液的步骤，以及从细胞外培养液中回收 MAA 的步骤；式（1）所示的 MAA、用该方法生产的 MAA 或包括式（1）所示的 MAA 的紫外线吸收组合物；以及包括用该方法生产的 MAA 或式（1）所示的 MAA 的组合物，用于预防至少一种选自急性皮肤反应、皮肤老化和皮肤癌的症状或疾病。
• Transformations of Quinic Acid. Asymmetric Synthesis and Absolute Configuration of Mycosporin I and Mycosporin-gly
  作者：James D. White、Janice H. Cammack、Kazuhiko Sakuma、Gordon W. Rewcastle、Rexford K. Widener

  DOI：10.1021/jo00117a008

  日期：1995.6

  D-(-)-Quinic acid (1) was converted to the fungal metabolites mycosporin I (2) and mycosporin-gly (13) via the iminophosphorane 64. The latter was prepared in 10 steps from 1 using oxidative bromination of quinide 33 to furnish 41. Reduction of the gamma-lactone, followed by protection of the 1,2-diol, was accompanied by migration of the benzoyl group to yield 43. The latter was oxidized to 47 which underwent displacement by sulfinate to give 59. O-Methylation, followed by reduction of the benzoate, afforded 61. Oxidation of 61 produced 62 which was converted to beta-azido enone 63. Treatment of 63 with triphenylphosphine gave crystalline 64. An aza-Wittig reaction of 64 with glyoxylate and reduction of the resultant imine yielded 68 which, after deprotection, afforded 13. Analogous coupling of 64 with diethyl ketomalonate and subsequent reduction of the ester groups led to 2. Mycosporin I and mycosporin-gly are shown by this sequence to possess S absolute configuration.
• WHITE, JAMES D.;CAMMACK, JANICE H.;SAKUMA, KAZUHIKO, J. AMER. CHEM. SOC., 111,(1989) N4, C. 8970-8972
  作者：WHITE, JAMES D.、CAMMACK, JANICE H.、SAKUMA, KAZUHIKO

  DOI：——

  日期：——
• METHOD FOR PRODUCING MYCOSPORINE-LIKE AMINO ACID USING MICROBES
  申请人：THE KITASATO INSTITUTE

  公开号：US20170202762A1

  公开（公告）日：2017-07-20

  Provided are: a method for producing a mycrosporine-like amino acid (MAA) that includes a step in which microbes are cultivated that produce MAA on the outside of bacterial cells, a step in which the bacterial cells and extracellular culture fluid are separated, and a step in which the MAA is recovered from the extracellular culture fluid; an MAA indicated by formula (1), an MAA produced using this method, or an ultraviolet-absorbing composition including the MAA indicated by formula (1); and a composition including the MAA produced using this method or the MAA indicated by formula (1), for preventing at least one symptom or disease selected from a group comprising acute skin reactions, aging of the skin, and skin cancer.