N-tert-butoxycarbonyl-TAN-950 A | 127608-01-9

• 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-tert-butoxycarbonyl-TAN-950 A
• 英文别名: N-Boc TAN-950 A；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(5-oxo-2H-1,2-oxazol-4-yl)propanoic acid
• CAS: 127608-01-9
• 化学式: C₁₁H₁₆N₂O₆
• 分子量: 272.258
• InChiKey: NEJZEXLCUVPAHW-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.49
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  121.63
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-TAN-950 A 在 三氟乙酸 作用下， 反应 30.0h， 生成 TAN 950A
  参考文献：
  名称：

  A novel amino acid antibiotic tan-950

  摘要：

  A novel antifungal antibiotic, TAN-950 A, was isolated from the culture filtrate of Streptomyces platensis A-136. Its structure was determined to be (S)-2-amino-3-(isoxazolin-5-on-4-yl)-propanoic acid. Minor components, TAN-950 B, C, D and E, were found to be present in an equilibrium mixture containing TAN-950 A. Their structures were determined from spectral analyses, X-ray crystallographic analysis and synthesis from L-glutamic acid.

  DOI：

  10.1016/s0040-4020(01)91004-x
• 作为产物：
  描述：

  methyl (2R)-1-tert-butoxycarbonyl-4-formylpyroglutamate 在 sodium hydroxide 、 盐酸羟胺 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 N-tert-butoxycarbonyl-TAN-950 A
  参考文献：
  名称：

  A novel amino acid antibiotic tan-950

  摘要：

  A novel antifungal antibiotic, TAN-950 A, was isolated from the culture filtrate of Streptomyces platensis A-136. Its structure was determined to be (S)-2-amino-3-(isoxazolin-5-on-4-yl)-propanoic acid. Minor components, TAN-950 B, C, D and E, were found to be present in an equilibrium mixture containing TAN-950 A. Their structures were determined from spectral analyses, X-ray crystallographic analysis and synthesis from L-glutamic acid.

  DOI：

  10.1016/s0040-4020(01)91004-x

文献信息

• Synthesis and Biological Activity of (S)-2-Amino-3(2,5-dihydro-5-oxo-4-isoxazolyl)propanoic Acid (TAN-950 A) Derivatives.
  作者：Norikazu TAMURA、Yoshihiro MATSUSHITA、Toshi IWAMA、Setsuo HARADA、Shoji KISHIMOTO、Katsumi ITOH

  DOI：10.1248/cpb.39.1199

  日期：——

  starting with methyl (S)- and (R)-N-Boc-pyroglutamate (8) via acylation at the C-4 position followed by isoxazolone formation with hydroxylamine and subsequent deprotection reactions. The lactam 16, prepared from (RS)-aminoadipic acid, and dimethyl esters 19 of (R)- and (S)-aspartic acid were converted to (RS)-3-methyl-homo-TAN-950 A (15i) and optically active nor-TAN-950 A derivatives 15j--o, respectively

  （S）-2-氨基-3-（2,5-二氢-5-氧代-4-异恶唑基）丙酸（TAN-950 A（1））是一种新型氨基酸抗生素，对谷氨酸受体具有高亲和力中枢神经系统。为了提高对谷氨酸受体的亲和力，研究了TAN-950 A衍生物6a-o，15a-o的构效关系。以（S）-和（R）-N-Boc-焦谷氨酸甲酯（8）为起始原料，通过C-4位的酰化反应合成旋光性TAN-950 A类似物15a-h，然后与羟胺形成异恶唑酮并随后脱保护反应。将由（RS）-氨基己二酸和（R）-和（S）-天冬氨酸的二甲酯19制备的内酰胺16转化为（RS）-3-甲基-homo-TAN-950 A（15i）和利用相似的反应序列分别对光学活性的nor-TAN-950 A衍生物15j-o进行了研究。大多数TAN-950 A衍生物6a-o，15a-o对谷氨酸受体具有亲和力。3-烷基衍生物15b，d-g特别显示出对喹喹啉亚型受体的高亲和力，并对海马