(2S,3R)-β-methoxytyrosine | 700816-76-8

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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: (2S,3R)-β-methoxytyrosine
• 英文别名: (R)-β-methoxy-L-tyrosine；(2S,3R)-3-methoxytyrosine；(2S,3R)-2-amino-3-(4-hydroxyphenyl)-3-methoxypropanoic acid
• CAS: 700816-76-8
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: GGCZGJOSDPRIIM-DTWKUNHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R)-β-methoxytyrosine 在 氧气 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 (3S)-3-甲氧基-L-天冬氨酸
  参考文献：
  名称：

  Concise Synthesis of All Stereoisomers of β-Methoxytyrosine and Determination of the Absolute Configuration of the Residue in Callipeltin A

  摘要：

  All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.

  DOI：

  10.1021/ol0513600
• 作为产物：
  描述：

  L-酪氨酸甲酯 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 silver trifluoromethanesulfonate 、 N,N-二异丙基乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 (2S,3R)-β-methoxytyrosine
  参考文献：
  名称：

  Concise Synthesis of All Stereoisomers of β-Methoxytyrosine and Determination of the Absolute Configuration of the Residue in Callipeltin A

  摘要：

  All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.

  DOI：

  10.1021/ol0513600

文献信息

• Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B
  作者：Naoya Oku、Ravi Krishnamoorthy、Alan G. Benson、Robert L. Ferguson、Mark A. Lipton、Lawrence R. Phillips、Kirk R. Gustafson、James B. McMahon

  DOI：10.1021/jo0508853

  日期：2005.8.1

  [GRAPHICS]The absolute stereochemistry of the three unresolved structural components in neamphamide A (1) was determined to be (R)-beta-methoxy-L-tyrosine, (2R,3R,4S)-4-amino-7-guanidino-2,3-dihydroxyheptanoic acid, and (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid. Stereochemical assignments were made by chemical degradation of 1, derivatization of the resulting products, and then spectroscopic and chromatographic comparison of the derivatives with synthetically prepared standards. Using the same analytical protocol developed for 1, the beta-methoxytyrosine residue in papuamide B (2) was found to be (R)-beta-methoxy-D-tyrosine. This represents a rare example of divergent stereochemistry in an unusual amino acid residue that is present in two closely related classes of peptides.
• Concise Synthesis of All Stereoisomers of β-Methoxytyrosine and Determination of the Absolute Configuration of the Residue in Callipeltin A
  作者：Angela Zampella、Rosa D'Orsi、Valentina Sepe、Agostino Casapullo、Maria Chiara Monti、Maria Valeria D'Auria

  DOI：10.1021/ol0513600

  日期：2005.8.1

  All stereoisomers of beta-methoxytyrosine (beta-OMeTyr), a stereo-undefined component of callipeltin A, were synthesized from L- and D-tyrosine. The stereochemistry of beta-OMeTyr in callipeltin A was determined to be 2R,3R by an oxidative procedure and Marfey's analysis.