(3S)-3-甲氧基-L-天冬氨酸 | 316172-74-4

• 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
• 中文名称: (3S)-3-甲氧基-L-天冬氨酸
• 英文名称: L-threo-β-methoxyaspartate
• 英文别名: (3S)-3-methoxy-L-aspartic acid；(2S, 3S)-3-Amino-2-methoxy-pentanedioic acid；(2S,3S)-2-amino-3-methoxybutanedioic acid
• CAS: 316172-74-4
• 化学式: C₅H₉NO₅
• 分子量: 163.13
• InChiKey: FDQLAEMVGNHRBH-HRFVKAFMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-3-甲氧基-L-天冬氨酸 在 氢氧化钾 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 2.0h， 生成 DL-threo-3-Methoxy-N-benzyloxycarbonyl-asparaginsaeure-dimethylester
  参考文献：
  名称：

  Complete Stereochemistry of Neamphamide A and Absolute Configuration of the β-Methoxytyrosine Residue in Papuamide B

  摘要：

  [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.

  DOI：

  10.1021/jo0508853
• 作为产物：
  描述：

  在 二乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3S)-3-甲氧基-L-天冬氨酸
  参考文献：
  名称：

  抗生素A54145的总合成和结构建立/修订。

  摘要：

  A54145是一类结构类似于达托霉素的抗菌环脂肽家族。自1990年被发现以来，仅报道了甲氧基天冬氨酸（MeO-Asp）和羟基天冬酰胺（HO-Asn）的歧义结构。我们已经开发出有效的路线，以获得充分的保护升-MeO-Asp和升-总部-ASN建设与Fmoc-SPPS兼容块，这使我们能够建立其结构，由A54145的全合成升-3小号- HO-Asn和l -3 R -MeO-Asp，修改了错误提出的l -3 S -MeO-Asp结构。

  DOI：

  10.1021/acs.orglett.9b01972

文献信息

• Syntheses of optically pure β-hydroxyaspartate derivatives as glutamate transporter blockers
  作者：Keiko Shimamoto、Yasushi Shigeri、Yoshimi Yasuda-Kamatani、Bruno Lebrun、Noboru Yumoto、Terumi Nakajima

  DOI：10.1016/s0960-894x(00)00487-x

  日期：2000.11

  serves as an indispensable tool for the investigation of the physiological roles of the transporters. To examine the precise interaction between a blocker and the transporters, we synthesized the optically pure isomers (L- and D-TBOA) and its erythro-isomers. L-TBOA is the most potent blocker for the human excitatory amino acid transporters (EAAT1-3), while D-TBOA revealed a difference in the pharmacophores

  DL-苏-β-苄氧基天冬氨酸（DL-TBOA）是谷氨酸转运蛋白的不可转运的阻滞剂，它是研究转运蛋白的生理作用必不可少的工具。为了检查阻滞剂和转运蛋白之间的精确相互作用，我们合成了光学纯的异构体（L-和D-TBOA）及其赤型异构体。L-TBOA是人类兴奋性氨基酸转运蛋白（EAAT1-3）的最有效阻滞剂，而D-TBOA显示出EAAT1和EAAT3之间的药效基团有所不同。我们还合成了L-TBOA的取代基变体（甲基或萘基甲基衍生物）。此处获得的结果表明，庞大的取代基对于不可运输的阻滞剂至关重要。
• 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.
• 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.
• Total Synthesis and Structural Establishment/Revision of Antibiotics A54145
  作者：Delin Chen、Hoi Yee Chow、Kathy Hiu Laam Po、Wenjie Ma、Emily Lok Yee Leung、Zhenquan Sun、Ming Liu、Sheng Chen、Xuechen Li

  DOI：10.1021/acs.orglett.9b01972

  日期：2019.7.19

  and the hydroxy-asparagine (HO-Asn) have been reported. We have developed efficient routes to obtain the fully protected l-MeO-Asp and l-HO-Asn building blocks compatible with Fmoc-SPPS, and a total synthesis of A54145 that enabled us to establish its structure, consisting of l-3S-HO-Asn and l-3R-MeO-Asp, revising the wrongly proposed structure of l-3S-MeO-Asp.

  A54145是一类结构类似于达托霉素的抗菌环脂肽家族。自1990年被发现以来，仅报道了甲氧基天冬氨酸（MeO-Asp）和羟基天冬酰胺（HO-Asn）的歧义结构。我们已经开发出有效的路线，以获得充分的保护升-MeO-Asp和升-总部-ASN建设与Fmoc-SPPS兼容块，这使我们能够建立其结构，由A54145的全合成升-3小号- HO-Asn和l -3 R -MeO-Asp，修改了错误提出的l -3 S -MeO-Asp结构。