(3R)-3-methoxy-L-aspartic acid | 863871-25-4

• 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
• 英文名称: (3R)-3-methoxy-L-aspartic acid
• 英文别名: (2S,3R)-2-amino-3-methoxybutanedioic acid
• CAS: 863871-25-4
• 化学式: C₅H₉NO₅
• 分子量: 163.13
• InChiKey: FDQLAEMVGNHRBH-STHAYSLISA-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：

  (3R)-3-methoxy-L-aspartic acid 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 dimethyl (3R)-N-[(benzyloxy)carbonyl]-3-methoxy-L-aspartate
  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：

  (2S,3R)-diethyl 2-amino-3-methoxysuccinate 在 盐酸 作用下， 以 水 为溶剂， 以1.69 g的产率得到(3R)-3-methoxy-L-aspartic acid
  参考文献：
  名称：

  Cytobactamids的总合成和Cytobactamid 919-2的结构确认

  摘要：

  描述了新型细菌IIa型拓扑异构酶抑制剂胱霉酰胺919-2的聚合全合成。该合成证实了先前提出的相对构型并建立了这种不寻常肽的绝对构型。

  DOI：

  10.1002/anie.201705387

文献信息

• 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。
• 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.