N-((9-Fluorenylmethoxy)carbonyl)-O-(carboxymethyl)-L-serine δ-allyl diester | 133486-74-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-((9-Fluorenylmethoxy)carbonyl)-O-(carboxymethyl)-L-serine δ-allyl diester
• 英文别名: N-[(9-Fluorenylmethoxy)carbonyl]-O-(carboxymethyl)-L-serine δ-allyl diester；(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-oxo-2-prop-2-enoxyethoxy)propanoic acid
• CAS: 133486-74-5
• 化学式: C₂₃H₂₃NO₇
• 分子量: 425.438
• InChiKey: JGHQOGOYZHRBON-FQEVSTJZSA-N

物化性质

• 沸点：
  666.2±55.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-Boc-L-缬氨酸 、 N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 Boc-L-天冬氨酸-4-环己酯 、 N-((9-Fluorenylmethoxy)carbonyl)-O-(carboxymethyl)-L-serine δ-allyl diester 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (3S,6S,12S,15S)-6-Carboxymethyl-12-(3-guanidino-propyl)-15-isopropyl-5,8,11,14,17-pentaoxo-1-oxa-4,7,10,13,16-pentaaza-cyclooctadecane-3-carboxylic acid
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013
• 作为产物：
  描述：

  N-((9-Fluorenylmethoxy)carbonyl)-O-(carboxymethyl)-L-serine α-tert-butyl δ-allyl diester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以93%的产率得到N-((9-Fluorenylmethoxy)carbonyl)-O-(carboxymethyl)-L-serine δ-allyl diester
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013

文献信息

• [EN] CHIMERIC AMINO ACIDS AND PEPTIDES CONTAINING THESE ANALOGUES
  申请人：GENENTECH, INC.

  公开号：WO1991004247A1

  公开（公告）日：1991-04-04

  (EN) A chimeric amino acid analogue is provided suitable for incorporating into peptides which compound is represented by formula (1) where P1 and P2 are preferably an amine protecting agents, or P2 may be a protected aminoiminomethyl group, n is 1 and X can be OH, halide, or preferably an activating group suitable for conjugating the compound of formula (1) to a peptide by conventional means. Peptides containing the chimeric amino acid analogue are provided and include a platelet-aggregation inhibitor represented by Aaa1-Cpd1-Gly-Asp-Aaa2 where Aaa1 is Gly or H, Cpd1 is the compound of formula (1) which has been deprotected and Aaa2 is a hydrophobic amino acid, preferably Val. Alternatively, Aaa1 and Aaa2 may be linked through a structure to form a cycle.(FR) Un analogue d'acide aminé chimérique est approprié pour être incorporé dans des peptides et est représenté par la formule (1) dans laquelle P1 et P2 sont de préférence des agents de protection d'amine, ou P2 peut être un groupe aminoiminométhyle protégé, n vaut 1 et X peut être OH, un halogénure ou de préférence un groupe d'activation approprié pour conjuguer le composé de formule (1) avec un peptide par des moyens conventionnels. Des peptides contenant l'analogue d'acide aminé chimérique sont obtenus et contiennent un inhibiteur d'agrégation de plaquettes représenté par Aaa1-Cpd1-Gly-Asp-Aaa2, où Aaa1 représente Gly ou H, Cpd1 est le composé de formule (1) dont la protection a été enlevée et Aaa2 est un acide aminé hydrophobe, de préférence Val. Dans une variante, Aaa1 et Aaa2 peuvent être reliés par l'intermédiaire d'une structure pour former un cycle.

  一个合成了含有共价修饰的氨基酸类似体的结构，可与第(1)式表示的复合物结合，其中式(1)中的P1和P2可为胺保护剂，或P2为受保护的氨基-甲基酰胺基团，n＝1，且X可以是OH、卤代化合物或最好是非Michael亲核结合位点的活性基团。含有该氨基酸类似体的肽可获得，其中含有血小板聚集抑制剂Aaa1-Cpd1-Gly-Asp-Aaa2，在这种情况下，Aaa1代表Gly或H，Cpd1代表式(1)中的相应产物（已解封）、Aaa2为疏水氨基酸，最好为甲硫氨酸(Vall)。另一种情况中，Aaa1和Aaa2通过结构相互连接，以形成一个环状结构。
• SMALL CYCLIC PLATELET AGGREGATION INHIBITORS
  申请人：GENENTECH, INC.

  公开号：EP0482080B1

  公开（公告）日：1997-03-26
• CHIMERIC AMINO ACIDS AND PEPTIDES CONTAINING THESE ANALOGUES
  申请人：GENENTECH, INC.

  公开号：EP0493506A1

  公开（公告）日：1992-07-08
• [EN] SMALL CYCLIC PLATELET AGGREGATION INHIBITORS
  申请人：GENENTECH, INC.

  公开号：WO1991001331A1

  公开（公告）日：1991-02-07

  (EN) A platelet aggregation inhibitor useful as an antithrombotic is provided which consists of a synthetic cyclic pentapeptide containing the tripeptide sequence Arg-Gly-Asp and a thioether linkage in the cycle. A preferred platelet aggregation inhibitor is represented by formula (I), where R1 and R9 are OH; R2, R4, R5, R6, R7, R8 and R14 are hydrogen; R3 and R4 are joined to form a pyrrolidine ring; X is sulfur; m is 1 and n is 3.(FR) L'inhibiteur d'aggrégation de plaquettes décrit, qui est utile comme agent antithrombose, se compose d'un pentapeptide cyclique synthétique contenant la séquence tripeptidique Arg-Gly-Asp et une liaison thioéther dans le cycle. Un inhibiteur d'aggrégation de plaquettes préféré est représenté par la formule: (I), où R1 et R9 représentent OH; R2, R4, R5, R6, R7, R8 et R14 représentent l'hydrogène; R3 et R4 sont joints pour former une chaîne fermée de pyrrolidine; X représente le soufre; m est égal à 1; et n est égal à 3.
• Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis
  作者：Mark S. Stanley

  DOI：10.1021/jo00050a013

  日期：1992.11

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.