(2S,4R)-4-氨基甲基-1-N-叔丁氧羰基吡咯烷-2-甲酸 | 132622-72-1

• 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: (2S,4R)-4-氨基甲基-1-N-叔丁氧羰基吡咯烷-2-甲酸
• 中文别名: (2S,4R)-4-氨基甲酸-1,2-吡咯烷二羧酸-1-(1,1-二甲基乙基)酯
• 英文名称: (4S)-1-(tert-butoxycarbonyl)-4-(aminomethyl)-L-proline
• 英文别名: (4R)-N-Boc-4-(aminomethyl)-L-proline；(4R)-1-(tert-Butoxycarbonyl)-4-(aminomethyl)-L-proline；(2S,4R)-4-(azaniumylmethyl)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylate
• CAS: 132622-72-1
• 化学式: C₁₁H₂₀N₂O₄
• 分子量: 244.291
• InChiKey: VWFCKAANOBELKO-SFYZADRCSA-N

物化性质

• 沸点：
  389.0±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-氨基甲基-1-N-叔丁氧羰基吡咯烷-2-甲酸 在 sodium hydroxide 、 氨 、 silver nitrate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 30.0h， 生成 (4S)-1-(tert-butoxycarbonyl)-4-<<<<(p-toluenesulfonyl)imino>aminomethyl>amino>methyl>-L-proline
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016
• 作为产物：
  描述：

  (2S,4R)-4-Methanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 22.0~55.0 ℃ 、3.1 MPa 条件下， 反应 87.0h， 生成 (2S,4R)-4-氨基甲基-1-N-叔丁氧羰基吡咯烷-2-甲酸
  参考文献：
  名称：

  Conformationally restricted arginine analogs

  摘要：

  We report the practical synthesis and structural characterization of a set of conformationally constrained protected arginine analogues. These enantiomerically pure analogues have the general structure 1 and are prepared in seven to eight steps from the commercially available isomers of 4-hydroxyproline. These analogues vary in side chain length and in relative and absolute stereochemistry and are suitable for the direct introduction into peptides. The resulting peptide analogues should be useful as enzymatically stable replacements for bioactive peptides and as probes for understanding the conformational aspects of protein-peptide interactions.

  DOI：

  10.1021/jo00009a016

文献信息

• Chimeric amino acid analogues
  申请人：Genentech, Inc.

  公开号：US05120859A1

  公开（公告）日：1992-06-09

  A chimeric amino acid analogue is provided suitable for incorporating into peptides which compound is represented by Formula 1: ##STR1## where P.sub.1 is preferably an amine protecting agent, and P.sub.2 and P.sub.3 are preferably amine or guanidine protecting agents. X can be OH, halide, or preferably an activating group suitable for conjugating the compound of Formula 1 to a peptide by conventional means, and m and n are 0-1 and 0-2 respectively. Peptides containing the chimeric amino acid analog are provided and include a platelet-aggregation inhibitor represented by Aaa.sub.1 -CPdl-Gly-Asp-Aaa.sub.2 where Aaa.sub.1 is Gly or H, Cpdl is the compound of Formula 1 which has been deprotected and Aaa.sub.2 is a hydrophobic amino acid preferably Val.

  提供了一种适合用于合成肽中的嵌合氨基酸类似物，该化合物由以下式表示：##STR1## 其中P.sub.1 最好是氨基保护剂，P.sub.2 和P.sub.3 最好是氨基或胍啉保护剂。X 可以是OH、卤素，或者最好是适合通过常规手段与Formula 1化合物结合的活化基团，m 和n 分别为0-1和0-2。提供了含有嵌合氨基酸类似物的肽，并包括一个由Aaa.sub.1 -CPdl-Gly-Asp-Aaa.sub.2 表示的血小板聚集抑制剂，其中Aaa.sub.1 是Gly或H，Cpdl 是已去保护的Formula 1化合物，Aaa.sub.2 是一个疏水性氨基酸，最好是Val。
• [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。
• Peptidomimetics of Arg-Phe-NH2 as small molecule agonists of Mas-related gene C (MrgC) receptors
  作者：Niyada Hin、Jesse Alt、Sarah C. Zimmermann、Greg Delahanty、Dana V. Ferraris、Camilo Rojas、Fengxian Li、Qin Liu、Xinzhong Dong、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmc.2014.09.025

  日期：2014.11

  A series of Arg-Phe-NH2 peptidomimetics containing an Arg mimetic were synthesized and tested as agonists of human MrgX1, rat MrgC, and mouse MrgC11 receptors. As predicted from the previously established species specificity, these peptidomimetics were found to be devoid of MrgX1 agonist activity. In contrast, these compounds acted as agonists of MrgC and/or MrgC11 with varying degrees of potency. These new peptidomimetics should complement the existing small molecule human MrgX1 agonists and enhance our ability to assess the therapeutic utility of targeting Mrg receptors in rodent models. (C) 2014 Elsevier Ltd. All rights reserved.
• 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
• US5120859A
  申请人：——

  公开号：US5120859A

  公开（公告）日：1992-06-09