(2R,4S)-1-BOC-4-氨基-吡咯烷-2-羧酸 | 132622-78-7

• 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: (2R,4S)-1-BOC-4-氨基-吡咯烷-2-羧酸
• 中文别名: (2R,4S)-4-氨基-1,2-吡咯烷二羧酸1-叔丁酯
• 英文名称: (4S)-1-(tert-butoxycarbonyl)-4-amino-D-proline
• 英文别名: (4S)-4-amino-1-(tert-butoxycarbonyl)-D-proline；(2R,4S)-4-amino-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid；(2R,4S)-4-azaniumyl-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylate
• CAS: 132622-78-7
• 化学式: C₁₀H₁₈N₂O₄
• 分子量: 230.264
• InChiKey: WDWRIVZIPSHUOR-NKWVEPMBSA-N

物化性质

• 沸点：
  371.1±42.0 °C(Predicted)
• 密度：
  1.232

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (2R,4S)-1-BOC-4-氨基-吡咯烷-2-羧酸 在 劳森试剂 、 碳酸氢钠 、 sodium carbonate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 二乙胺 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.34h， 生成 (4S)-1-methyl-N-{(3S,5R)-5-[4-(methylcarbamoyl)-1,3-thiazol-2-yl]-1-[4-(1H-tetrazol-5-yl)benzoyl]pyrrolidin-3-yl}-2,6-dioxo-1,3-diazinane-4-carboxamide
  参考文献：
  名称：

  Characterization of Specific N-α-Acetyltransferase 50 (Naa50) Inhibitors Identified Using a DNA Encoded Library

  摘要：

  Two novel compounds were identified as Naa50 binders/inhibitors using DNA-encoded technology screening. Biophysical and biochemical data as well as cocrystal structures were obtained for both compounds (3a and 4a) to understand their mechanism of action. These data were also used to rationalize the binding affinity differences observed between the two compounds and a MLGP peptide-containing substrate. Cellular target engagement experiments further confirm the Naa50 binding of 4a and demonstrate its selectivity toward related enzymes (Naa10 and Naa60). Additional analogs of inhibitor 4a were also evaluated to study the binding mode observed in the cocrystal structures.

  DOI：

  10.1021/acsmedchemlett.0c00029
• 作为产物：
  描述：

  N-α-tert-butyloxycarbonyl-cis-4-hydroxy-D-proline ethyl ester 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 sodium azide 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 22.0~55.0 ℃ 、689.48 kPa 条件下， 反应 16.0h， 生成 (2R,4S)-1-BOC-4-氨基-吡咯烷-2-羧酸
  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。
• MELANOCORTIN RECEPTOR AGONISTS
  申请人：Choi Sung Pil

  公开号：US20090298829A1

  公开（公告）日：2009-12-03

  The present invention relates to a compound of the following formula 1, pharmaceutically acceptable salt and isomer thereof effective as agonist of melanocortin receptor, and an agonistic composition of melanocortin receptor comprising the same as active ingredient.

  本发明涉及以下式子1的化合物，其药学上可接受的盐和异构体作为黑色素皮质素受体激动剂，以及包含其作为活性成分的黑色素皮质素受体激动剂组合物。
• Discovery of Subnanomolar Arginine-Glycine-Aspartate-Based α_Vβ₃/α_Vβ₅ Integrin Binders Embedding 4-Aminoproline Residues
  作者：Franca Zanardi、Paola Burreddu、Gloria Rassu、Luciana Auzzas、Lucia Battistini、Claudio Curti、Andrea Sartori、Giuseppe Nicastro、Gloria Menchi、Nicoletta Cini、Anna Bottonocetti、Silvia Raspanti、Giovanni Casiraghi

  DOI：10.1021/jm701214z

  日期：2008.3.1

  The embodiment of 4-aminoproline residues (Amp) into the arginine-glycine-aspartate (RGD) sequence led to the discovery of a novel class of high-affinity alpha v beta(3)/alpha v beta(5) integrin binders [IC50h(alpha v beta(3)) 0.03-5.12 nM; IC50h(alpha v beta(5)) 0.88-154 nM]. A total of eight cyclopeptides of type cyclo-[-Arg-Gly-Asp-Amp-], 5-12, were assembled by a standard solid-phase peptide synthesis protocol that involved the C2-carboxyl and C4-amino functionalities of the proline scaffolds, leaving the N-alpha-nuclear site untouched. Functionalization of this vacant proline site with either alkyl or acyl substituents proved feasible, with significant benefit to the integrin binding capabilities of the ligands. Notably, six out of eight cyclopeptide inhibitors, 5-7 and 9-11, showed moderate yet significant selectivity toward the alpha v beta(3) receptor. The three-dimensional structure in water was determined by NMR techniques and molecular dynamics calculations. Docking studies to the X-ray crystal structure of the extracellular segment of integrin alpha v beta(3) complexed with reference compound 1 were also performed on selected analogues to highlight the structural features required for potent ligand binding affinity.
• US5120859A
  申请人：——

  公开号：US5120859A

  公开（公告）日：1992-06-09
• US8183243B2
  申请人：——

  公开号：US8183243B2

  公开（公告）日：2012-05-22