5-[benzyloxy(methyl)amino]-5-oxopentanoic acid | 117686-97-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-[benzyloxy(methyl)amino]-5-oxopentanoic acid
• 英文别名: 5-[Methyl(phenylmethoxy)amino]-5-oxopentanoic acid
• CAS: 117686-97-2
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: ZVMPEIVRPVPCIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[benzyloxy(methyl)amino]-5-oxopentanoic acid 在 吡啶 、 4-二甲氨基吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 N1,N4,N8-Tris(N-methyl-N-(benzyloxy)glutaramoyl)spermidine
  参考文献：
  名称：

  Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs

  摘要：

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.

  DOI：

  10.1021/jm00122a013
• 作为产物：
  描述：

  O-苄基羟胺 在 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.33h， 生成 5-[benzyloxy(methyl)amino]-5-oxopentanoic acid
  参考文献：
  名称：

  COMPOUND FOR PREPARATION OF ANTIBODY-PAYLOAD CONJUGATE AND USE THEREOF

  摘要：

  本申请涉及一种用于生物共轭的新型连接剂，包括一个或多个羰基中的两个或更多亲电性碳原子和一个click化学的功能基团，更具体地说，涉及一种连接剂，通过该连接剂，化合物、肽和/或蛋白质可以通过取代反应直接和/或间接地连接到所需的目标分子，即目标分子。

  公开号：

  US20220072147A1

文献信息

• Isoprenoid Biosynthesis via the Methylerythritol Phosphate Pathway: Structural Variations around Phosphonate Anchor and Spacer of Fosmidomycin, a Potent Inhibitor of Deoxyxylulose Phosphate Reductoisomerase
  作者：Catherine Zinglé、Lionel Kuntz、Denis Tritsch、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1021/jo9024732

  日期：2010.5.21

  Fosmidomycin and its analogue FR-900098 are potent inhibitors of 1-deoxy-d-xylulose 5-phosphate reducto-isomerase (DXR), the second enzyme of the MEP pathway for the biosynthesis of isoprenoids. This paper describes the synthesis of analogues of the two reverse phosphonohydroxamic acids 3 and 4, in which the length of the carbon spacer is modified, the N-methyl group of 3 is replaced by an ethyl group

  膦胺霉素和其类似物FR-900098是1-脱氧的有效抑制剂d -xylulose -5-磷酸粉身碎骨异构酶（DXR），为类异戊二烯的生物合成的MEP途径的第二种酶。本文描述的两个倒phosphonohydroxamic酸类似物的合成3和4，其中，所述碳间隔的长度被修改，Ñ甲基组3是由乙基取代，和磷酸基团通过取代的潜在等位部分，即磺酸盐或羧酸盐官能团。评价了合成的类似物抑制大肠杆菌DXR的潜力。
• Synthesis and ESR study of new dihydroxamic acid siderophores S as scavengers of hydroxyl radicals
  作者：M.V.D. Nguyen、L. Nicolas、A. Gaudemer、M.E. Brik

  DOI：10.1016/s0960-894x(97)10219-0

  日期：1998.2

  Five new dihydroxamic acid ligands (L) (8, 10a, 10b, 10c and 13) have been synthesised and characterised as potential chelating agents for iron (Fe3+). The log stability constants of Fe2L3 and FeL+ from Fe3+ and L2- have been estimated to be log beta = 61.96 and log beta 1 = 22.8 respectively. The ability of these compounds to scavenge hydroxyl radicals (oOH) responsible for cell damage have been studied

  已经合成了五个新的二氢氧肟酸配体（L）（8、10a，10b，10c和13），并将其表征为铁（Fe3 +）的潜在螯合剂。来自Fe3 +和L2-的Fe2L3和FeL +的对数稳定常数估计分别为log beta = 61.96和log beta 1 = 22.8。这些化合物清除负责细胞损伤的羟基自由基（oOH）的能力已通过esr光谱研究。
• COMPOUND FOR PREPARATION OF ANTIBODY-PAYLOAD CONJUGATE AND USE THEREOF
  申请人：AbTis Co., Ltd.

  公开号：US20220072147A1

  公开（公告）日：2022-03-10

  The present application relates to a novel linker for use in bioconjugation, comprising two or more electrophilic carbon atoms of a carbonyl group, and a click chemistry functional group and, more specifically, to a linker through which a compound, a peptide, and/or a protein can be directly and/or indirectly linked by a substitution reaction to a desired target molecule, that is, a target molecule.

  本申请涉及一种用于生物共轭的新型连接剂，包括一个或多个羰基中的两个或更多亲电性碳原子和一个click化学的功能基团，更具体地说，涉及一种连接剂，通过该连接剂，化合物、肽和/或蛋白质可以通过取代反应直接和/或间接地连接到所需的目标分子，即目标分子。
• A Semi Rigid Novel Hydroxamate AMPED-Based Ligand for 89Zr PET Imaging
  作者：Lisa Russelli、Francesco De Rose、Loredana Leone、Sybille Reder、Markus Schwaiger、Calogero D’Alessandria、Lorenzo Tei

  DOI：10.3390/molecules26195819

  日期：——

  In this work, we designed, developed, characterized, and investigated a new chelator and its bifunctional derivative for 89Zr labeling and PET-imaging. In a preliminary study, we synthesized two hexadentate chelators named AAZTHAS and AAZTHAG, based on the seven-membered heterocycle AMPED (6-amino-6-methylperhydro-1,4-diazepine) with the aim to increase the rigidity of the 89Zr complex by using N-

  在这项工作中，我们设计、开发、表征和研究了一种用于89 Zr 标记和 PET 成像的新型螯合剂及其双功能衍生物。在初步研究中，我们基于七元杂环 AMPED（6-amino-6-methylperhydro-1,4-diazepine）合成了两种名为 AAZTHAS 和 AAZTHAG 的六齿螯合剂，目的是增加89 Zr 配合物的刚性通过使用连接到环状结构的N-甲基-N-（羟基）琥珀酰胺或N-甲基-N-（羟基）戊二酰胺悬垂臂。N-甲基异羟肟酸酯基团是选择的供体基团以有效协调89锆 在体外稳定性测试后，我们选择了臂更长的螯合剂 AAZTHAG 作为89 Zr的最佳络合剂，在人血清 (HS) 中至少 72 小时的稳定性为 86.4 ± 5.5%。然后在不同时间点（最多 24 小时）获得的小动物 PET/CT 静态扫描和离体器官分布研究在健康裸鼠（n = 3）中进行，以研究这种新的89 Zr的稳定
• Spermexatin and spermexatol: new synthetic spermidine-based siderophore analogs
  作者：Sushil K. Sharma、Marvin J. Miller、Shelley M. Payne

  DOI：10.1021/jm00122a013

  日期：1989.2

  Syntheses of hexanediamine-based dihydroxamate (Hexamate), spermidine-based trihydroxamate (Spermexatins), and spermidine-based mixed siderophore analogues (Spermexatols) are described. Key intermediates include the N-hydroxysuccinimide esters of various hydroxamic acids, e.g., malonohydroxamate, succinohydroxamate, and glutarohydroxamate. These intermediates were synthesized, characterized, and incorporated as the ligating chains on spermidine. Also, mixed iron chelating compounds (Spermexatols) with both catechol and hydroxamic acid side chains were synthesized. The reagent carbobenzoxyimidazole was employed to distinguish between the primary and secondary amino groups of spermidine. The ability of these iron chelators to stimulate microbial growth is also described.