L-苏氨酸乙酯盐酸盐 | 39994-70-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 苏氨酸类衍生物
• 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: L-苏氨酸乙酯盐酸盐
• 英文名称: L-threonine ethyl ester hydrochloride
• 英文别名: L-Thr-OEt hydrochloride；H-Thr-OEt hydrochloride；(2S,3R)-Ethyl 2-amino-3-hydroxybutanoate hydrochloride；ethyl (2S,3R)-2-amino-3-hydroxybutanoate;hydrochloride
• CAS: 39994-70-2
• 化学式: C₆H₁₃NO₃*ClH
• 分子量: 183.635
• InChiKey: WHKKNTASOQMDMH-JBUOLDKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.32
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥

制备方法与用途

(2S,3R)-2-氨基-3-羟基丁酸乙酯盐酸盐是一种苏氨酸衍生物。

反应信息

• 作为反应物：
  描述：

  S-Acetyl-N-[(Phenylmethoxy)carbonyl]-L-cysteine 、 L-苏氨酸乙酯盐酸盐 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3R)-2-((R)-3-Acetylsulfanyl-2-benzyloxycarbonylamino-propionylamino)-3-hydroxy-butyric acid ethyl ester
  参考文献：
  名称：

  S-酰基半胱氨酸肽。水解的合成和动力学。

  摘要：

  DOI：

  10.1021/jo00942a016
• 作为产物：
  描述：

  乙醇 、 L-苏氨酸 在 氯化亚砜 作用下， 反应 17.0h， 以92%的产率得到L-苏氨酸乙酯盐酸盐
  参考文献：
  名称：

  Synthesis and characterization of tailorable biodegradable thermoresponsive methacryloylamide polymers based on l-serine and l-threonine alkyl esters

  摘要：

  A series of monomers based on the methyl, ethyl, and isopropyl esters of N-alpha-(methacryloyl)-serine and -threonine were synthesized, and used in an AIBN-initiated radical polymerization reaction to yield polymers with an M-n ranging between 6.6 and 23.8 kDa. The newly synthesized polymers showed LCST behavior in aqueous solution that could be tailored by subtle variations of the hydrophobicity of the monomers to obtain a broad range of cloud points between 1.5 and >100 degrees C. According to HPLC, the hydrolytic t(1/2)-values (pH 7.4 at 37 degrees C) of the monomers were found to be 5, 12, and 40 days of the methyl, ethyl, and isopropyl esters, respectively, while the hydrolysis rate of poly[M-alpha-(methacryloyl)-Ser-OMe] and poly[N-alpha-(methacryloyl)-Thr-Ome] was found to be significantly lower compared to the corresponding monomers. In order to obtain thermoresponsive nanoparticles, N-alpha-(methacryloyl)-Thr-OEt was polymerized with (PEG monomethyl ether 5000)(2)-ABCPA as macroinitiator to yield an amphiphilic block co-polymer, poly[N-alpha-(methacryloyl)-Thr-OEt]-b-(PEG monomethyl ether 5000), which forms particles of 300 nm at a temperature higher than its cloud point of 24 degrees C. Incubation at physiological conditions induced ester hydrolysis resulting in a destabilization of the particles making these particles suitable for drug delivery purposes. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2010.04.010

文献信息

• Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes with Carbanions of Protected Serine and Threonine Esters
  作者：Daniel Sulikowski、Mieczysław Mąkosza

  DOI：10.1002/ejoc.201000498

  日期：2010.8

  serine and threonine esters with nitroarenes were studied. The main process involves the addition of the carbanions to the para position of the nitroarenes, which is occupied by a hydrogen atom, to form σ H adducts that are subsequently oxidized by 2,3-dichloro-5,6-dicyanobenzoquinone to give p-nitroaryl derivatives of the protected serine and threonine. Oxidation of the σ H adducts with dimethyldioxirane

  研究了受保护的丝氨酸和苏氨酸酯的碳负离子与硝基芳烃的反应。主要过程包括将碳负离子添加到被氢原子占据的硝基芳烃的对位，形成 σ H 加合物，随后被 2,3-二氯-5,6-二氰基苯醌氧化生成对-受保护的丝氨酸和苏氨酸的硝基芳基衍生物。σ H 加合物与二甲基二环氧乙烷的氧化导致这些氨基酸相应对羟基芳基衍生物的形成。受保护的苏氨酸酯的碳负离子的加成是一个高度立体选择性的过程，由苏氨酸的第二手性中心控制。
• Chemical Synthesis of a Heat-stable Enterotoxin Produced by Enterotoxigenic<i>Escherichia coli</i>Strain 18D
  作者：Shoko Yoshimura、Makoto Miki、Haruo Ikemura、Saburo Aimoto、Yasutsugu Shimonishi、Tae Takeda、Yoshifumi Takeda、Toshio Miwatani

  DOI：10.1246/bcsj.57.125

  日期：1984.1

  Two peptides with the two primary structures of 18 amino acid residues proposed for a heat-stable enterotoxin from enterotoxigenic Escherichia coli strain 18D were synthesized by solution methods and their physicochemical and biological properties were compared with those of native toxin. One of these peptides (Asn–Thr–Phe–Tyr–Cys–Cys–Glu–Leu–Cys–Cys–Asn–Pro–Ala–Cys–Ala–Gly–Cys–Tyr) showed the same heat-stability and 1H-NMR spectrum as those of the native toxin and evoked fluid secretion in suckling mice at a dose of 1.5–2.0 ng, which is similar to the effective dose of native toxin. Moreover, its toxicity was neutralized by antisera against the native toxin. The other peptide (Asn–Thr–Phe–Tyr–Cys–Cys–Glu–Leu–Cys–Cys–Tyr–Pro–Ala–Cys–Ala–Gly–Cys–Asn) showed different physicochemical and biological behaviors from those of the native toxin and exhibited toxic activity at a dose of 50–80 ng, which is about thirty times the effective dose of the native toxin. Moreover, its toxicity was not neutralized by antisera against the native toxin. These observations indicate that the former peptide is identical to native toxin but that the latter peptide differs in properties from the native toxin.

  利用溶液法合成了产肠毒素大肠杆菌18D菌株中一种热稳定肠毒素所提出的两种由18个氨基酸残基组成的主要结构肽段，并将其理化性质和生物学性质与天然毒素进行了比较。其中一种肽段（天冬酰胺-苏氨酸-苯丙氨酸-酪氨酸-半胱氨酸-半胱氨酸-谷氨酸-亮氨酸-半胱氨酸-半胱氨酸-天冬酰胺-脯氨酸-丙氨酸-半胱氨酸-丙氨酸-甘氨酸-半胱氨酸-酪氨酸）与天然毒素表现出相同的热稳定性、1H-NMR 谱图，且在 1.5-2.0 ng 剂量下诱发乳鼠分泌液体，这与天然毒素的有效剂量相似。此外，该肽段的毒性可被针对天然毒素的抗血清中和。另一种肽段（天冬酰胺-苏氨酸-苯丙氨酸-酪氨酸-半胱氨酸-半胱氨酸-谷氨酸-亮氨酸-半胱氨酸-半胱氨酸-酪氨酸-脯氨酸-丙氨酸-半胱氨酸-丙氨酸-甘氨酸-半胱氨酸-天冬酰胺）与天然毒素表现出不同的理化性质和生物学行为，其毒性活动所需的剂量为50-80ng，约为天然毒素有效剂量的三十倍。此外，该肽段的毒性不能被针对天然毒素的抗血清中和。这些观察结果表明，前一种肽段与天然毒素相同，但后一种肽段在性质上与天然毒素不同。
• Controlled Ring Opening of <i>N</i>-Sulfinyl- and <i>N</i>-Silyl-<i>N</i>-carboxyanhydrides (NCA): One-Pot Synthesis of Dipeptides and Unsymmetrical Peptidyl Ureas from Unprotected NCA
  作者：Vincent Levacher、Julia Mateos-Caro、Yves Robin、Francis Marsais

  DOI：10.1055/s-0028-1087510

  日期：——

  We report herein new labile protecting groups of N-carboxyanhydrides (NCA) useful to prevent polymerization during coupling reactions with nitrogen nucleophiles. Thus, N-sulfinyl-NCA 1 and N-silyl-NCA 2 were prepared in situ and involved, without being isolated, in coupling reactions with various α-amino esters to furnish dipeptides 3 and unsymmetrical peptidyl ureas 4, respectively, in good yields.

  我们在此报道了新的N-羧基环内酐（NCA）不稳定保护基团，这些基团在氮亲核试剂参与的偶联反应中能有效防止聚合反应的发生。因此，N-亚砜基NCA 1和N-硅基NCA 2在反应中现场制备，并未分离出来，而是直接与各种α-氨基酯进行偶联反应，分别以良好收率得到了二肽3和不对称肽脲4。
• Notiz zur Oxydation von <i>N</i> ‐Acyl‐serin‐ und ‐threonin‐Derivaten mit Blei(IV)‐acetat
  作者：Walter Oettmeier

  DOI：10.1002/cber.19701030738

  日期：1970.7

  No abstract is available for this article.

  本文没有摘要。
• [EN] PYRAZOLOPYRIMIDINE COMPOUNDS AND THEIR USE AS PDE10 INHIBITORS<br/>[FR] COMPOSÉS PYRAZOLOPYRIMIDINES ET LEUR UTILISATION COMME INHIBITEUR DE LA PDE10
  申请人：MITSUBISHI TANABE PHARMA CORP

  公开号：WO2011105628A1

  公开（公告）日：2011-09-01

  The present invention relates to a compound represented by formula [I]: wherein: R1 is hydrogen, halogen, lower alkyl or cyano; Ring A is an optionally substituted heterocyclic group; Ring B is an optionally substituted 3 to 6-membered monocyclic group; and Y is optionally substituted amino, optionally substituted cyclic amino, optionally substituted aliphatic 3 to 6-membered monocyclyloxy, optionally substituted lower alkyl or optionally substituted lower alkyl-O-, or a pharmaceutically acceptable salt thereof, and to their use as PDE10 inhibitor.

  本发明涉及一种由式[I]表示的化合物，其中：R1是氢、卤素、较低的烷基或氰基；环A是可选择取代的杂环基团；环B是可选择取代的3至6元杂环基团；Y是可选择取代的氨基、可选择取代的环氨基、可选择取代的脂肪族3至6元单环氧基、可选择取代的较低的烷基或可选择取代的较低的烷基-O-，或其药学上可接受的盐，以及它们作为PDE10抑制剂的用途。