(S)-4-hydroxy-1-methoxy-1-oxobutan-2-aminium chloride

• 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
• 英文名称: (S)-4-hydroxy-1-methoxy-1-oxobutan-2-aminium chloride
• 英文别名: L-homoserine methyl ester hydrochloride；(S)-Methyl 2-amino-4-hydroxybutanoate hydrochloride；methyl (2S)-2-amino-4-hydroxybutanoate;hydrochloride
• 化学式: C₅H₁₁NO₃*ClH
• 分子量: 169.608
• InChiKey: UFMGWJYGVSOBAG-WCCKRBBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.71
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-hydroxy-1-methoxy-1-oxobutan-2-aminium chloride 在 咪唑 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 9.0h， 生成 methyl N-(4-bromobut-3-yn-1-yl)-O-(tert-butyldimethylsilyl)-N-((2,4-dinitrophenyl)sulfonyl)-L-homoserinate
  参考文献：
  名称：

  通过手性记忆实现杂环取代炔烃的碳环化：获得Cα取代的脯氨酸衍生物。

  摘要：

  已经建立了从无环α-氨基酸不对称合成Cα-取代的脯氨酸衍生物的有效策略。通过手性概念的记忆，α-氨基酯烯酸酯的5-exo-dig不对称环化成杂取代的炔烃提供了具有优异对映选择性的产物。密度泛函理论计算表明，杂原子对于不对称环化的成功至关重要，因为会产生更稳定的乙烯基碳负离子。这种新方法具有使包含吡咯烷骨架的生物活性分子快速不对称构建的潜力。

  DOI：

  10.1021/acs.joc.9b01800
• 作为产物：
  描述：

  甲醇 、 L-高丝氨酸 在 氯化亚砜 作用下， 反应 12.5h， 以100%的产率得到(S)-4-hydroxy-1-methoxy-1-oxobutan-2-aminium chloride
  参考文献：
  名称：

  Solution structural features of N -acyl homoserine lactones

  摘要：

  Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e(-) withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (<0.05 kcal mol(-1)) contacts between N-acyl O and lactone C'. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.08.078

文献信息

• [EN] INHIBITORS OF PEPTIDYL ARGININE DEIMINASE (PAD) ENZYMES AND USES THEREOF<br/>[FR] INHIBITEURS D'ENZYMES PEPTIDYL ARGININE DÉSIMINASES (PAD) ET LEURS UTILISATIONS
  申请人：UNIV HEALTH NETWORK

  公开号：WO2017027967A1

  公开（公告）日：2017-02-23

  The present application relates to a-substituted amino acid compounds of the Formula (I), compositions comprising these compounds and their use, in particular for the treatment of diseases, disorders or conditions characterized by or associated with the hypercitrullination of proteins by peptidyl arginine deiminase (PAD) enzymes.

  本申请涉及公式（I）的a-取代氨基酸化合物，包含这些化合物的组合物以及它们的用途，特别是用于治疗由肽精氨酸脱亚硝酰酶（PAD）酶引起的蛋白质高环氨酸化特征或相关的疾病、紊乱或状况。
• <i>N</i>-Arylalkyl Pseudopeptide Inhibitors of Farnesyltransferase
  作者：S. Jane deSolms、Elizabeth A. Giuliani、Samuel L. Graham、Kenneth S. Koblan、Nancy E. Kohl、Scott D. Mosser、Allen I. Oliff、David L. Pompliano、Elaine Rands、Thomas H. Scholz、Catherine M. Wiscount、Jackson B. Gibbs、Robert L. Smith

  DOI：10.1021/jm9800907

  日期：1998.7.1

  Inhibitors of Ras protein farnesyltransferase are described which are reduced pseudopeptides related to the C-terminal tetrapeptide of the Ras protein that signals farnesylation. Reduction of the carbonyl groups linking the first three residues of the tetrapeptide leads to active inhibitors which are chemically unstable. Stability can he restored by alkylating the central amine of the tetrapeptide. Studies of the SAR of these alkylated pseudopeptides with concomitant modification of the side chain of the third residue led to 2(S)-(2(S)-[2(S)-(2(R)-amino-3-mercaptopropylamino)-3-(S)-methylpentyl]naphthalen-1-ylmethylamino}acetylamino)-4-methylsulfanylbutyric acid (11), a subnanomolar inhibitor. The methyl ester (10) of this compound exhibited submicromolar activity in the processing assay and selectively inhibited anchorage-independent growth of Rat1 cells transformed by v-ras at 2.5-5 mu M.
• US4273704A
  申请人：——

  公开号：US4273704A

  公开（公告）日：1981-06-16
• Carbocyclization of Heterosubstituted Alkynes via the Memory of Chirality: Access to Cα-Substituted Proline Derivatives
  作者：Shenpeng Tan、Feng Li、Soojun Park、Sanghee Kim

  DOI：10.1021/acs.joc.9b01800

  日期：2019.11.15

  An efficient strategy for the asymmetric synthesis of Cα-substituted proline derivatives from acyclic α-amino acids has been established. The 5-exo-dig asymmetric cyclization of α-amino ester enolates onto heterosubstituted alkynes provided a product with excellent enantioselectivity via the memory of chirality concept. Density functional theory calculations indicated that a heteroatom is crucial for

  已经建立了从无环α-氨基酸不对称合成Cα-取代的脯氨酸衍生物的有效策略。通过手性概念的记忆，α-氨基酯烯酸酯的5-exo-dig不对称环化成杂取代的炔烃提供了具有优异对映选择性的产物。密度泛函理论计算表明，杂原子对于不对称环化的成功至关重要，因为会产生更稳定的乙烯基碳负离子。这种新方法具有使包含吡咯烷骨架的生物活性分子快速不对称构建的潜力。
• Solution structural features of N -acyl homoserine lactones
  作者：Shama Tumminakatti、Bhavesh Khatri、Vinayak Krishnamurti、Vishikh Athavale、Erode N. Prabhakaran

  DOI：10.1016/j.tetlet.2015.08.078

  日期：2015.10

  Here we demonstrate that in interbacterial quorum signal moderators, N-acylhomoserine lactones (AHLs), the stabilization of bioactive pharmacophore lactone against lysis is through the e(-) withdrawing N-acyl motif which reduces lactone carbonyl polarization. This lysis is assisted by weak (<0.05 kcal mol(-1)) contacts between N-acyl O and lactone C'. The interactions that preclude this weak contact, in the free and receptor-bound AHLs, improve lactone halflife and hence are key to the design of the antibacterial AHL analogues. (C) 2015 Elsevier Ltd. All rights reserved.