(S)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid | 1028258-40-3

• 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)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid
• 英文别名: (2S)-tert-butoxycarbonylamino-4-phenylselanyl-butyric acid；(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylselanylbutanoic acid
• CAS: 1028258-40-3
• 化学式: C₁₅H₂₁NO₄Se
• 分子量: 358.296
• InChiKey: JEENTLZSRCYYDG-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 palladium on carbon 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 31.75h， 生成 (2S,6R)-2-((tert-butoxycarbonyl)amino)-7-methoxy-7-oxo-6-(2,2,2-trifluoroacetamido)heptanoic acid
  参考文献：
  名称：

  Forming Cross-Linked Peptidoglycan from Synthetic Gram-Negative Lipid II

  摘要：

  The bacterial cell wall precursor, Lipid II, has a highly conserved structure among different organisms except for differences in the amino acid sequence of the peptide side chain. Here, we report an efficient and flexible synthesis of the canonical Lipid II precursor required for the assembly of Gram-negative peptidoglycan (PG). We use a rapid LC/MS assay to analyze PG glycosyltransfer (PGT) and transpeptidase (TP) activities of Escherichia coli penicillin binding proteins PBP1A and PBP1B and show that the native m-DAP residue in the peptide side chain of Lipid II is required in order for TP-catalyzed peptide cross-linking to occur in vitro. Comparison of PG produced from synthetic canonical E. coli Lipid II with PG isolated from E. coli cells demonstrates that we can produce PG in vitro that resembles native structure. This work provides the tools necessary for reconstituting cell wall synthesis, an essential cellular process and major antibiotic target, in a purified system.

  DOI：

  10.1021/ja312510m
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (S)-2-((tert-butoxycarbonyl)amino)-4-(phenylselanyl)butanoic acid
  参考文献：
  名称：

  A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone

  摘要：

  描述了从 L-高丝氨酸内酯合成 L-α-乙烯基甘氨酸的程序。所开发的路线方便（仅需要一个色谱步骤）且高效（71%；4 个步骤光学产率≥ 95%）。主要特点包括对氨基 (Bod) 和羧基（二苯基甲酯）基团使用酸不稳定保护基团，以及使用源自硼氢化钠和二苯基二硒化物的苯基硒酸盐等价物进行 L-高丝氨酸内酯裂解。

  DOI：

  10.1055/s-1996-4177

文献信息

• DEVELOPMENT OF A SYNTHESIS OF SYRINGOLIN A AND B AND DERIVATIVES THEREOF
  申请人：Kaiser Markus

  公开号：US20100022767A1

  公开（公告）日：2010-01-28

  The synthesis of syringolin A and B and derivatives thereof as well as to pharmaceutical compositions containing the syringolin A or B or derivatives thereof and the use of syringolin A and B and derivatives thereof for prophylaxis and treatment of cancer.

  合成Syringolin A和B及其衍生物，以及含有Syringolin A或B或其衍生物的药物组合物的用途，以及Syringolin A和B及其衍生物用于预防和治疗癌症。
• The natural product hybrid of Syringolin A and Glidobactin A synergizes proteasome inhibition potency with subsite selectivity
  作者：Jérôme Clerc、Nan Li、Daniel Krahn、Michael Groll、André S. Bachmann、Bogdan I. Florea、Herman S. Overkleeft、Markus Kaiser

  DOI：10.1039/c0cc02238a

  日期：——

  The preparation of a Syringolin A/Glidobactin A hybrid (SylA–GlbA) consisting of a SylA macrocycle connected to the GlbA side chain and its potent proteasome targeting of all three proteasomal subsites is reported. The influence of the syrbactin macrocycle moiety on subsite selectivity is demonstrated.

  报告制备了一种由连接到 GlbA 侧链的 SylA 大环组成的丁香菌素 A-Glidobactin A 混合物（SylA-GlbA），并对所有三个蛋白酶体亚位进行了有效的蛋白酶体靶向。研究证明了 SylA 大环对亚位点选择性的影响。
• Convergent Synthesis and Biological Evaluation of Syringolin A and Derivatives as Eukaryotic 20S Proteasome Inhibitors
  作者：Jérôme Clerc、Barbara Schellenberg、Michael Groll、André S. Bachmann、Robert Huber、Robert Dudler、Markus Kaiser

  DOI：10.1002/ejoc.201000317

  日期：2010.7

  A convergent synthesis of SylA was developed and consists of the synthesis of a fully functionalized macrocycle, which is subsequently coupled with a urea moiety. For cyclization, ring-closing metathesis of a conformationally preorganized precursor was employed. The established synthetic route was then applied to the synthesis of SylA derivatives by using various peptidic side chains for decoration

  开发了 SylA 的会聚合成，由全功能化大环的合成组成，随后与尿素部分偶联。对于环化，采用构象预组织前体的闭环复分解。然后通过使用各种肽侧链修饰SylA大环，将建立的合成路线应用于SylA衍生物的合成。对所得的 SylA 类似物集合进行了蛋白酶体抑制测试，表明聚乙二醇化 SylA 衍生物是最有效的蛋白酶体抑制剂。
• Forming Cross-Linked Peptidoglycan from Synthetic Gram-Negative Lipid II
  作者：Matthew D. Lebar、Tania J. Lupoli、Hirokazu Tsukamoto、Janine M. May、Suzanne Walker、Daniel Kahne

  DOI：10.1021/ja312510m

  日期：2013.3.27

  The bacterial cell wall precursor, Lipid II, has a highly conserved structure among different organisms except for differences in the amino acid sequence of the peptide side chain. Here, we report an efficient and flexible synthesis of the canonical Lipid II precursor required for the assembly of Gram-negative peptidoglycan (PG). We use a rapid LC/MS assay to analyze PG glycosyltransfer (PGT) and transpeptidase (TP) activities of Escherichia coli penicillin binding proteins PBP1A and PBP1B and show that the native m-DAP residue in the peptide side chain of Lipid II is required in order for TP-catalyzed peptide cross-linking to occur in vitro. Comparison of PG produced from synthetic canonical E. coli Lipid II with PG isolated from E. coli cells demonstrates that we can produce PG in vitro that resembles native structure. This work provides the tools necessary for reconstituting cell wall synthesis, an essential cellular process and major antibiotic target, in a purified system.
• A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone
  作者：David B. Berkowitz、Marianne K. Smith

  DOI：10.1055/s-1996-4177

  日期：1996.1

  A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (71%; ≥ 95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Bod) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.

  描述了从 L-高丝氨酸内酯合成 L-α-乙烯基甘氨酸的程序。所开发的路线方便（仅需要一个色谱步骤）且高效（71%；4 个步骤光学产率≥ 95%）。主要特点包括对氨基 (Bod) 和羧基（二苯基甲酯）基团使用酸不稳定保护基团，以及使用源自硼氢化钠和二苯基二硒化物的苯基硒酸盐等价物进行 L-高丝氨酸内酯裂解。