benzyl (S)-2-((tert-butoxycarbonyl)amino)but-3-enoate | 104523-58-2

• 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: benzyl (S)-2-((tert-butoxycarbonyl)amino)but-3-enoate
• 英文别名: Boc-L-vinylglycine-OBn；benzyl (S)-2-tert-butyloxycarbonylamino-but-3-enoate；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]but-3-enoate
• CAS: 104523-58-2
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: STOSCTZEMODUNK-ZDUSSCGKSA-N

物化性质

• 沸点：
  414.3±40.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (S)-2-((tert-butoxycarbonyl)amino)but-3-enoate 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以70%的产率得到(S)-乙烯基甘氨酸盐酸盐
  参考文献：
  名称：

  2-硒代吡啶-N-氧化物羧酸酯的自由基化学：（L）-乙烯基甘氨酸的简便合成

  摘要：

  光学纯的（L）-乙烯基甘氨酸已经通过两种不同的方法合成。这些中的第一个涉及N-羟基-2-硒代吡啶的受保护的（L）-谷氨酸酯。这类酯显示出与其硫代类似物相同的脱羧基重排。用臭氧氧化除去硒吡啶吡啶残基，并借助于己烯-1-烯作为后处理的牺牲烯烃，得到所需的（L）-乙烯基甘氨酸衍生物。类似地，在适当保护的（L）-谷氨酸衍生物的末端羧基上的修饰的Hunsdiecker反应产生了正溴化物，其在用苯基硒化物阴离子处理时容易得到相应的苯基硒化物。顺序则如上所述。

  DOI：

  10.1016/s0040-4020(01)97206-0
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 sodium periodate 、 三甲氧基磷 作用下， 以 xylene 为溶剂， 反应 24.0h， 生成 benzyl (S)-2-((tert-butoxycarbonyl)amino)but-3-enoate
  参考文献：
  名称：

  Synthesis of 2'-epi-distichonic acid A, an iron-chelating amino acid derivative.

  摘要：

  从L-乙烯基甘氨酸环氧化物（6b）出发，合成了一种铁螯合氨基酸衍生物2'-表双歧酸A（4b）。6b与甘氨酸酯17反应得到β-羟基氨基酸衍生物（18）。由18衍生的21与L-苹果酸-β-半醛（25）进行还原偶联，去保护后得到2'-表双歧酸A（4b）。

  DOI：

  10.1248/cpb.36.893

文献信息

• [EN] CYCLIC PEPTIDE ANTIBIOTICS<br/>[FR] ANTIBIOTIQUES PEPTIDIQUES CYCLIQUES
  申请人：GENENTECH INC

  公开号：WO2020185999A1

  公开（公告）日：2020-09-17

  Provided herein are antibacterial compounds, wherein the compounds in some embodiments have broad spectrum bioactivity. In various embodiments, the compounds act by inhibition of lipoprotein signal peptidase II (LspA), a key protein in bacteria. Pharmaceutical compositions and methods for treatment using the compounds described herein are also provided.

  本发明提供了抗菌化合物，其中在某些实施例中，这些化合物具有广谱生物活性。在各种实施例中，这些化合物通过抑制细菌中的关键蛋白质——脂蛋白信号肽酶II（LspA）发挥作用。还提供了使用本发明所述化合物的药物组合物和治疗方法。
• Short, stereoselective synthesis of C-glycosyl asparagines via an olefin cross-metathesis
  作者：Ernest G Nolen、Adam J Kurish、Kelli A Wong、Michael D Orlando

  DOI：10.1016/s0040-4039(03)00350-2

  日期：2003.3

  The Grubbs second generation ruthenium catalyst was employed for the cross metathesis between α- and β-C-allyl glycosides and suitably protected l-vinyl glycines to furnish olefinic products in 57–94% yields. Hydrogenation afforded the C-glycosyl asparagines in high yield.

  Grubbs第二代钌催化剂用于α-和β- C-烯丙基糖苷与适当保护的1-乙烯基甘氨酸之间的交叉复分解，以57-94％的收率提供烯烃产品。氢化以高收率提供了C-糖基天冬酰胺。
• 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.
• Reconstitution of Peptidoglycan Cross-Linking Leads to Improved Fluorescent Probes of Cell Wall Synthesis
  作者：Matthew D. Lebar、Janine M. May、Alexander J. Meeske、Sara A. Leiman、Tania J. Lupoli、Hirokazu Tsukamoto、Richard Losick、David Z. Rudner、Suzanne Walker、Daniel Kahne

  DOI：10.1021/ja505668f

  日期：2014.8.6

  The peptidoglycan precursor, Lipid II, produced in the model Gram-positive bacterium Bacillus subtilis differs from Lipid II found in Gram-negative bacteria such as Escherichia coli by a single amidation on the peptide side chain. How this difference affects the cross-linking activity of penicillin-binding proteins (PBPs) that assemble peptidoglycan in cells has not been investigated because B. subtilis Lipid II was not previously available. Here we report the synthesis of B. subtilis Lipid II and its use by purified B. subtilis PBP1 and E. coli PBP1A. While enzymes from both organisms assembled B. subtilis Lipid II into glycan strands, only the B. subtilis enzyme cross-linked the strands. Furthermore, B. subtilis PBP1 catalyzed the exchange of both D-amino acids and D-amino carboxamides into nascent peptidoglycan, but the E. coli enzyme only exchanged n-amino acids. We exploited these observations to design a fluorescent n-amino carboxamide probe to label B. subtilis PG in vivo and found that this probe labels the cell wall dramatically better than existing reagents.
• Stereoselective Synthesis of α-<i>C</i>-Glucosyl Serine and Alanine via a Cross-Metathesis/Cyclization Strategy
  作者：Ernest G. Nolen、Adam J. Kurish、Jennifer M. Potter、Lawrence A. Donahue、Michael D. Orlando

  DOI：10.1021/ol051341q

  日期：2005.7.1

  C-Glycosyl amino acids represent stable mimics of monomeric units within natural O-linked glycoproteins. Olefin cross-metathesis has been used to provide alkene precursors for a mercury(II)-mediated cyclization, yielding alpha-C-glucosyl serine and alanine.