benzyl (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate | 145967-50-6

• 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 (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate
• 英文别名: (S)-benzyl 3-azido-2-(tert-butoxycarbonylamino)propanoate；BocSer(Ms)OBn；(S)-benzyl 3-azido-2-(t-butoxycarbonylamino)propanoate；3-azido Boc-Ala-OBn；Boc-azidoalanine benzyl ester；benzyl (2S)-3-azido-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 145967-50-6
• 化学式: C₁₅H₂₀N₄O₄
• 分子量: 320.348
• InChiKey: GUSPIYFEJAYFEW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到2-氨基-3-叠氮基丙酸
  参考文献：
  名称：

  A Concise Route to l-Azidoamino Acids: l-Azidoalanine, l-Azidohomo­alanine and l-Azidonorvaline

  摘要：

  A simple and highly efficient synthetic route to three homologous azidoamino acids, starting from inexpensive, commercially available, protected natural amino acids is reported. The products can be used to introduce bioorthogonal handles into proteins.

  DOI：

  10.1055/s-0029-1218391
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三(2-氯乙基)胺 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 18.0h， 生成 benzyl (2S)-3-azido-2-[(tert-butoxycarbonyl)amino]propanoate
  参考文献：
  名称：

  设计用于呈现天冬氨酸侧链的手性3-氧代-6-[（苯基甲氧基）-羰基] -2-哌嗪乙酸酯的合成。随后的小说《弗里德尔工艺》的反应

  摘要：

  由L-或D-丝氨酸和二甲基合成（2 S，6 R）-和（2 S，6 S）-3-氧代-6-[（苯基甲氧基）羰基] -2，-哌嗪乙酸甲酯-描述了D-苹果酸。（2- S，6S）异构体用3-甲氧基苯基乙酰氯酰化，苄基酯氢解，然后用草酰氯处理，然后用氯化铝处理，得到意想不到的三环产物，其中引入了C 2 O 2单元。

  DOI：

  10.1016/s0040-4039(00)60843-2

文献信息

• Development of Stable Phosphohistidine Analogues
  作者：Jung-Min Kee、Bryeanna Villani、Laura R. Carpenter、Tom W. Muir

  DOI：10.1021/ja104393t

  日期：2010.10.20

  and Tyr residues, our understanding of histidine phosphorylation is relatively limited, particularly in higher eukaryotes, due to technical difficulties stemming from the intrinsic instability and isomerism of phosphohistidine (pHis). We report the design and synthesis of stable and nonisomerizable pHis analogues. These pHis analogues were successfully utilized in solid-phase peptide synthesis and semi-synthesis

  蛋白质磷酸化是最常见和最广泛研究的翻译后修饰 (PTM) 之一。与 Ser、Thr 和 Tyr 残基的 O 磷酸化相比，我们对组氨酸磷酸化的理解相对有限，尤其是在高等真核生物中，由于磷酸组氨酸 (pHis) 的内在不稳定性和异构现象所带来的技术困难。我们报告了稳定和非异构化 pHis 类似物的设计和合成。这些 pHis 类似物已成功用于固相肽合成和组蛋白 H4 的半合成。值得注意的是，使用合成肽作为免疫原获得了特异性识别pHis的第一抗体。
• The synthesis of chiral 3-oxo-6-[(phenylmethoxy)-carbonyl]-2-piperazineacetic acid esters designed for the presentation of an aspartic acid side chain. A subsequent novel Friedel Crafts reaction
  作者：Timothy P. Kogan、Thomas E. Rawson

  DOI：10.1016/s0040-4039(00)60843-2

  日期：1992.11

  The syntheses of (2S, 6R)-, and (2S, 6S)-3-oxo-6-[(phenylmethoxy)carbonyl]-2,-piperazineacetic acid methyl esters from L- or D-serine and dimethyl-D-malate are described. Acylation of the (2S, 6S) isomer with 3-methoxyphenylacetyl chloride, hydrogenolysis of the benzyl ester, followed by treatment with oxalyl chloride then aluminum chloride led to an unexpected tricyclic product into which a C2O2 unit

  由L-或D-丝氨酸和二甲基合成（2 S，6 R）-和（2 S，6 S）-3-氧代-6-[（苯基甲氧基）羰基] -2，-哌嗪乙酸甲酯-描述了D-苹果酸。（2- S，6S）异构体用3-甲氧基苯基乙酰氯酰化，苄基酯氢解，然后用草酰氯处理，然后用氯化铝处理，得到意想不到的三环产物，其中引入了C 2 O 2单元。
• Synthesis of crosslinking amino acids by click chemistry
  作者：Chun Li、Jie Tang、Juan Xie

  DOI：10.1016/j.tet.2009.07.054

  日期：2009.9

  Crosslinking amino acids are naturally existing protein crosslinkers. Herein, we described the synthesis of several novel bis-amino acids constituted of serine, alanine, lysine, and tyrosine with click chemistry. The Huisgen 1,3-dipolar cycloadditions between azido- and alkyne-functionalized amino acids can be easily realized in the presence of catalytic amount of CuSO4 and Na ascorbate. In addition

  交联氨基酸是天然存在的蛋白质交联剂。在这里，我们用点击化学描述了由丝氨酸，丙氨酸，赖氨酸和酪氨酸组成的几种新型双氨基酸的合成。在催化量的CuSO 4和抗坏血酸钠存在下，叠氮基和炔基官能化氨基酸之间的Huisgen 1,3-偶极环加成反应很容易实现。另外，还使用蒽，荧光素和苯并噻二唑作为荧光团制备了荧光双氨基酸衍生物。用对称的双炔苯并噻二唑，可以合成带有两个不同氨基酸部分的不对称衍生物。
• A Fluorogenic Probe for the Catalyst-Free Detection of Azide-Tagged Molecules
  作者：Frédéric Friscourt、Christoph J. Fahrni、Geert-Jan Boons

  DOI：10.1021/ja309000s

  日期：2012.11.14

  Fluorogenic reactions in which non- or weakly fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctine that under catalyst-free conditions undergoes fast strain promoted cycloadditions with azides to yield strongly fluorescent triazoles. The Cycloaddition products are more than 1000-fold brighter compared to the Starting cyclooctyne, exhibit large Stokes shift,. and can be excited above 350 nm, which is required for many applications. Quantum mechanical: calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S-0 <-> S-1 transitions in the planar C-2v-symmetric starting material compared to the symmetry broken and nonplanar.cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.
• Stable triazolylphosphonate analogues of phosphohistidine
  作者：Shin Mukai、Gavin R. Flematti、Lindsay T. Byrne、Paul G. Besant、Paul V. Attwood、Matthew J. Piggott

  DOI：10.1007/s00726-011-1145-2

  日期：2012.8

  Histidine-phosphorylated proteins and the corresponding kinases are important components of bacterial and eukaryotic cell-signalling pathways, and are therefore potential drug targets. The study of these biomolecules has been hampered by the lability of the phosphoramidate functional group in the phosphohistidines and the lack of generic antibodies. Herein, the design and concise synthesis of stable triazolylphosphonate analogues of N1- and N3-phosphohistidine, and derivatives suitable for bioconjugation, are described.