H-L-Arg(Cbz)₂-OH

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: H-L-Arg(Cbz)₂-OH
• 英文别名: (2S)-2-amino-5-[bis(phenylmethoxycarbonylamino)methylideneamino]pentanoic acid
• 化学式: C₂₂H₂₆N₄O₆
• mdl: MFCD00083284
• 分子量: 442.472
• InChiKey: YVEVTHZNIALJHD-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  H-L-Arg(Cbz)₂-OH 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 2,2,2-三氟乙醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 33.0h， 生成 阿加曲班
  参考文献：
  名称：

  哌啶酰胺的高效非对映选择性三组分合成

  摘要：

  报道了一种用于合成哌啶酰胺的高效 Ugi 型三组分反应 (U-3CR)。电子不同的异氰化物、羧酸和 4-取代的 Δ1-哌啶之间的 U-3CR 以高度非对映选择性的方式进行。Δ1-哌啶是通过相应的 4-取代哌啶的 NCS 介导氧化获得的，而 4-取代哌啶又是通过有效的两步程序产生的，包括 4-甲基吡啶的烷基化和随后的吡啶环催化氢化。我们证明了这种 U-3CR 与可转化异氰化物 2-bromo-6-isocyanopyridine 在合成抗凝剂阿加曲班中的效用。

  DOI：

  10.1002/ejoc.201900399
• 作为产物：
  描述：

  Boc-Arg(Cbz)₂-OH 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 H-L-Arg(Cbz)₂-OH
  参考文献：
  名称：

  哌啶酰胺的高效非对映选择性三组分合成

  摘要：

  报道了一种用于合成哌啶酰胺的高效 Ugi 型三组分反应 (U-3CR)。电子不同的异氰化物、羧酸和 4-取代的 Δ1-哌啶之间的 U-3CR 以高度非对映选择性的方式进行。Δ1-哌啶是通过相应的 4-取代哌啶的 NCS 介导氧化获得的，而 4-取代哌啶又是通过有效的两步程序产生的，包括 4-甲基吡啶的烷基化和随后的吡啶环催化氢化。我们证明了这种 U-3CR 与可转化异氰化物 2-bromo-6-isocyanopyridine 在合成抗凝剂阿加曲班中的效用。

  DOI：

  10.1002/ejoc.201900399

文献信息

• Preparation of Boc-Amino-Acid or Peptide Aldehydesvia Reduction of Corresponding Phenyl Esters
  作者：Pavol Zlatoidsky

  DOI：10.1002/hlca.19940770117

  日期：1994.2.9

  A new alternative method for the preparation of amino-acid and peptide aldehydes based on reduction of corresponding phenyl esters with lithium tri(tert-butoxy)aluminium hydride is described.

  描述了一种新的替代方法，用于制备氨基酸和肽醛，其基于将相应的苯基酯用三（叔丁氧基）氢化铝锂还原。
• Peptide Bond Formation of Amino Acids by Transient Masking with Silylating Reagents
  作者：Wataru Muramatsu、Hisashi Yamamoto

  DOI：10.1021/jacs.1c02600

  日期：2021.5.12

  A one-pot peptide bond-forming reaction has been developed using unprotected amino acids and peptides. Two different silylating reagents, HSi[OCH(CF3)2]3 and MTBSTFA, are instrumental for the successful implementation of this approach, being used for the activation and transient masking of unprotected amino acids and peptides at C-termini and N-termini, respectively. Furthermore, CsF and imidazole

  使用未受保护的氨基酸和肽开发了一种一锅式肽键形成反应。两种不同的甲硅烷基化试剂 HSi[OCH(CF 3 ) 2 ] 3和 MTBSTFA 有助于成功实施该方法，用于激活和瞬时掩蔽C端和N端未受保护的氨基酸和肽， 分别。此外，CsF 和咪唑用作催化剂，活化 HSi[OCH(CF 3 ) 2 ] 3并且还加速化学选择性硅烷化。这种方法是通用的，因为它可以容忍带有一系列官能团的侧链，同时提供高达 99% 以上的相应肽收率，而无需任何外消旋或聚合。
• Isolement à partir de l'hypophyse postérieure du tripeptide leucyl-arginyl-leucine et sa synthèse par une route nouvelle quant à l'incorporation de l'arginine
  作者：Claude Gros、Michel Privat de Garilhe、Antigone Costopanagiotis、Robert Schwyzer

  DOI：10.1002/hlca.19610440730

  日期：——

  A basic peptide isolated from hog posterior pituitary was shown to have the structure leucyl-arginyl-leucine. A tripeptide of the same sequence was synthesized; both the natural and the synthetic tripeptide behave identically in chromatography and electrophoresis on paper. The physiological meaning of the compound is still unknown.

  从猪垂体后叶分离的碱性肽显示具有亮氨酰-精氨酰-亮氨酸的结构。合成了相同序列的三肽；天然和合成三肽在色谱和纸上电泳时的行为相同。该化合物的生理意义仍然未知。
• Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,
  作者：Dao Feng Xiang、Yury Patskovsky、Chengfu Xu、Alexander A. Fedorov、Elena V. Fedorov、Abby A. Sisco、J. Michael Sauder、Stephen K. Burley、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi100897u

  日期：2010.8.10

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).
• Total Synthesis of Pyoverdin D
  作者：Roi Mashiach、Michael M. Meijler

  DOI：10.1021/ol400490s

  日期：2013.4.5

  Pyoverdin D is an Important siderophore that is used by the human pathogen Pseudomonas aeruginosa to import iron and gain a competitive advantage. This unique partially cyclic octapeptide bears four nonproteinogenic amino acids, including N-delta-formyl-N-delta-hydroxy-L-ornithine, and a catechol containing chiral chromophore. Here, we report the first total synthesis of pyoverdin D.