Boc-L-Met-L-Phe-OMe | 63473-46-1

• 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: Boc-L-Met-L-Phe-OMe
• 英文别名: Boc-Met-Phe-OMe；methyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoyl]amino]-3-phenylpropanoate
• CAS: 63473-46-1
• 化学式: C₂₀H₃₀N₂O₅S
• 分子量: 410.535
• InChiKey: ZXEDRKPVHZGNAD-HOTGVXAUSA-N

物化性质

• 熔点：
  55-60 °C
• 沸点：
  596.2±50.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-L-Met-L-Phe-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 L-methionyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  Methionine-enabled peptide modification through late-stage Pd-catalyzed β-C(sp3)–H olefination/cyclization

  摘要：

  We present a method for site-selective diversification of peptides via Pd-catalyzed β-C(sp3)–H olefination/cyclization.

  DOI：

  10.1039/d4cc02739f
• 作为产物：
  描述：

  Boc-L-Met-[(β-SH)-L-Phe]-OMe 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以70%的产率得到Boc-L-Met-L-Phe-OMe
  参考文献：
  名称：

  Native Chemical Ligation at Phenylalanine

  摘要：

  Synthesis of erythro-N-Boc-beta-mercapto-L-phenylalanine enables native chemical ligation at phenylalanine. In the form of the S-ethyldisulfanyl derivative, the N-Boc amino acid is used to cap a tetrapeptide generated by Fmoc-SPPS. The native chemical ligation with C-terminal thioesters then occurs successfully and is followed by selective desulfurization of the benzylic C-S bond. The method is applied to the synthesis of LYRAMFRANK, thereby establishing compatibility with the reactive side chains and the ability to ligate other than glycine.

  DOI：

  10.1021/ja072804l

文献信息

• Visible-Light-Driven, Copper-Catalyzed Decarboxylative C(sp³ )−H Alkylation of Glycine and Peptides
  作者：Chao Wang、Mengzhun Guo、Rupeng Qi、Qinyu Shang、Qiang Liu、Shan Wang、Long Zhao、Rui Wang、Zhaoqing Xu

  DOI：10.1002/anie.201809400

  日期：2018.11.26

  well‐developed and growing body of work in Cu catalysis, the potential of Cu to serve as a photocatalyst remains underexplored. Reported herein is the first example of visible‐light‐induced Cu‐catalyzed decarboxylative C(sp3)−H alkylation of glycine for preparing α‐alkylated unnatural α‐amino acids. It merits mentioning that the mild conditions and the good functional‐group tolerance allow the modification

  尽管铜催化方面的工作已经发展成熟并且在不断发展，但是铜作为光催化剂的潜力仍未得到开发。本文报道的是第一个可见光诱导的铜催化甘氨酸脱羧C（sp 3）-H烷基化制备甘氨酸α-烷基化非天然α-氨基酸的例子。值得一提的是，温和的条件和良好的官能团耐受性允许使用此方法对肽进行修饰。机理研究表明，该反应涉及自由基-自由基偶联途径。
• 9-Silafluorenyl Dichlorides as Chemically Ligating Coupling Agents and Their Application in Peptide Synthesis
  作者：Samuel J. Aspin、Sylvain Taillemaud、Patrick Cyr、André B. Charette

  DOI：10.1002/anie.201606120

  日期：2016.10.24

  A fundamentally simple, mild, and practical procedure for peptide bond formation is reported that employs a stoichiometric amount of easy‐to‐access 9‐silafluorenyl dichlorides as the coupling agent. Without initial preactivation or elaboration of the carboxylic acid or amine termini of the amino acids, the developed reagent is proposed to act through an unprecedented chemical ligation mechanism, bringing

  据报道，一种基本简单，温和且实用的肽键形成方法是采用化学计量的易于获得的9-二氟芴基二氯化物作为偶联剂。无需对氨基酸的羧酸或胺末端进行初步的预活化或精加工，就可以开发出一种通过空前的化学连接机制发挥作用的试剂，从而将两个偶联配偶体聚集在一起，然后再将其消除。因此以高收率和低至无差向异构化提供所需的酰胺或肽键。
• Pd-Catalyzed Site-Selective C(sp²)–H Olefination and Alkynylation of Phenylalanine Residues in Peptides
  作者：Yong Zheng、Weibin Song

  DOI：10.1021/acs.orglett.9b00987

  日期：2019.5.3

  Pd-catalyzed site-selective C(sp2)–H olefination and alkynylation of phenylalanine residues in peptides are described. The amino acids within the peptides are used as native bidentate directing groups to facilitate C–H functionalization. This protocol would provide appealing strategies for the postsynthetic modification of peptides.

  描述了钯催化的位点选择性C（sp 2）–H烯化和肽中苯丙氨酸残基的炔基化反应。肽中的氨基酸用作天然双齿引导基团，以促进C–H功能化。该协议将为多肽的后合成修饰提供有吸引力的策略。
• Small ring constrained peptidomimetics. Synthesis of aziridine parallel β-sheet mimetics
  作者：Silvia N. Filigheddu、Maurizio Taddei

  DOI：10.1016/s0040-4039(98)00632-7

  日期：1998.5

  a series of novel amino acids and peptides containing an aziridine ring is described. Their preparation is based on the Gabriel-Cromwell reaction of amino acids or peptides with different 2-bromo acrylates and acrylamides. These products are constituted by a turned scaffold (the aziridine) where two parallel peptidic strands can be grown to produce a β-sheet mimetic.

  描述了一系列含有氮丙啶环的新型氨基酸和肽的合成。它们的制备基于氨基酸或肽与不同的2-溴丙烯酸酯和丙烯酰胺的Gabriel-Cromwell反应。这些产物由翻转的支架（氮丙啶）构成，其中两条平行的肽链可以生长以产生β-折叠模拟物。
• Visible-Light-Induced Copper-Catalyzed Asymmetric C(sp³)–C(sp³)–H Glycosylation: Access to C-Glycopeptides
  作者：Ya-Nan Ding、Ning Li、Yan-Chong Huang、Yang An、Yong-Min Liang

  DOI：10.1021/acs.orglett.2c01501

  日期：2022.7.1

  a practical and highly efficient method for visible-light-induced copper-catalyzed N-aminoquinoline-directed asymmetric C(sp3)–C(sp3)–H glycosylation was reported. At the same time, C(sp3)–C(sp3)–H glycosylation of nondeoxysugars with amino acids to construct C-glycopeptides was achieved. This approach promoted the synthesis of various C-glycopeptides and provided a new model for the synthesis of

  本文报道了一种实用且高效的可见光诱导铜催化N-氨基喹啉定向不对称 C(sp 3 )-C(sp 3 )-H 糖基化方法。同时，实现了非脱氧糖与氨基酸的C(sp 3 )-C(sp 3 )-H糖基化构建C-糖肽。该方法促进了多种C-糖肽的合成，为C-糖氨基酸的合成提供了新的模型。