Boc-Phe-Ala-OEt | 78605-47-7

• 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-Phe-Ala-OEt
• 英文别名: N-BOC-L-Phe-L-Ala-OEt；ethyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]propanoate
• CAS: 78605-47-7
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: FZUYBVXALZHIGU-ZFWWWQNUSA-N

物化性质

• 熔点：
  94-97 °C
• 沸点：
  535.9±50.0 °C(Predicted)
• 密度：
  1.116±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Ala-OEt 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 ethyl N-benzoyl-L-phenylalanyl-L-alaninate
  参考文献：
  名称：

  The Discovery of Potent, Selective, and Reversible Inhibitors of the House Dust Mite Peptidase Allergen Der p 1: An Innovative Approach to the Treatment of Allergic Asthma

  摘要：

  Blocking the bioactivity of allergens is conceptually attractive as a small-molecule therapy for allergic diseases but has not been attempted previously. Group 1 allergens of house dust mites (HDM) are meaningful targets in this quest because they are globally prevalent and clinically important triggers of allergic asthma. Group 1 HDM allergens are cysteine peptidases whose proteolytic activity triggers essential steps in the allergy cascade. Using the HDM allergen Der p 1 as an archetype for structure-based drug discovery, we have identified a series of novel, reversible inhibitors. Potency and selectivity were manipulated by optimizing drug interactions with enzyme binding pockets, while variation of terminal groups conferred the physicochemical and pharmacokinetic attributes required for inhaled delivery. Studies in animals challenged with the gamut of HDM allergens showed an attenuation of allergic responses by targeting just a single component, namely, Der p 1. Our findings suggest that these inhibitors may be used as novel therapies for allergic asthma.

  DOI：

  10.1021/jm501102h
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanine 9-fluorenylmethyl thioester 在 哌啶 、 N,O-双三甲硅基乙酰胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 13.0h， 生成 Boc-Phe-Ala-OEt
  参考文献：
  名称：

  In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

  摘要：

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

  DOI：

  10.1021/ja2065158

文献信息

• Activation of carboxyl groups by diphenyl 2-oxo-3-oxazolinylphosphonate
  作者：Takehisa Kunieda、Tsunehiko Higuchi、Yoshihiro Abe、Masaaki Hirobe

  DOI：10.1016/s0040-4020(01)91572-8

  日期：1983.1

  sphonate [DPPOx] has been newly introduced as a carboxyl-activating reagent which permits a facile direct preparation of 3-acyl-2-oxazolones and amides including peptides from a wide variety of carboxylic acids The 3-acyl-2-oxazolides also serve as versatile reactive agents for highly chemoselective acyl-transfer to the nucleophilic species such as amines, alcohols and thiols, providing convenient

  描述了2-恶唑酮部分作为优异的新离去基团的合成效用。基于杂环的这种功能，新引入了2-氧代-3-恶唑啉基膦酸二苯酯[DPPOx]作为羧基活化剂，可以轻松地直接制备3-酰基-2-恶唑酮和酰胺，包括各种羧酸3-酰基-2-恶唑内酯还用作通用的反应剂，可高度化学选择性地将酰基转移至亲核物质，例如胺，醇和硫醇，为酰胺，酯和硫醇的制备提供了便捷且高产的途径酯在温和的条件下。它们也是酮和醇的有用中间体。
• Processes for forming amide bonds and compositions related thereto
  申请人：Liebeskind Lanny S.

  公开号：US08921599B2

  公开（公告）日：2014-12-30

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  该公开涉及生产酰胺键的方法及相关试剂。在某些实施例中，该公开涉及通过混合O-硅烷基硫酸酯和胺在条件下生产酰胺的方法。在另一实施例中，该公开涉及混合硫酸酯、硅基化剂和胺在条件下形成酰胺。
• Investigating Bicyclobutane–Triazolinedione Cycloadditions as a Tool for Peptide Modification
  作者：Brett D. Schwartz、Aidan P. Smyth、Philippe E. Nashar、Michael G. Gardiner、Lara R. Malins

  DOI：10.1021/acs.orglett.1c04071

  日期：2022.2.18

  cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptide-derived triazolinediones that undergo cycloaddition reactions to afford novel peptide conjugates. The additive-free and fully atom-economical nature of the transformation is a promising starting point for

  酰基双环丁烷与多种三唑啉二酮试剂进行应变促进的环加成反应。正交保护的 urazole 结构单元的合成使得能够轻松制备氨基酸和肽衍生的三唑啉二酮，这些三唑啉二酮经历环加成反应以提供新型肽缀合物。转化的无添加剂和完全原子经济的性质是将该环加成反应推广到生物分子功能化的有希望的起点。
• Synthesis of [1,2,4]Triazolo[4,3-<i>a</i>]piperazin-6-ones: An Approach to the Triazole-Fused Ketopiperazine Scaffold
  作者：Khoubaib Ben Haj Salah、Baptiste Legrand、Mathieu Bibian、Emmanuel Wenger、Jean-Alain Fehrentz、Séverine Denoyelle

  DOI：10.1021/acs.orglett.8b01112

  日期：2018.6.1

  stereoconservative synthesis to access the triazole-fused ketopiperazine (TKP) scaffold is presented. This underexplored platform offers a wide range of structural modulations with several points of diversity and chiral centers. A series of [1,2,4]triazolo[4,3-a]piperazin-6-ones was synthesized from optically pure dipeptides. The methodology was then successfully applied to access the pyrrolo[1,2-a]triazolo[3,4-c]piperazin-6-one

  提出了立体保守的合成，以接近三唑融合的酮哌嗪（TKP）支架。这个开发不足的平台可提供多种结构调制，并具有多个多样性点和手性中心。从光学纯的二肽合成了一系列[1,2,4]三唑并[4,3 - a ]哌嗪-6-。该方法然后成功地应用于访问吡咯并[1,2- a ]三唑并[3,4- c ]哌嗪-6-一三轮车。重要的是，代表性TKP的晶体结构证实在合成路线中手性中心的构型是受控的，并且取决于取代基的性质和在TKP支架上的位置有利于描述取代基的取向。
• A new reagent for activating carboxyl groups: diphenyl 2-oxo-3-oxazolinylphosphonate
  作者：Takehisa Kunieda、Yoshihiro Abe、Tsunehiko Higuchi、Masaaki Hirobe

  DOI：10.1016/s0040-4039(01)90289-8

  日期：1981.1