Boc-Ala-Ala-Phe-OH | 56133-10-9

• 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-Ala-Ala-Phe-OH
• 英文别名: t-Butyloxycarbonyl-alanyl-alanyl-phenylalanine；(2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoyl]amino]-3-phenylpropanoic acid
• CAS: 56133-10-9
• 化学式: C₂₀H₂₉N₃O₆
• 分子量: 407.467
• InChiKey: KFAZLNSFYNGMEM-YDHLFZDLSA-N

物化性质

• 沸点：
  689.8±55.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ala-Ala-Phe-OH 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 TFA*H-Ala-Ala-Phe-Lys(Z)-OMe
  参考文献：
  名称：

  Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function

  摘要：

  Fourteen new functionally active amino acid and peptide derivatives of the antibiotics tylosin, desmycosin, and 5-O-mycaminosyltylonolide were synthesized in order to study the interaction of the growing polypeptide chain with the ribosomal tunnel. The conjugation of various amino acids and peptides with a macrolide aldehyde group was carried out by two methods: direct reductive amination with the isolation of the intermediate Schiff bases or through binding via oxime using the preliminarily obtained derivatives of 2-aminooxy-acetic acid.

  DOI：

  10.1134/s1068162010020159
• 作为产物：
  描述：

  Benzyl (2S)-2-{(2S)-2-[(2S)-2-(tert-butoxycarbonylamino)propionylamino]propionylamino}-3-phenylpropionate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 Boc-Ala-Ala-Phe-OH
  参考文献：
  名称：

  [EN] TREATMENT AND DIAGNOSIS OF IMMUNE DISORDERS RELATING TO ABERRANT IMMUNE CELLS
  [FR] TRAITEMENT ET DIAGNOSTIC DE TROUBLES IMMUNITAIRES ASSOCIÉS À DES CELLULES IMMUNITAIRES ABERRANTES

  摘要：

  Disclosed are compositions and methods of treating and diagnosing immune-related disorders characterized by the presence of aberrant immune cells that over-express certain proteins or that express a protein not expressed on normal immune cells.

  公开号：

  WO2023014360A1

文献信息

• Fluorescent probe for high-sensitivity pancreatic fluid detection, and method for detecting pancreatic fluid
  申请人：THE UNIVERSITY OF TOKYO

  公开号：US09506102B2

  公开（公告）日：2016-11-29

  A fluorescent probe for detecting pancreatic fluid containing a compound or salt thereof represented by formula (I) below. (In the formula, A represents an amino acid residue or N-substituted amino acid residue, with A forming an amide bond with the adjacent NH in the formula; R1 represents a hydrogen atom or 1 to 4 same or different substituent groups that bond with a benzene ring; R2, R3, R4, R5, R6, and R7 each independently represent a hydrogen atom, a hydroxyl group, an alkyl group, or a halogen atom; R8 and R9 each independently represent a hydrogen atom or an alkyl group; and X represents a C1-C3 alkylene group).

  下面是表示为以下公式（I）的化合物或其盐的胰液检测用荧光探针。 （在公式中，A代表氨基酸残基或N-取代氨基酸残基，其中A与公式中相邻的NH形成酰胺键；R1代表氢原子或与苯环结合的1至4个相同或不同的取代基团；R2、R3、R4、R5、R6和R7分别独立地代表氢原子、羟基、烷基或卤素原子；R8和R9分别独立地代表氢原子或烷基；X代表C1-C3烷基基团）。
• General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis
  作者：Andrea Temperini、Francesca Piazzolla、Lucio Minuti、Massimo Curini、Carlo Siciliano

  DOI：10.1021/acs.joc.7b00173

  日期：2017.5.5

  A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.

  开发了一种温和，实用和简单的方法，用于从几种酸酐和二苯基二硒化物合成苯基硒酸酯。这种无过渡金属的方法可以直接进入可存储的Fmoc-氨基酸硒酸酯，它们是有效的化学选择性酰化试剂。说明了在寡肽合成中的应用。
• Furan-Based Locked<i>Z</i>-Vinylogous γ-Amino Acid Stabilizing Protein α-Turn in Water-Soluble Cyclic α₃γ Tetrapeptides
  作者：Yarkali Krishna、Shrikant Sharma、Ravi S. Ampapathi、Dipankar Koley

  DOI：10.1021/ol5002126

  日期：2014.4.18

  Described here is the design, synthesis, and conformational analysis of cyclic tetrapeptides (CTPs) with α3γ architecture containing a furan-based locked Z-vinylogous amino acid (Vaa). This unnatural amino acid locks into a γ-turn that induces type IαRS-turn in the CTPs. Stabilized by a 13-membered intramolecular H-bond, these CTPs show robust conformation in water and aprotic solvent irrespective

  这里描述的是设计，合成和环状四肽（CTP的）与α的构象分析3含有呋喃基锁定γ架构Ž -vinylogous氨基酸（VAA）。这个非天然氨基酸锁入一个γ-转弯诱导型Iα RS转角在的CTP。这些CTP通过13元的分子内H键稳定，无论在水和非质子溶剂中的构象如何，均不依赖于由α-氨基酸组成的三肽序列。
• Peptide derivatives of tylosin-related macrolides
  作者：G. A. Korshunova、N. V. Sumbatyan、N. V. Fedorova、I. V. Kuznetsova、A. V. Shishkina、A. A. Bogdanov

  DOI：10.1134/s1068162007020033

  日期：2007.3

  Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O=mycaminosyltylonolide were developed to study the conformation and topography of the nascent peptide chain in the ribosome tunnel using specially designed peptide derivatives of macrolide antibiotics. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed

  开发了基于泰乐菌素相关的大环内酯类去霉素和 O=mycaminosyltylonolide 的模型化合物的合成方法，以使用专门设计的大环内酯类抗生素的肽衍生物研究核糖体隧道中新生肽链的构象和形貌。开发了一种在mycinose 羟基上选择性溴乙酰化脱粘菌素的方法，该方法涉及mycaminose 的初步乙酰化。抗生素的 4″-溴乙酰基衍生物与二肽 Boc-Ala-Ala-OH 和六肽 MeOTr-Gly-Pro-Gly-Pro-Gly-Pro-OH 的铯盐反应生成相应的肽衍生物去霉菌素。受保护的肽 Boc-Ala-Ala-OH、Boc-Ala-Ala-Phe-OH 和 Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH 与 O-mycaminosyltylonolide 的 C23-羟基缩合。
• Endothiopeptide inhibitors of HIV-1 protease
  作者：Shao Yao、Reena Zutshi、Jean Chmielewski

  DOI：10.1016/s0960-894x(98)00100-0

  日期：1998.3

  Endothiopeptide inhibitors of HIV-1 protease were synthesized by chemical and enzymatic methods to individually replace each backbone amide bond in 1 with a thioamide-linkage. Interestingly, agent 7, which contains a thioamide-linkage between the P-2' and P-3' positions of 1, was the most potent, competitive inhibitor of HIV-1 protease with a K-i of 3.4 mu M. (C) 1998 Elsevier Science Ltd. All rights reserved.