Fmoc-Phe-OH | 1175778-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Phe-OH
• 英文别名: 9H-fluoren-9-ylmethyl N-[(2S)-3-oxo-1-phenylbutan-2-yl]carbamate
• CAS: 1175778-05-8
• 化学式: C₂₅H₂₃NO₃
• 分子量: 385.463
• InChiKey: WPOAAVDGDUYSEZ-DEOSSOPVSA-N

物化性质

• 沸点：
  584.4±45.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe-OH 、 Fmoc-甘氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-Pbf-L-精氨酸 生成 Arg-Ile-Lys-Ile-Gly-Leu-Phe-NH2
  参考文献：
  名称：

  A Synthetic Approach to Develop Peptide Inhibitors Selective for Brain-Type Sodium Channels on the Basis of Pompilidotoxin Structure

  摘要：

  To develop inhibitors that are selective for brain-type sodium channels, several peptides were synthesized on the basis of pompilidotoxin structure. A peptide having N-terminal 7 amino acids and its homologs in which Phe(7) is substituted into more hydrophobic amino acids, selectively inhibit sodium current of brain-type sodium channels.

  DOI：

  10.3987/com-08-s(d)67

文献信息

• Modification of daunorubicin‐GnRH‐III bioconjugates with oligoethylene glycol derivatives to improve solubility and bioavailability for targeted cancer chemotherapy
  作者：Rózsa Hegedüs、Aline Pauschert、Erika Orbán、Ildikó Szabó、David Andreu、Andreas Marquardt、Gábor Mező、Marilena Manea

  DOI：10.1002/bip.22629

  日期：2015.5

  between the anticancer drug and the peptide-based targeting moiety, (2) peptide modification by short chain fatty acids, or (3) attachment of two anticancer drugs to the same GnRH-III derivative. Although these modifications led to more potent bioconjugates, a decrease in their solubility was observed. Here we report on the design, synthesis and biochemical characterization of daunorubicin-GnRH-III bioconjugates

  柔红霉素-GnRH-III生物共轭物最近已被开发为药物输送系统，在靶向癌症化疗中具有潜在的应用前景。为了改善其生化特性，已采取了几种策略：（1）在抗癌药和基于肽的靶向部分之间引入酶促可裂解的间隔基；（2）通过短链脂肪酸修饰肽，或（3）两种抗癌药与同一GnRH-III衍生物的连接。尽管这些修饰导致更有效的生物缀合物，但观察到它们的溶解度降低。在这里我们报告了柔红霉素-GnRH-III生物共轭物的设计，合成和生化特性的增加的溶解度，这可以通过在其结构中掺入基于低聚乙二醇的间隔基来实现。第一的，我们已经评估了基于低聚乙二醇的间隔基对仅包含一种通过GFLG四肽间隔基连接到GnRH-III靶向部分的柔红霉素的生物共轭物的溶解度，酶稳定性/降解，细胞摄取和体外细胞抑制作用的影响。此后，合成了更复杂的化合物，该化合物在GnRH-III的4位上含有两个拷贝的柔红霉素，GFLG间隔子以及Lys（nBu），并
• MONOMETHYLVALINE COMPOUNDS CAPABLE OF CONJUGATION TO LIGANDS
  申请人：DORONINA SVETLANA O.

  公开号：US20120034246A1

  公开（公告）日：2012-02-09

  Auristatin peptides, including MeVal-Val-Dil-Dap-Norephedrine (MMAE) and MeVal-Val-Dil-Dap-Phe (MMAF), were prepared and attached to Ligands through various linkers, including maleimidocaproyl-val-cit-PAB. The resulting ligand drug conjugates were active in vitro and in vivo.

  Auristatin肽包括MeVal-Val-Dil-Dap-Norephedrine (MMAE)和MeVal-Val-Dil-Dap-Phe (MMAF)，通过不同的连接剂，包括maleimidocaproyl-val-cit-PAB，制备并连接到配体上。所得的配体药物偶联物在体内外均具有活性。
• METHODS OF USING MONOMETHYLVALINE COMPOSITIONS HAVING PHENYLALANINE CARBOXY MODIFICATIONS AT THE C-TERMINUS
  申请人：Seattle Genetics, Inc.

  公开号：US20150044238A1

  公开（公告）日：2015-02-12

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) having a carboxylic acid equivalent at the C-terminal phenylalanine were prepared and attached to ligands through various linkers, including maleimidocaproyl-val-cit-PAB. The resulting ligand-drug conjugates were active in vitro and in vivo in inhibiting cell proliferation and are represented by the general structure of L v -[(LU) 0-1 -(D) 1-4 ] p wherein L- is Ligand unit; LU is a Linker unit (LU); v is 1; p is an number ranging from about 1 to about 20; and D is a drug moiety having the formula: wherein the moiety —N(R 9 )Z 1 is a phenylalanine bioisostere, wherein Z 1 is —CH(R 10 )Z 2 so that the phenylalanine bioisostere has the structure of Formula A: and wherein the substituents R 2 -R 10 , X 1 and Z 2 are as defined.

  制备了具有C端苯丙氨酸羧酸等效物的MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物，并通过各种连接剂将其连接到配体上，包括maleimidocaproyl-val-cit-PAB。所得的配体-药物偶联物在体外和体内抑制细胞增殖方面具有活性，并由以下一般结构表示：Lv-[(LU)0-1-(D)1-4]p，其中L-是配体单元；LU是连接单元（LU）；v为1；p为约1至约20的数字；D是具有以下公式的药物基团：其中，—N（R9）Z1基团是苯丙氨酸生物同构体，其中Z1是—CH（R10）Z2，以便苯丙氨酸生物同构体具有A式结构；其中取代基R2-R10、X1和Z2如定义。
• MONOMETHYLVALINE COMPOUNDS HAVING PHENYLALANINE SIDE-CHAIN MODIFICATIONS AT THE C-TERMINUS
  申请人：Seattle Genetics, Inc.

  公开号：US20130123465A1

  公开（公告）日：2013-05-16

  Auristatin peptide analogs of MeVal-Val-Dil-Dap-Phe (MMAF) are provided having C-terminal phenylalanine residue side chain replacements or modifications which are provided alone or attached to ligands through various linkers. The related conjugates can target specific cell types to provide therapeutic benefit.

  提供了MeVal-Val-Dil-Dap-Phe（MMAF）的Auristatin肽类类似物，其具有C-末端苯丙氨酸残基侧链替换或修饰，可单独提供或通过各种连接剂连接到配体上。相关的结合物可以定向特定的细胞类型，以提供治疗效益。
• Modular Synthesis of Unnatural Peptides via Rh(III)-Catalyzed Diastereoselective Three-Component Carboamidation Reaction
  作者：Christopher W. Lamartina、Cassandra A. Chartier、Sumin Lee、Neel H. Shah、Tomislav Rovis

  DOI：10.1021/jacs.2c10793

  日期：2023.1.18

  substrate scope and is compatible with a wide array of protected amino acid residues that are utilized in Fmoc solid phase peptide synthesis. The methodology is applied to the synthesis of six diastereomeric proteasome inhibitor analogs, as well as the ligation of two 10-mer oligopeptides to construct a 21-mer polypeptide with an unnatural phenylalanine residue at the center.

  在此，我们报告了一种模块化肽连接方法，该方法在温和条件下，在 Rh(III) 催化的促进下，偶联二恶唑酮、芳基硼酸和丙烯酰胺，以非对映选择性方式构建酰胺键。通过将一个肽的 C 端转化为二恶唑酮，将第二个肽的 N 端转化为丙烯酰胺，这两部分可以通过芳基硼酸桥接，在连接点构建非天然苯丙氨酸、酪氨酸和色氨酸残基其相应的d -立体中心的非对映选择性。该反应表现出优异的官能团耐受性和较大的底物范围，并且与 Fmoc 固相肽合成中使用的各种受保护的氨基酸残基兼容。该方法适用于合成六种非对映体蛋白酶体抑制剂类似物，以及连接两个 10 聚体寡肽以构建中心具有非天然苯丙氨酸残基的 21 聚体多肽。