glycine 9-fluorenylmethyl ester | 124927-88-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: glycine 9-fluorenylmethyl ester
• 英文别名: glycine 9-fluorenylmethyl ester hydrochloride；Fmoc-O-glycine；Fmoc-Gly-OH；9H-fluoren-9-ylmethyl 2-aminoacetate
• CAS: 124927-88-4
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: XHYUDJFILRMEQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 glycine 9-fluorenylmethyl ester 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  Click activated protodrugs against cancer increase the therapeutic potential of chemotherapy through local capture and activation

  摘要：

  点击激活的原型药物抗癌（CAPAC）平台利用点击化学在靶点直接激活细胞毒性药物，最大限度减少毒性，克服了传统化疗和传统靶向治疗的局限性。

  DOI：

  10.1039/d0sc06099b
• 作为产物：
  描述：

  9-芴甲醇 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 48.5h， 生成 glycine 9-fluorenylmethyl ester
  参考文献：
  名称：

  4-(9-Fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH):  A New Chromophoric Reagent for Quantitative Monitoring of Solid-Phase Aldehydes^1-3

  摘要：

  A direct method for quantifying solid-phase aldehydes has been developed, using a new reagent, 4-(9-fluorenylmethyloxycarbonyl)phenylhydrazine (FmPH). The FmPH reagent was synthesized in three steps (24% overall yield) from commercially available p-hydrazinobenzoic acid. Resin-bound aldehydes reacted quantitatively with FmPH, in the presence of trimethylorthoformate (TMOF) as a dehydrating agent, to form a highly conjugated, immobilized FmPH-hydrazone. Next, mild treatment of the hydrazone with an excess of piperidine-N,N-dimethylformamide (1:1) released the piperidine-dibenzofulvene adduct chromophore (epsilon(301nm) = 7800 M-1 cm(-1)) from the support. FmPH quantitation of aldehydes proved to be a straightforward, sensitive, and reproducible technique for monitoring resin-bound aldehydes [albeit insufficiently reactive to allow reliable quantification of ketones]. The FmPH aldehyde assay is applicable to a range of solid supports, as demonstrated specifically for poly(ethylene glycol)-polystyrene (PEG-PS), aminomethylpolystyrene (AMP), and cross-linked ethoxylate acrylate resin (CLEAR).

  DOI：

  10.1021/jo049830b

文献信息

• PEPTIDOMIMETICS POSSESSING PHOTO-CONTROLLED BIOLOGICAL ACTIVITY
  申请人：KARLSRUHER INSTITUT FÜR TECHNOLOGIE

  公开号：US20170051017A1

  公开（公告）日：2017-02-23

  The present invention relates to pharmaceutically and/or diagnostically active compounds, in particular peptide analogues (peptidomimetics), which can be reversibly controlled between an active and an inactive state by irradiation with light of different wavelengths. The present invention further relates to an intermediate compound usable in the manufacture of such pharmaceutically and/or diagnostically active compounds, as well as a manufacturing method thereof.

  本发明涉及药理学和/或诊断上有活性的化合物，特别是肽类似物（肽模拟物），这些化合物可以通过不同波长的光照在活性状态和非活性状态之间进行可逆控制。本发明还涉及一种可用于制造此类药理学和/或诊断上有活性的化合物的中间体化合物，以及其制造方法。
• Concise Total Synthesis of the Thiazolyl Peptide Antibiotic GE2270 A
  作者：Oscar Delgado、H. Martin Müller、Thorsten Bach

  DOI：10.1002/chem.200701823

  日期：2008.3.7

  after metalation to a zinc reagent by another Negishi cross-coupling (48 %). Decisive step of the whole sequence was the macrocyclization to a 29-membered macrolactam, which was conducted as an intramolecular Stille cross-coupling occurring at C-2 of the pyridine core and providing the desired product in 75 % yield. The required stannane was obtained by amide bond formation (87 %) between a complex dithiazole

  由N-叔丁氧羰基保护的缬氨酸以最长的20步线性序列合成了有效的抗生素噻唑基肽GE2270 A，总产率为4.8％。关键策略是通过从2,6-二溴-3-碘吡啶开始的连续交叉偶联反应组装2,3,6-三取代吡啶核。通过3-锌的2，6-二溴吡啶的Negishi交叉偶联将完整的Southern片段安装在三噻唑的2-碘噻唑末端（87％）。在通过另一个Negishi交叉偶联金属化成锌试剂后，以截短的2-溴噻唑-4-羧酸叔丁酯形式引入代表分子北部的C-6处的取代基。整个序列的决定性步骤是将大环化成29元大环内酰胺，这是通过发生在吡啶核的C-2处的分子内Stille交叉偶联进行的，以75％的收率提供所需的产物。通过在代表GE2270 A东部的复杂二噻唑片段与3,6-二取代的2-溴吡啶之间的酰胺键形成（87％）获得所需的锡烷。最终步骤包括将丝氨酸-脯氨酸酰胺二肽附着到分子的北部（65％），形成恶唑啉环和甲硅烷基醚脱保护（总体占55％）。
• Breast Tumor Targeting in Mice Bearing 4T1 Tumor with Labeled CXCR4 Antagonist Analogue
  作者：Azadeh Mikaeili、Mostafa Erfani、Mostafa Goudarzi、Omid Sabzevari

  DOI：10.1007/s10989-021-10264-2

  日期：2021.12

  over-expressed in many type of solid tumors and metastasis in which breast tumor is one of them. A CXCR4 targeted peptide was prepared and labeled with 99mTc. Subsequently, receptor binding internalization, in vivo tumor uptake and biodistribution were assessed. The receptor binding internalization rate was evaluated using 4T1 breast tumor cells. BALB/c female mice bearing 4T1 tumors were employed for investigation

  趋化因子受体属于 G 蛋白偶联的细胞表面受体。CXCR4作为趋化因子受体在许多类型的实体瘤和转移瘤中过度表达，其中乳腺肿瘤就是其中之一。制备了 CXCR4 靶向肽并用99m标记吨。随后，评估了受体结合内化、体内肿瘤摄取和生物分布。使用 4T1 乳腺肿瘤细胞评估受体结合内化率。使用带有 4T1 肿瘤的 BALB/c 雌性小鼠来研究放射性偶联物的生物分布。以> 95% 的标记产率获得放射性缀合物。达到的最高比活为 123 MBq/nmol。体外细胞摄取测试导致特异性内化到 4T1 细胞中（2 小时平均 1.90 ± 0.12% 的总添加量）。动物生物分布数据显示注射后 30 分钟后肿瘤吸收率为 1.18 ± 0.11% ID/g。我们的研究结果表明，标记的肽可以成为乳腺肿瘤成像的合适候选者。
• Synthesis of a dendron and dendrimer consisting of MALDI matrix like branching units
  作者：Hendrik Neubert、Andrew T. Kicman、David A. Cowan、Sukhvinder S. Bansal

  DOI：10.1016/s0040-4039(02)01522-8

  日期：2002.9

  intermediates of the monomer synthesis were shown to function as MALDI matrices. A second-generation dendron was assembled on a solid support employing an N-to-C directed convergent synthetic strategy. Coupling of the dendrons with a trivalent core molecule resulted in a second generation dendrimer.

  描述了一种新颖的树枝状和树枝状大分子的合成方法，该方法在基质辅助激光解吸/电离质谱（MALDI MS）中具有潜在的应用。树枝状大分子支化单元设计成与MALDI MS中使用的基于肉桂酸的基质具有结构相似性。通过引入第二个丙烯酸侧链将支化结合到结构中。单体合成的某些中间体已显示出可作为MALDI基质的功能。第二代树枝状分子采用N-C定向聚合合成策略组装在固体支持物上。树突与三价核心分子的偶联产生第二代树状聚合物。
• [EN] CELL PERMEABLE PEPTIDOMIMETIC MACROCYCLES<br/>[FR] MACROCYCLES PEPTIDOMIMÉTIQUES PERMÉABLES AUX CELLULES
  申请人：AILERON THERAPEUTICS INC

  公开号：WO2017205786A1

  公开（公告）日：2017-11-30

  The present invention provides peptidomimetic macrocycles and methods for selecting peptidomimetic macrocycles and methods of using such peptidomimetic macrocycles for the treatment of disease.

  本发明提供了肽类模拟宏环以及选择肽类模拟宏环的方法和使用这种肽类模拟宏环治疗疾病的方法。