Boc-Ser(Bzl)-OH | 78545-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Boc-Ser(Bzl)-OH
• 英文别名: Boc-Ser(Bzl)；(2S)-3-benzoyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 78545-07-0
• 化学式: C₁₅H₁₉NO₆
• 分子量: 309.319
• InChiKey: NAQTVMQCLGUVMO-NSHDSACASA-N

物化性质

• 沸点：
  494.3±40.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Boc-Ser(Bzl)-OH 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到
  参考文献：
  名称：

  Suresh Babu; Gopi; Ananda, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2000, vol. 39, # 5, p. 384 - 386

  摘要：

  DOI：
• 作为产物：
  描述：

  N-重氮基氨基甲酸叔-丁基酯 、 O-benzoyl-L-serine 生成 Boc-Ser(Bzl)-OH
  参考文献：
  名称：

  Schwenzer,B. et al., Journal fur praktische Chemie (Leipzig 1954), 1979, vol. 321, p. 1007 - 1016

  摘要：

  DOI：

文献信息

• 2-Hydroxyimino-2-phenylacetonitrile active esters in peptide synthesis
  作者：Wiktor Koziołkiewicz、Anna Janecka

  DOI：10.1016/s0040-4039(00)99378-x

  日期：1989.1

  A number of 2-hydroxyimino-2-phenylacetonitrile esters of acylamino acids have been synthesized. These compounds react readily with amino acid or peptide esters to elongate the peptide chain.

  已经合成了许多酰基氨基酸的2-羟基亚氨基-2-苯基乙腈酯。这些化合物容易与氨基酸或肽酯反应以延长肽链。
• Minimum Structure of Diapause Hormone Required for Biological Activity
  作者：Kunio IMAI、Toshikazu NOMURA、Hirotaka KATSUZAKI、Takashi KOMIYA、Okitsugu YAMASHITA

  DOI：10.1271/bbb.62.1875

  日期：1998.1

  Diapause hormone is a 24-amino acid peptide amide, and its C-terminal penta-peptide amide structure of FGPRL-NH2 is believed to be essential for biological activity. The penta-peptide amide, the shorter peptide amides, and their derivatives and analogs were prepared to determine the minimal structure for biological activity. The C-terminal amide group of the penta-peptide amide was not replaced with the other functional groups, but Gly, the 4th amino acid from the C terminal, could be substituted with an other amino acid while maintaining the biological activity. The shorter peptide amide, PRL-NH2, possessed low but significant activity, indicating the minimum structure of diapause hormone. By modifying its N-terminal, the aromatic ring of Phe is shown to enhance the activity of PRL-NH2.

  滞育激素是一种由24个氨基酸组成的肽酰胺，其C端五肽酰胺结构FGPRL-NH2被认为对生物活性至关重要。为了确定生物活性所需的最小结构，制备了五肽酰胺、较短的肽酰胺及其衍生物和类似物。五肽酰胺的C端酰胺基团未被其他功能基团替代，但Gly，即从C端起第四个氨基酸，可以在保持生物活性的前提下被其他氨基酸替换。较短的肽酰胺PRL-NH2具有较低但显著的活性，表明这是滞育激素的最小结构。通过修饰其N端，发现苯环对活性的增强作用，揭示了Phe环在PRL-NH2活性提升中的作用。
• Rapid Access to ω-Conotoxin Chimeras using Native Chemical Ligation
  作者：Gene Hopping、Richard J. Lewis、Paul F. Alewood

  DOI：10.1071/ch09216

  日期：——

  Grafting different regions of related peptides together to form a single protein chimera is a valuable tool in rapidly elucidating regions of activity or selectivity in peptides and proteins. To conveniently evaluate the contributions of the N- and C-terminal segments of ω-conotoxins CVID and MVIIC to activity, we employed native chemical ligation in CVID-MVIIC chimera design. Assembly of these peptide segments via the ligation method improved overall yield and coupling efficiency, with no difficult sequences encountered in contrast to the traditional full-length chain assembly of CVID. Radio-ligand binding assays revealed regions of importance for receptor recognition.

  将相关多肽的不同区域嫁接在一起形成单个蛋白质嵌合体是快速阐明多肽和蛋白质活性或选择性区域的重要工具。为了方便地评估ω-康毒素CVID和MVIIC的N端和C端对活性的贡献，我们在CVID-MVIIC嵌合体设计中采用了原生化学连接法。与传统的 CVID 全长链组装相比，通过连接法组装这些肽段提高了总体产量和耦合效率，而且没有遇到困难序列。无线电配体结合试验揭示了受体识别的重要区域。
• Solid phase synthesis of a prototype of a new class of biomimetic receptors for anionic carbohydrates
  作者：Carsten Schmuck、Maija Heller

  DOI：10.1039/b613660e

  日期：——

  A solid phase synthesis for a new biomimetic receptor 1 was developed. First binding studies show that 1 binds anionic carbohydrates such as glucose-1-phosphate and cAMP with association constants in the lower millimolar range in 20% buffered water in DMSO using both polar and apolar interactions.

  开发了一种新型仿生受体1的固相合成方法。初步结合研究显示，受体1能够通过极性和非极性相互作用，在含20%水的二甲基亚砜缓冲溶液中，与阴离子碳水化合物如葡萄糖-1-磷酸和cAMP以较低的毫摩尔范围结合常数相结合。
• Synthesis, anti-inflammatory activity and molecular docking studies of 2,5-diarylfuran amino acid derivatives
  作者：Hélio A. Stefani、Giancarlo V. Botteselle、Julio Zukerman-Schpector、Ignez Caracelli、Denis da Silva Corrêa、Sandra H.P. Farsky、Isabel D. Machado、José R. Santin、Cristina B. Hebeda

  DOI：10.1016/j.ejmech.2011.10.018

  日期：2012.1

  A series of 2,5-diaryl substituted furans functionalized with several amino acids were synthesized and evaluated as the cyclooxygenases COX-1 and COX-2 enzymes inhibitors. The proline-substituted compound inhibited PGE2 secretion by LPS-stimulated neutrophils, suggesting selectivity for COX-2. Molecular docking studies in the binding site of COX-2 were performed.

  合成了一系列被几个氨基酸官能化的2,5-二芳基取代的呋喃，并作为环氧合酶COX-1和COX-2酶的抑制剂进行了评估。脯氨酸取代的化合物抑制LPS刺激的中性粒细胞分泌PGE 2，表明对COX-2具有选择性。在COX-2的结合位点进行了分子对接研究。