Boc-(L)-Trp-Gly-OH | 25691-58-1

• 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-(L)-Trp-Gly-OH
• 英文别名: [(2S)-3-(1H-indol-3-yl)-2-(t-butoxycarbonylamino)propanoylamino]acetic acid；Boc-Trp-Gly；2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetic acid
• CAS: 25691-58-1
• 化学式: C₁₈H₂₃N₃O₅
• 分子量: 361.398
• InChiKey: LEKPYENKNYAOTB-AWEZNQCLSA-N

物化性质

• 熔点：
  211-213 °C
• 沸点：
  693.4±55.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-(L)-Trp-Gly-OH 在 三乙胺 作用下， 生成 N-(tert-butoxycarbonyl)-L-tryptophylglycyl-L-aspartyl-L-phenylalanine amide
  参考文献：
  名称：

  Synthesis and binding affinities of analogs of cholecystokinin-(30-33) as probes for central nervous system cholecystokinin receptors

  摘要：

  CCK-30-33 has been identified as the minimum fragment of CCK with nanomolar affinity for the central CCK receptors, as assayed by displacement of [3H]-Boc-beta-alanyl-CCK-30-33 (pentagastrin) in homogenized mouse cerebral cortex. Examination of binding using this assay in the two series Boc-Trp-X-Phe-NH2 when X = Met-Asp (Boc-CCK-30-33), Gly-Asp, Met-Gly, and Gly-Gly and when X = (CH2)n (n = 0-4) reveals that modification of the tetrapeptide reduces affinity to a maximum of micromolar affinity (Boc-Trp-Gly-Asp-Phe-NH2; Ki = 2 X 10(-6) M), whereas in the series when n = 0 and 2 pentamolar affinity is still retained (Boc-Trp-Phe-NH2, Ki = 7 X 10(-5) M; Boc-Trp NH CH2-CH2-CO-Phe-NH2, Ki = 3 X 10(-5) M). Modification of the tetrapeptide CCK-30-33 reduces affinity 1000-fold, whereas di- and tripeptide fragments are identified that reduce affinity only a further 10-fold. This structure-activity relationship establishes a basis to design "peptoid" analogues of CCK that have therapeutic potential.

  DOI：

  10.1021/jm00387a027
• 作为产物：
  描述：

  N-叔丁氧羰基-L-色氨酸 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 Boc-(L)-Trp-Gly-OH
  参考文献：
  名称：

  Synthesis and binding affinities of analogs of cholecystokinin-(30-33) as probes for central nervous system cholecystokinin receptors

  摘要：

  CCK-30-33 has been identified as the minimum fragment of CCK with nanomolar affinity for the central CCK receptors, as assayed by displacement of [3H]-Boc-beta-alanyl-CCK-30-33 (pentagastrin) in homogenized mouse cerebral cortex. Examination of binding using this assay in the two series Boc-Trp-X-Phe-NH2 when X = Met-Asp (Boc-CCK-30-33), Gly-Asp, Met-Gly, and Gly-Gly and when X = (CH2)n (n = 0-4) reveals that modification of the tetrapeptide reduces affinity to a maximum of micromolar affinity (Boc-Trp-Gly-Asp-Phe-NH2; Ki = 2 X 10(-6) M), whereas in the series when n = 0 and 2 pentamolar affinity is still retained (Boc-Trp-Phe-NH2, Ki = 7 X 10(-5) M; Boc-Trp NH CH2-CH2-CO-Phe-NH2, Ki = 3 X 10(-5) M). Modification of the tetrapeptide CCK-30-33 reduces affinity 1000-fold, whereas di- and tripeptide fragments are identified that reduce affinity only a further 10-fold. This structure-activity relationship establishes a basis to design "peptoid" analogues of CCK that have therapeutic potential.

  DOI：

  10.1021/jm00387a027

文献信息

• Synthetic studies on novel benzimidazolopeptides with antimicrobial, cytotoxic and anthelmintic potential
  作者：Rajiv Dahiya、Devender Pathak

  DOI：10.1016/j.ejmech.2006.11.015

  日期：2007.6

  presence of cupric chloride. The coupling of compounds 5-8 with different amino acid ester hydrochlorides/dipeptide/tripeptide/tetrapeptide methyl esters afforded novel benzimidazolopeptide derivatives 5a-f, 6a-h, 7a-g and 8a-g. The structures of all newly synthesized compounds were established on the basis of analytical, IR, (1)H NMR, (13)C NMR and mass spectral data. Selected peptide ester derivatives were

  在氯化铜的存在下，通过5,6-二甲基-6硝基硝基苯并咪唑与重氮化的取代/未取代的氨基苯甲酸相互作用，合成了四个取代的苯并咪唑基-苯甲酸/水杨酸5-8。将化合物5-8与不同的氨基酸酯盐酸盐/二肽/三肽/四肽甲酯偶联，得到新的苯并咪唑并肽衍生物5a-f，6a-h，7a-g和8a-g。所有新合成的化合物的结构都是基于分析，IR，（1）H NMR，（13）C NMR和质谱数据确定的。通过使用氢氧化锂（LiOH）进一步水解选定的肽酯衍生物，得到相应的酸衍生物5b（a）-d（a​​），6e（a）-g（a），7c（a）-e（a）和8e （a）-g（a）。筛选所有肽衍生物的抗微生物，驱虫和细胞毒性活性。几乎所有新合成的苯并咪唑类肽对所有三种earth均表现出中等至良好的驱虫活性，对病原性真菌白色念珠菌和黑曲霉，革兰氏阴性细菌铜绿假单胞菌和大肠杆菌具有良好的抗菌活性。化合物8g和8g（a）对道尔顿氏淋巴瘤腹
• [EN] CONTINUOUS, SOLVENT-FREE AND NON-ENZYMATIC PEPTIDE SYNTHESIS BY REACTIVE EXTRUSION<br/>[FR] SYNTHÈSE DE PEPTIDES CONTINUE, SANS SOLVANT ET NON ENZYMATIQUE PAR EXTRUSION RÉACTIVE
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2019158506A1

  公开（公告）日：2019-08-22

  The present disclosure relates to A a continuous, solvent-free and non-enzymatic method for synthesizing a compound of formula (I): Ra-POLYPEP-Rc (I) wherein: POLYPEP is a poly-amino acid compound, Ra and Rc are as specified in the disclosure, which method comprises the steps of: a) feeding an extrusion reactor with (1) a compound of formula (II) Ra-PEPNt-Rg (II) wherein; PEPNt is a mono- or a poly-aminoacid compound, Ra and Rg are as specified in the disclosure, and (2) a compound of formula (III) H-PEPCt-Rc (III) wherein: PEPCt is a mono- or a poly-amino acid compound, and Rc is as defined in the disclosure in the absence of any solvent, so that the compound of formula (II) and the compound of formula (III) react together for generating a compound of formula (I), and b) collecting the compound of formula (I) from the extrusion reactor.

  本公开涉及一种连续、无溶剂和非酶法合成化合物的方法，其化学式为（I）：Ra-POLYPEP-Rc（I），其中：POLYPEP是一种多氨基酸化合物，Ra和Rc如本公开所述，该方法包括以下步骤：a）将挤压反应器中供给具有化学式（II）Ra-PEPNt-Rg（II）的化合物，其中：PEPNt是一种单氨基酸或多氨基酸化合物，Ra和Rg如本公开所述，并且（2）具有化学式（III）H-PEPCt-Rc（III）的化合物，其中：PEPCt是一种单氨基酸或多氨基酸化合物，Rc如本公开所定义，在无溶剂的情况下，使化学式（II）的化合物和化学式（III）的化合物相互反应生成化学式（I），b）从挤压反应器中收集化学式（I）的化合物。
• Amino acid derivatives, IX [1]: synthesis and antimicrobial evaluation of α-amino acid esters bearing a tryptophane side chain
  作者：Ahmed Hameurlaine、Wael A. El-Sayed、Adel A.-H. Abdel-Rahman

  DOI：10.1007/s00706-008-0952-y

  日期：2008.12

  A series of peptide and dipeptide derivatives conjugated with a tryptophane residue were synthesized. The prepared compounds were tested for antimicrobial activity against four different bacterial species displaying different degrees of antibacterial activities or inhibitory actions.
• Synthesis and binding affinities of analogs of cholecystokinin-(30-33) as probes for central nervous system cholecystokinin receptors
  作者：David C. Horwell、Andrew Beeby、Colin R. Clark、John Hughes

  DOI：10.1021/jm00387a027

  日期：1987.4

  CCK-30-33 has been identified as the minimum fragment of CCK with nanomolar affinity for the central CCK receptors, as assayed by displacement of [3H]-Boc-beta-alanyl-CCK-30-33 (pentagastrin) in homogenized mouse cerebral cortex. Examination of binding using this assay in the two series Boc-Trp-X-Phe-NH2 when X = Met-Asp (Boc-CCK-30-33), Gly-Asp, Met-Gly, and Gly-Gly and when X = (CH2)n (n = 0-4) reveals that modification of the tetrapeptide reduces affinity to a maximum of micromolar affinity (Boc-Trp-Gly-Asp-Phe-NH2; Ki = 2 X 10(-6) M), whereas in the series when n = 0 and 2 pentamolar affinity is still retained (Boc-Trp-Phe-NH2, Ki = 7 X 10(-5) M; Boc-Trp NH CH2-CH2-CO-Phe-NH2, Ki = 3 X 10(-5) M). Modification of the tetrapeptide CCK-30-33 reduces affinity 1000-fold, whereas di- and tripeptide fragments are identified that reduce affinity only a further 10-fold. This structure-activity relationship establishes a basis to design "peptoid" analogues of CCK that have therapeutic potential.