N-tert-butyloxycarbonyl-O-tert-butyloxycarbonyl-L-tyrosyl-glygylglicine | 88829-53-2

• 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: N-tert-butyloxycarbonyl-O-tert-butyloxycarbonyl-L-tyrosyl-glygylglicine
• 英文别名: N,O-di-tert-butyloxycarbonyl-L-tyrosylglycylglycine；Boc-Tyr(Boc)-Gly-Gly-OH；2-[[2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-[4-[(2-methylpropan-2-yl)oxycarbonyloxy]phenyl]propanoyl]amino]acetyl]amino]acetic acid
• CAS: 88829-53-2
• 化学式: C₂₃H₃₃N₃O₉
• 分子量: 495.53
• InChiKey: HHFGUSHOEZCEOY-INIZCTEOSA-N

物化性质

• 熔点：
  98-101 °C
• 沸点：
  775.9±60.0 °C(Predicted)
• 密度：
  1.238±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  169.36
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  N-tert-butyloxycarbonyl-O-tert-butyloxycarbonyl-L-tyrosyl-glygylglicine 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 苯甲醚 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.53h， 生成 [3-({2-[(S)-2-(2-{2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-acetylamino}-acetylamino)-3-phenyl-propionylamino]-4-methylsulfanyl-butyrylamino}-methyl)-adamantan-1-yl]-acetic acid
  参考文献：
  名称：

  Tumor-Cell-Targeted Methionine-enkephalin Analogues Containing Unnatural Amino Acids:  Design, Synthesis, and in Vitro Antitumor Activity

  摘要：

  A series of new peptides (8-25) containing different unnatural amino acids of the adamantane type (1-6), was synthesized. Possible cytotoxic activity on human cervical adenocarcinoma ( HeLa), larynx carcinoma (HEp-2), colon carcinomas (HT-29, Caco-2), poorly differentiated cells from lymph node metastasis of colon carcinoma (SW-620), mammary gland adenocarcinoma (MCF-7), and melanoma (HBL) cells were tested by the MTT assay. The results were compared with the effect of methionine-enkephalin (Tyr-GlyGly-Phe-Met, or opioid growth factor, OGF), and its shorter N-terminal fragments. Peptide analogues containing CRR-dialkylated glycine (Aaa1, 1) or CR-alkylated glycine (Aaa2, 2) amino acid residues showed antitumor activity against melanoma, larynx carcinoma, colon carcinomas, and colon metastasis cell lines in vitro. The pentapeptide Tyr-(R,S)-Aaa2-Gly-Phe-Met (18) was the most effective analogue especially against the most antitumor drug-resistant cell lines HEp-2 and SW-620. Apoptosis as a mode of cell death was confirmed in these tumor cells after exposure to pentapeptide 18.

  DOI：

  10.1021/jm051026+
• 作为产物：
  描述：

  N,O-双[(叔丁氧基)羰基]-L-酪氨酸 、 双甘肽 生成 N-tert-butyloxycarbonyl-O-tert-butyloxycarbonyl-L-tyrosyl-glygylglicine
  参考文献：
  名称：

  HORVAT, S.;HORVAT, J.;KANTOCI, D.;VARGA, L., TETRAHEDRON, 45,(1989) N4, C. 4579-4584

  摘要：

  DOI：

文献信息

• Synthesis and intramolecular reactions of Tyr-Gly and Tyr-Gly-Gly related 6-O-glucopyranose esters
  作者：Lidija Varga-Defterdarović、Gorana Hrlec

  DOI：10.1016/j.carres.2003.07.011

  日期：2004.1

  6-O-(L-Tyrosylglycyl)- and 6-O-(L-tyrosylglycylglycyl)-D-glucopyranose were synthesized by condensation of the pentachlorophenyl esters of the respective di- and tripeptide with fully unprotected D-glucose. The intramolecular reactivity of the sugar conjugates was studied in pyridine-acetic acid and in dry methanol, at various temperatures and for various incubation times. The composition of the incubation

  通过各自二肽和三肽的五氯苯基酯与完全未保护的D-葡萄糖的缩合合成6-O-（L-酪氨酰糖基）-和6-O-（L-酪氨酰糖基）-D-吡喃葡萄糖。在吡啶-乙酸和无水甲醇中，在各种温度和不同的孵育时间下研究了糖缀合物的分子内反应性。通过反相HPLC方法监测孵育混合物的组成，该方法允许同时分析起始材料的消失以及重排和降解产物的出现。为了确定肽羧基的酯化对其氨基反应性的影响，进行了平行实验，其中在相同的反应条件下，将游离肽与D-葡萄糖（摩尔比为1：1和1：5）。取决于起始化合物，获得了不同类型的Amadori产物（环状和双环形式），肽的甲基酯和Tyr-Gly-二酮哌嗪。
• Facile regioselective formation of thiopeptide linkages from oligopeptides with new thionation reagents
  作者：G. Lajoie、F. Lépine、L. Maziak、B. Belleau

  DOI：10.1016/s0040-4039(00)94282-5

  日期：1983.1

  The thionation reagent 1 and the new more soluble and readily purified analogue 2 permit, in appropriate solvents, the low temperature backbone thionation of oligopeptides in a regioselective manner and in high yields.

  硫磺化试剂1和新的更易溶解且易于纯化的类似物2在适当的溶剂中允许以区域选择性的方式和高收率对寡肽进行低温主链硫磺化。
• Glycoconjugates of opioid peptides - III+. A novel regioselective synthesis of 6-O-peptidyl-d-glycopyranoses using unprotected sugars
  作者：Š. Horvat★、J. Horvat、D. Kantoci、L. Varga

  DOI：10.1016/s0040-4020(01)89092-x

  日期：——

  The primary hydroxyl groups of d-glucose and 2-acetamido-2-deoxy-d-glucose were selectively esterified by treating the free sugars with activated esters of peptides in the presence of imidazole, thus affording exclusively 6-O-peptidyl-d-glucopyranoses.

  通过在咪唑存在下用肽的活化酯处理游离糖来选择性地酯化d-葡萄糖和2-acetamido-2-deoxy-d-葡萄糖的伯羟基，从而仅得到6 - O-肽基-d-吡喃葡萄糖。