Trt-Gly-Gly-OH | 5893-07-2

• 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: Trt-Gly-Gly-OH
• 英文别名: N-Triphenylmethyl-glycyl-glycin；N-(Triphenylmethyl)glycylglycine；2-[[2-(tritylamino)acetyl]amino]acetic acid
• CAS: 5893-07-2
• 化学式: C₂₃H₂₂N₂O₃
• 分子量: 374.439
• InChiKey: UMAMUAHGYMAHSA-UHFFFAOYSA-N

物化性质

• 熔点：
  186 °C
• 沸点：
  606.1±55.0 °C(Predicted)
• 密度：
  1.214±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  Trt-Gly-Gly-OH 在 乙醇 、 钯 作用下， 生成 双甘肽
  参考文献：
  名称：

  N-Tritylamino Acids and Peptides. A New Method of Peptide Synthesis¹

  摘要：

  DOI：

  10.1021/ja01588a027
• 作为产物：
  描述：

  N-(三苯甲基)甘氨酸 在 ammonium molybdate 、 氢氧化钾 、 双氧水 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 生成 Trt-Gly-Gly-OH
  参考文献：
  名称：

  2-（对硝基苯硫基）乙基用于肽合成中的羧基保护

  摘要：

  作为2-甲基硫基乙基的替代物，可以使用2-（对硝基苯硫基）乙基用于肽合成中的羧基保护，并且具有某些优点。该基团在转化为相应的砜后，通过用碱（在室温下为pH 10-10·5）处理而被有选择地除去。

  DOI：

  10.1039/j39690002495

文献信息

• Synthesis of Carboxymethylpullulan-Peptide-Doxorubicin Conjugates and Their Properties.
  作者：Hideo NOGUSA、Toshiro YANO、Satoshi OKUNO、Hiroshi HAMANA、Kazuhiro INOUE

  DOI：10.1248/cpb.43.1931

  日期：——

  The amino group of doxorubicin (DXR) was found to be bound to the carboxyl group of carboxymethylpullulan (CMPul) either directly or through tetrapeptide spacers, including Gly-Gly-Phe-Gly, Gly-Phe-Gly-Gly and Gly-Gly-Gly-Gly. These conjugates had DXR contents of 6.1-7.1%, with the degree of substitution of carboxymethyl groups being 0.6 per sugar moiety. These conjugates associate in phosphate-buffered saline (PBS)(pH 7.4), forming micelles with hydrophobic DXR inside and hydrophilic CMPul on the outside. The amounts of DXR released from the conjugates in the presence of rat liver lysosomal enzymes were determined by HPLC. The rate of the drug release differed among the conjugates tested. CMPul-DXR conjugate bound through Gly-Gly-Phe-Gly released 35% of its DXR over 24 h. On the other hand, CMPul-DXR conjugate without spacer released no free DXR. The antitumor effect of each conjugate in rats bearing Walker 256 was studied by monitoring the tumor weights after a single intravenous injection. Compared with DXR, CMPul-DXR conjugates bound through Gly-Gly-Phe-Gly and Gly-Phe-Gly-Gly spacers significantly suppressed the tumor growth, while CMPul-DXR conjugate bound through Gly-Gly-Gly-Gly showed less antitumor effect than DXR. CMPul-DXR conjugate without spacer showed no in vivo antitumor effect even at a dose equivalent to as much as 20 mg/kg of DXR.

  发现多柔比星（DXR）的氨基与羧甲基支链淀粉（CMPul）的羧基直接或通过包括甘-甘-苯丙-甘、甘-苯丙-甘-甘和甘-甘-甘-甘的四肽间隔物结合。这些偶联物的DXR含量为6.1-7.1%，羧甲基的取代度为每个糖单元0.6。这些偶联物在磷酸盐缓冲盐水（PBS，pH 7.4）中聚集，形成内部为疏水性DXR、外部为亲水性CMPul的胶束。通过高效液相色谱法测定了在大鼠肝脏溶酶体酶存在下，从这些偶联物中释放的DXR的量。药物释放速率因偶联物的不同而异。通过甘-甘-苯丙-甘连接的CMPul-DXR偶联物在24小时内释放了其35%的DXR。另一方面，没有间隔物的CMPul-DXR偶联物未释放出自由DXR。通过监测单次静脉注射后肿瘤重量，研究了每种偶联物对携带Walker 256肿瘤的大鼠的抗肿瘤效果。与DXR相比，通过甘-甘-苯丙-甘和甘-苯丙-甘-甘间隔物连接的CMPul-DXR偶联物显著抑制了肿瘤生长，而通过甘-甘-甘-甘连接的CMPul-DXR偶联物的抗肿瘤效果低于DXR。即使剂量相当于20 mg/kg的DXR，没有间隔物的CMPul-DXR偶联物也没有显示出体内抗肿瘤效果。
• New methods in peptide synthesis. Part III. Protection of carboxyl group
  作者：G. C. Stelakatos、A. Paganou、L. Zervas

  DOI：10.1039/j39660001191

  日期：——

  For the protection of the carboxyl group of amino-acids during peptide synthesis, the acid-labile diphenylmethyl ester group was used. N-Trityl-(i.e., triphenylmethyl), N-formyl-, or N-o-nitrophenylsulphenyl-amino-acid diphenylmethyl esters were converted by known methods into the corresponding ester hydrochlorides. The deblocking of the carboxyl group was accomplished either by the action of dilute

  为了在肽合成过程中保护氨基酸的羧基，使用酸不稳定的二苯基甲基酯基。Ñ三苯甲基（即，三苯基甲基），Ñ甲酰基，或ñ - ö -nitrophenylsulphenyl个氨基酸的二苯基甲基酯是由公知的方法转化成相应的盐酸盐酯。羧基的解封是通过氯化氢或溴化氢在硝基甲烷中的稀溶液的作用，通过三氟乙酸或通过催化氢解作用来完成的。
• Peptidoaminobenzophenones, a novel class of ring-opened derivatives of 1,4-benzodiazepines
  作者：Kentaro Hirai、Teruyuki Ishiba、Hirohiko Sugimoto、Kazuyuki Sasakura、Toshio Fujishita、Tatsuro Toyoda、Yuji Tsukinoki、Hirokuni Joyama、Hisao Hatakeyama、Katsumi Hirose

  DOI：10.1021/jm00181a013

  日期：1980.7

  the corresponding NH derivatives. Some compounds had very high activities in antipentylenetetrazole and antifighting tests in mice when orally administered. Very weak toxicity was also found in these compounds. Water solubility of the peptidoaminobenzophenones and their salts were tested. Possible in these compounds. Water solubility of the peptidoaminobenzophenones and their salts were tested. Possible

  已通过几种途径制备了一系列新的肽氨基二苯甲酮，并对其中枢神经系统活性进行了评估。讨论了系列中的结构-活动关系。通常，二肽基-N-甲基氨基二苯甲酮显示出比相应的NH衍生物更高的活性。口服时，某些化合物在抗戊烯四唑和小鼠抗战斗试验中具有很高的活性。在这些化合物中也发现非常弱的毒性。测试了肽氨基二苯甲酮及其盐的水溶性。这些化合物中可能存在。测试了肽氨基二苯甲酮及其盐的水溶性。还讨论了通过末端氨基酸的酶促裂解将肽氨基二苯甲酮进行体内转化，然后化学环化成1,4-苯并二氮杂ze的方法。
• A Novel Rapamycin-Polymer Conjugate Based on a New Poly(Ethylene Glycol) Multiblock Copolymer
  作者：Wanyi Tai、Zhijin Chen、Ashutosh Barve、Zhonghua Peng、Kun Cheng

  DOI：10.1007/s11095-013-1192-3

  日期：2014.3

  Rapamycin has demonstrated potent anti-tumor activity in preclinical and clinical studies. However, the clinical development of its formulations was hampered due to its poor solubility and undesirable distribution in vivo. Chemical modification of rapamycin presents an opportunity for overcoming the obstacles and improving its therapeutic index. The objective of this study is to develop a drug-polymer conjugate to increase the solubility and cellular uptake of rapamycin. We developed the rapamycin-polymer conjugate using a novel, linear, poly(ethylene glycol) (PEG) based multiblock copolymer. Cytotoxicity and cellular uptake of the rapamycin-polymer conjugate were evaluated in various cancer cells. The rapamycin-polymer conjugate provides enhanced solubility in water compared with free rapamycin and shows profound activity against a panel of human cancer cell lines. The rapamycin-polymer conjugate also presents high drug loading capacity (wt% ~ 26%) when GlyGlyGly is used as a linker. Cellular uptake of the conjugate was confirmed by confocal microscopic examination of PC-3 cells that were cultured in the presence of FITC-labled polymer (FITC-polymer). This study suggests that the rapamycin-polymer conjugate is a novel anti-cancer agent that may provide an attractive strategy for treatment of a wide variety of tumors.

  雷帕霉素在临床前和临床研究中显示了强大的抗肿瘤活性。然而，由于其溶解度差和体内分布不理想，其制剂的临床开发受到了阻碍。对雷帕霉素进行化学修饰为克服这些障碍并改善其治疗指标提供了机会。本研究的目的是开发一种药物-聚合物结合物，以增加雷帕霉素的溶解度和细胞摄取。我们使用一种新型的线性聚(乙烯醇)（PEG）基多嵌段共聚物开发了雷帕霉素-聚合物结合物。我们在多种癌细胞中评估了雷帕霉素-聚合物结合物的细胞毒性和细胞摄取。与游离雷帕霉素相比，雷帕霉素-聚合物结合物在水中的溶解度得到了增强，并对一系列人癌细胞系表现出显著的活性。当使用GlyGlyGly作为连接体时，雷帕霉素-聚合物结合物还具有较高的药物负载能力（重量百分比约为26%）。通过对在FITC标记聚合物（FITC-聚合物）存在下培养的PC-3细胞进行共聚焦显微镜检查，确认了结合物的细胞摄取。这项研究表明，雷帕霉素-聚合物结合物是一种新型抗癌剂，可能为治疗多种肿瘤提供一种有吸引力的策略。
• Synthesen zyklischer Polypeptide. c-Tetraglycyl und c-Hexaglycyl. Über aktivierte Ester VII
  作者：R. Schwyzer、B. Iselin、W. Rittel、P. Sieber

  DOI：10.1002/hlca.19560390331

  日期：——

  Naturally occurring cyclo-polypeptides may be subdivided into two groups, according t o whether the rings contain only peptide linkages or not. The adjectives homodetic and heterodetic are proposed to differentiate these two types of cyclo-polypeptides.

  根据环是否仅包含肽键，可以将天然存在的环多肽分为两类。提出形容词同质和异质的形容词来区分这两种类型的环多肽。