Z-(OMe)-Gly-ONp | 51165-13-0

• 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: Z-(OMe)-Gly-ONp
• 英文别名: Z(OMe)-Gly-ONp；(4-nitrophenyl) 2-[(4-methoxyphenyl)methoxycarbonylamino]acetate
• CAS: 51165-13-0
• 化学式: C₁₇H₁₆N₂O₇
• 分子量: 360.323
• InChiKey: LTKZXKZWFKVYOR-UHFFFAOYSA-N

物化性质

• 沸点：
  572.2±50.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117.0
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Z-(OMe)-Gly-ONp 在 一水合肼 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Z(OMe)-Gly-Pro-His-NHNH₂
  参考文献：
  名称：

  肽的研究。CXXXIII。新型猪肠多肽甘丙肽的合成及其生物学活性。

  摘要：

  一种新的猪胃肠道29残基肽——加拉宁，通过组合七个肽片段合成，并在三氟醋酸中使用1 M三氟甲烷磺酸-硫代苯醚进行去保护，获得了令人满意的产率。在钠去保护过程中，采用了九甲苯磺酰色氨酸以抑制吲哚烷基化。使用β-环庚基天冬氨酸来抑制碱催化的琥珀酰亚胺形成。合成的肽在大鼠回肠上表现出强有力的收缩活性，但在豚鼠回肠上没有影响，并且在狗身上引起持续性高血糖。

  DOI：

  10.1248/cpb.34.528
• 作为产物：
  描述：

  对硝基苯酚 、 N-{[(4-甲氧基苄基)氧基]羰基}甘氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 以66%的产率得到Z-(OMe)-Gly-ONp
  参考文献：
  名称：

  Amino Acids and Peptides. XXV. Preparation of Fibronectin-Related Peptide Poly(ethylene glycol) Hybrids and Their Inhibitory Effect on Experimental Metastasis.

  摘要：

  将整合素连接肽[精-甘-天冬 (RGD)，精-甘-天冬-丝 (RGDS)] 与聚乙二醇 (PEG) 的缀合物制备出来，并研究了它们对小鼠实验性转移的抑制作用。与聚乙二醇 #6000 形成的缀合物显著增强了 RGD 的抑制效果。在抑制作用方面，RGD 比 RGDS 更强，而 RGD PEG 缀合物优于 RGDS PEG 缀合物。与 PEG #4000 相比，与 PEG #6000 形成的缀合物效果更佳。

  DOI：

  10.1248/cpb.43.2133

文献信息

• Preparation of (Mrg-Gly-Asp)-(amino-poly(ethylene glycol)) hybrids and their inhibitory effect on experimental metastasis.
  作者：Koichi KAWASAKI、Machiko NAMIKAWA、Yuko YAMASHIRO、Takao HAMA、Tadanori MAYUMI

  DOI：10.1248/cpb.39.3373

  日期：——

  Hybrids of a fibronectin-related tripeptide (Arg-Gly-Asp) and amino-poly(ethylene glycol) were prepared and their inhibitory effect on experimental metastasis in mice was examined. The hybrids exhibited a potent inhibitory effect on the metastasis of B16 melanoma BL6.

  一种与纤连蛋白相关三肽（精氨酸-甘氨酸-天冬氨酸）和氨基聚乙二醇的混合物被制备出来，并考察了它们对小鼠实验性转移的抑制作用。这些混合物对B16黑色素瘤BL6的转移表现出强大的抑制效果。
• Synthesis of canine motilin, a gastric motor activity-stimulating polypeptide, and its N1-substituted analogs.
  作者：KOUKI KITAGAWA、KUNIO YONETO、SHINYA KIYAMA、KENSHI ANDO、TATSUHIKO KAWAMOTO、TADASHI AKITA、ATSUKO INOUE、TOMIO SEGAWA

  DOI：10.1248/cpb.33.3307

  日期：——

  The docosapeptide corresponding to the entire amino acid sequence of canine motilin, a newly characterized gastric motor activity-stimulating polypeptide, was synthesized by the conventional solution method. All protecting groups employed were removed by 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid and the deprotected peptide was purified by gel-filtration on Sephadex G-25, followed by partition chromatography and reverse phase high performance liquid chromatography. When contractile activity on rabbit duodenal muscle was examined, synthetic canine motilin was as active as synthetic porcine motilin. The relative potencies of Lys1 and Ser1 derivatives prepared in the same manner as canine motilin were ca. 1/1000 and 1/250, respectively.

  合成了与犬动脉肽（犬motilin）完整氨基酸序列对应的多肽，这是一种新特征的刺激胃肠运动活性的多肽，使用传统的溶液法合成。所有使用的保护基团均通过1 M三氟甲烷磺酸-硫醚-三氟乙酸去除，去保护的多肽通过Sephadex G-25的凝胶过滤进行纯化，随后进行分配色谱和反相高效液相色谱。在对兔十二指肠肌肉的收缩活性进行检验时，合成的犬动脉肽活性与合成的猪动脉肽相当。以与犬动脉肽相同的方法制备的赖氨酸1和丝氨酸1衍生物的相对效能分别约为1/1000和1/250。
• Enkephalin analogs containing the dipeptide unit Tyr-Arg (kyotorphin).
  作者：MINORU KUBOTA、OSAMU NAGASE、HIRO AMANO、HIROSHI TAKAGI、HARUAKI YAJIMA

  DOI：10.1248/cpb.28.2580

  日期：——

  Eight Met- and Leu-enkephalin analogs substituted with L- or D-Arg at position 2 were synthesized using NG-mesitylene-2-sulfonylarginine. Among them, H-Tyr-D-Arg-Gly-Phe-Met-OH was found to possess an analgesic effect 2.4 times higher than that of morphine on a molar basis, when injected intracisternally. This compound was also found to produce analgesia when administered intravenously.

  合成了八个在第2位分别用L-或D-精氨酸取代的甲硫脑啡肽和亮脑啡肽类似物，所用原料为NG-间甲苯-2-磺酰精氨酸。在鞘内注射时，发现其中的H-Tyr-D-Arg-Gly-Phe-Met-OH具有比吗啡高2.4倍的镇痛作用（摩尔比）。该化合物经静脉给药时也能产生镇痛作用。
• Studies on peptides. CXXXV. Preparation of seven peptide fragments for the synthesis of human calcitonin gene-related peptide (hCGRP).
  作者：NOBUTAKA FUJII、AKIRA OTAKA、SUSUMU FUNAKOSHI、MOTOYOSHI NOMIZU、KENICHI AKAJI、HARUAKI YAJIMA、KOUKI KITAGAWA、TADASHI AKITA、KENSHI ANDO、TATSUHIKO KAWAMOTO

  DOI：10.1248/cpb.34.603

  日期：——

  Seven peptide fragments were synthesized by known amide-forming reactions as building blocks for the solution-phase synthesis of the heptatriacontapeptide amide corresponding to the entire amino acid sequence of human calcitonin gene-related peptide (hCGRP). S-1-Adamantyl-cysteine [O. Nishimura, C. Kitada, and M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)] was employed, together with amino acid derivatives bearing protecting groups removable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.

  七个肽片段通过已知的酰胺形成反应合成，作为溶液相合成与人类降钙素基因相关肽（hCGRP）完整氨基酸序列相对应的七十氨基肽酰胺的构建块。采用了S-1-亚当烷基半胱氨酸 [O. Nishimura, C. Kitada, 和 M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)]，同时使用了具有保护基团的氨基酸衍生物，这些保护基团可通过1 M三氟甲磺酸-硫醇醚在三氟乙酸中去除。
• Synthesis of a 37-residue peptide amide corresponding to the entire amino acid sequence of .ALPHA.-form of rat calcitonin gene-related peptide (.ALPHA.-rCGRP).
  作者：KENSHI ANDO、KOUKI KITAGAWA、SHINYA KIYAMA、TATSUHIKO KAWAMOTO、TADASHI AKITA、ITSUO YAMAMOTO、KANJI TORIZUKA

  DOI：10.1248/cpb.35.60

  日期：——

  The heptatriacontapeptide amide corresponding to the entire amino acid sequence of α-form of rat calcitonin gene-related peptide (α-rCGRP) was synthesized by the conventional solution method. All protecting groups employed were removed by treatment with 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid, and the deprotected peptide was subjected to airoxidation to form the intramolecular disulfide bond. After purification by gel-filtration on Sephadex G-50, followed by reversed-phase high performance liquid chromatography, a highly purified sample of synthetic α-rCGRP was obtained. In terms of suppression of bone 45Ca-release stimulated by synthetic human parathyroid hormone (1-34), synthetic α-rCGRP was as active as synthetic human CGRP.

  采用传统的溶液法合成了与大鼠降钙素基因相关肽（α-rCGRP）的整个氨基酸序列相对应的七胜肽酰胺。用 1 M 三氟甲磺酸-硫代苯甲醚-三氟乙酸去除所有保护基团，然后对去保护基团的肽进行氧化反应以形成分子内二硫键。经 Sephadex G-50 凝胶过滤纯化后，再经反相高效液相色谱纯化，就得到了高度纯化的合成 α-rCGRP 样品。在抑制合成人甲状旁腺激素（1-34）刺激的骨 45Ca 释放方面，合成 α-rCGRP 与合成人 CGRP 具有同样的活性。