Z(OMe)-Leu-ONP | 51165-15-2

• 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: Z(OMe)-Leu-ONP
• 英文别名: (4-nitrophenyl) (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]-4-methylpentanoate
• CAS: 51165-15-2
• 化学式: C₂₁H₂₄N₂O₇
• 分子量: 416.431
• InChiKey: ITYZUWPWPAVIBN-IBGZPJMESA-N

物化性质

• 沸点：
  590.5±50.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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)-Leu-ONP 在 一水合肼 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 {(S)-1-[(S)-1-((S)-1-Azidocarbonyl-ethylcarbamoyl)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid 4-methoxy-benzyl ester
  参考文献：
  名称：

  Studies on peptides. LXXXVI. Application of the trifluoroacetic acid-thioanisole deprotecting procedure for the synthesis of a wasp venom, mastoparan.

  摘要：

  一种新的去保护过程，采用三氟乙酸-硫代苯酚-m-甲酚去除赖氨酸N6氨基上的苄氧羰基。在此过程中合成了一种黄蜂毒素马斯托帕兰，以验证其在肽合成中的有效性。

  DOI：

  10.1248/cpb.28.1214

文献信息

• Studies on peptides. CXXVI. Synthesis of the protected tetracosapeptide corresponding to positions 30-53 of mouse epidermal growth factor (EGF).
  作者：KENICHI AKAJI、NOBUTAKA FUJII、HARUAKI YAJIMA

  DOI：10.1248/cpb.33.173

  日期：——

  As a starting material for the synthesis of mouse epidermal growth factor, a half of the molecule, the protected tetracosapeptide ester (positions 30-53), was synthesized by successive condensations of eight peptide fragments : (positions 51-53), (49-50), (46-48), (42-45), (39-41), (37-38), (34-36), (30-33).

  作为合成小鼠表皮生长因子起始原料的半个分子，即30-53位点的受保护二十四肽酯，是通过八个肽片段（51-53位点，49-50位点，46-48位点，42-45位点，39-41位点，37-38位点，34-36位点，30-33位点）的连续缩合反应合成的。
• Studies on peptides. CXL Synthesis of human gastrin-releasing polypeptide (hGRP).
  作者：SUZUMITSU KUNO、KENICHI AKAJI、OSAMU IKEMURA、MOTOYUKI MORIGA、MITSURU AONO、KAZUHIKO MIZUTA、ATSUSHI TAKAGI、HARUAKI YAJIMA

  DOI：10.1248/cpb.34.2462

  日期：——

  Human gastrin-releasing polypeptide (hGRP), which consists of 27 amino acid residues with a C-terminal amide, was synthesized by a conventional solution method, by assembling six peptide fragments followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. Met(O) employed was reduced by treatment with phenylthiotrimethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate before deprotection. The synthetic peptide was as active as synthetic porcine GRP, in terms of immunoreactive gastrin release in rats.

  人类促胃液释放多肽（hGRP）由27个氨基酸残基组成，具有C末端胺，采用常规溶液法合成，通过组装六个肽片段，并使用1M三氟甲烷磺酸-thioanisole在三氟乙酸中进行去保护。使用的Met(O)在去保护之前，通过在三甲基硅基三氟甲烷磺酸盐存在下，用苯硫基三甲基硅烷处理进行还原。合成的肽在大鼠的免疫反应性促胃液释放方面与合成的猪GRP具有相同的活性。
• Studies on peptides. CIX. Synthesis of the octatriacontapeptide corresponding to positions 1 to 38 of human parathyroid hormone.
  作者：SUSUMU FUNAKOSHI、NOBUTAKA FUJII、HARUAKI YAJIMA、CHOHEI SHIGENO、ITSUO YAMAMOTO、RIKUSHI MORITA、KANJI TORIZUKA

  DOI：10.1248/cpb.30.1706

  日期：——

  The octatriacontapeptide corresponding to positions 1 to 38 of human parathyroid hormone (hPTH), a half of the whole molecule, was synthesized by assembling 9 peptide fragments in a conventional manner. Arg (mesitylene-2-sulfonyl), a new arginine derivative bearing an acid-labile protecting group, was employed in combination with a new deprotecting procedure with 1 M trifluoromethanesulfonic acid-thioanisole in TFA. The synthetic peptide exhibited an activity of 1400 IU/mg when assayed by the mouse bone adenyl cyclase activity assay.

  合成人类甲状旁腺激素（hPTH）第1到第38位的八三十肽，通过传统方法组装9个肽片段合成。使用了一种新型的精氨酸衍生物Arg（美克辛烯-2-磺酸），该衍生物具有一种酸敏感的保护基团，并结合了使用1 M三氟甲烷磺酸-硫代苯醚在TFA中进行的新脱保护工艺。合成的肽在小鼠骨腺苷酸酰化酶活性测定中表现出1400 IU/mg的活性。
• Studies on peptides. CXXXIII. Synthesis and biological activity of galanin, a novel porcine intestinal polypeptide.
  作者：HARUAKI YAJIMA、SHIROH FUTAKI、NOBUTAKA FUJII、KENICHI AKAJI、SUSUMU FUNAKOSHI、MITSUYA SAKURAI、SHINICHI KATAKURA、KAZUTOMO INOUE、RYO HOSOTANI、TAKAYOSHI TOBE、TOMIO SEGAWA、ATSUKO INOUE、KAZUHIKO TAKEMOTO、VIKTOR MUTT

  DOI：10.1248/cpb.34.528

  日期：——

  A new porcine gastrointestinal 29-residue peptide, galanin, was synthesized in a satisfactory yield by assembling seven peptide fragments followed by deprotection with 1 M trifluoromethane-sulfonic acid-thioanisole in trifluoroacetic acid. Nin-Mesitylenesulfonyltryptophan was employed to suppress indole alkylation during Na-deprotection. β-Cycloheptylaspartate was employed to suppress base-catalyzed succinimide formation. The synthetic peptide exhibited a powerful contractile activity on rat ileum, but not on guinea pig ileum and caused sustained hyperglycemia in dogs.

  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。
• Studies on peptides. CXII. Alternative synthesis of heptacosapeptide, a new gastrointestinal polypeptide.
  作者：NOBUTAKA FUJII、WI LEE、HARUAKI YAJIMA、MOTOYUKI MORIGA、KAZUHIKO MIZUTA

  DOI：10.1248/cpb.31.3503

  日期：——

  A recently found gastrointestinal hormone, PHI (heptacosapeptide), was synthesized in a different manner from that of Moroder et al. [Z. Naturforsch., 37b, 772 (1982) ]. Our synthesis was carried out by successive azide condensation of six peptide fragments (23-27, 19-22, 15-18, 11-14, 7-10, and 1-6), followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The deprotected peptide was purified by gel-filtration on Sephadex G-25, followed by ion-exchange chromatography on CM-Biogel A and reverse phase high-performance liquid chromatography on μBondapak C18. The homogeneous product thus obtained produced a remarkable decrease in systemic blood pressure in anesthetized rats. In addition, Nα-biotinyl-PHI was synthesized for histochemical receptor-binding studies.

  最近发现的一种胃肠激素PHI（七十七肽）与Moroder等人合成的方式不同[Z. Naturforsch., 37b, 772 (1982)]。我们的合成是通过六个肽片段（23-27、19-22、15-18、11-14、7-10和1-6）的连续叠加聚合反应进行的，随后用1 M三氟甲烷磺酸-硫醚在三氟乙酸中去保护。去保护的肽通过Sephadex G-25进行凝胶过滤纯化，随后进行CM-Biogel A上的离子交换色谱以及μBondapak C18上的反相高效液相色谱。由此获得的均匀产品在麻醉大鼠中显著降低了全身血压。此外，合成了Nα-生物素化-PHI用于组织化学受体结合研究。