Z(OMe)-Ala-ONp | 23336-96-1

• 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: Z(OMe)-Ala-ONp
• 英文别名: (4-nitrophenyl) (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]propanoate
• CAS: 23336-96-1
• 化学式: C₁₈H₁₈N₂O₇
• 分子量: 374.35
• InChiKey: QKZOZOXWWRPSAP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 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)-Ala-ONp 在 N-甲基吗啉 、 1-羟基苯并三唑 、 溶剂黄146 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 Z(OMe)-Ala-Ile-Asp(OChp)-Asn-His-Arg(Mts)-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

文献信息

• Studies on peptides. CXXXIX Solution synthesis of a 42-residue peptide corresponding to the entire amino acid sequence of human glucose-dependent insulinotropic polypeptide (GIP).
  作者：NOBUTAKA FUJII、MITSUYA SAKURAI、KENICHI AKAJI、MOTOYOSHI NOMIZU、HARUAKI YAJIMA、KAZUHIKO MIZUTA、MITSURU AONO、MOTOYUKI MORIGA、KAZUTOMO INOUE、RYO HOSOTANI、TAKAYOSHI TOBE

  DOI：10.1248/cpb.34.2397

  日期：——

  Eight peptide fragments were prepared by known amide-forming reactions as building blocks for the solution synthesis of the dotetracontapeptide corresponding to the entire amino acid sequence of human intestinal GIP (gastric inhibitory polypeptide or glucose-dependent insulinotropic polypeptide). Besides Lys(Z), Trp(Mts) and Gln-OBzl, two new amino acid derivatives, Asp(OChp) and Glu(OChp) [Mts=mesitylenesulfonyl, Chp=cycloheptyl], were employed to suppress various side reactions. These fragments were successively assembled by the azide procedure to minimize racemization and all protecting groups employed were removed from the protected GIP by using 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.Synthetic GIP exhibited a significant glucose-dependent insulinotropic activity in dogs, but failed to produce any notable anti-gastric activity in rats.

  八个肽段通过已知的酰胺形成反应作为构建块，用于合成对应于人类肠道GIP（胃抑制多肽或葡萄糖依赖性胰岛素促进肽）完整氨基酸序列的四十肽。此外，除了Lys(Z)、Trp(Mts)和Gln-OBzl，还使用了两个新的氨基酸衍生物Asp(OChp)和Glu(OChp) [Mts=美克烯磺酰基，Chp=环庚基]，以抑制各种副反应。这些肽段通过叠氮化程序逐步组合，以最小化消旋化，所有使用的保护基团均通过在三氟乙酸中使用1M三氟甲烷磺酸-硫代苯醚去除。合成的GIP在犬中表现出显著的葡萄糖依赖性胰岛素促进活性，但未能在大鼠中产生任何显著的抗胃活性。
• 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。
• Studies on peptides. CVIII. Synthesis of the protected eicosapeptide corresponding to positions 19 to 38 of human parathyroid hormone.
  作者：SUSUMU FUNAKOSHI、HARUAKI YAJIMA

  DOI：10.1248/cpb.30.1697

  日期：——

  As a starting material for the synthesis of human parathyroid hormone (1-38), a C-terminal-protected eicosapeptide ester (positions 19-38) was synthesized by successive condensation of four peptide fragments; (positions 29-38), (25-28), (22-24) and (19-21).

  作为合成人甲状旁腺激素（1-38）的起始原料，通过连续缩合（29-38 位）、（25-28 位）、（22-24 位）和（19-21 位）四个肽段，合成了一个 C 端保护的二十肽酯（19-38 位）。
• Solution synthesis of a heptacosapeptide known as bovine .GAMMA.3-melanotropin (.GAMMA.3-MSH).
  作者：SHINICHI SHIMAMURA、KOICHI YASUMURA、KENJI OKAMOTO、KENJI MIYATA、AKIRA TANAKA、MASUHISA NAKAMURA、KENICHI AKAJI、HARUAKI YAJIMA

  DOI：10.1248/cpb.30.2433

  日期：——

  A heptacosapeptide (known as γ3-MSH) which is located within the amino acid sequence of bovine corticotropin-β-lipotropin precursor protein was synthesized by fragment condensation of Z-(1-12)-OSu and H-(13-27)-OBzl followed by deprotection with trifluoromethanesulfonic acid-thioanisole in TFA. The synthetic peptide exhibited weak melanocyte-stimulating activity (1.5×106 U/g, in vitro).

  通过 Z-(1-12)-OSu 和 H-(13-27)-OBzl 的片段缩合，然后在反式脂肪酸中用三氟甲磺酸-硫代苯甲醚进行脱保护，合成了位于牛促肾上腺皮质激素-β-促脂腺激素前体蛋白氨基酸序列内的七肽 （称为 γ3-MSH）。合成肽具有微弱的黑色素细胞刺激活性（体外 1.5×106 U/g）。
• Studies on peptides. CXVI. Synthesis of the protected docosapeptide corresponding to the C-terminal portion of human growth hormone releasing factor (GRF, somatocrinin).
  作者：NOBUTAKA FUJII、MASANORI SHIMOKURA、KENICHI AKAJI、SHINYA KIYAMA、HARUAKI YAJIMA

  DOI：10.1248/cpb.32.510

  日期：——

  As a starting material for the solution synthesis of a tetratetracontapeptide amide corresponding to the entire sequence of growth hormone releasing factor derived from human pancreatic tumor, a C-terminal-protected docosapeptide amide (positions 23-44) was synthesized by successive azide condensation of three peptide fragments (positions 33-44, 28-32, and 23-27). Amino acid derivatives bearing protecting groups removable by trifluoromethanesulfonic acid were employed; i.e., benzyloxycarbonyl (Z), benzyl (Bzl), and mesitylene-2-sulfonyl (Mts).

  作为溶液合成对应于从人类胰腺肿瘤中提取的生长激素释放因子整个序列的四重四肽酰胺的起始原料，通过连续缩合三个肽片段（位置 33-44、28-32 和 23-27）的叠氮化物，合成了一个 C 端受保护的二十二肽酰胺（位置 23-44）。采用的氨基酸衍生物含有可被三氟甲磺酸去除的保护基团，即苄氧羰基（Z）、苄基（Bzl）和介苯-2-磺酰基（Mts）。