Z(OMe)-Gln-OH | 23234-81-3

• 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)-Gln-OH
• 英文别名: (2S)-5-amino-2-[(4-methoxyphenyl)methoxycarbonylamino]-5-oxopentanoic acid
• CAS: 23234-81-3
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: AXXNSSUZCRQLPH-NSHDSACASA-N

物化性质

• 熔点：
  143-144 °C(Solv: ethanol (64-17-5))
• 沸点：
  630.2±55.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  127.95
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z(OMe)-Gln-OH 在 钯 盐酸 、 氢气 、 1-羟基苯并三唑 、 一水合肼 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 Z(OMe)-Gln-Ser-Tyr-NHNH2
  参考文献：
  名称：

  牛胰腺核糖核酸酶A的全合成。第3部分。受保护的六戊烷肽肽酯（69-124位）的合成

  摘要：

  从与牛胰RNase A，Z（OMe）-（RNase 89-124）-OBzl序列相对应的被保护的六碳七肽开始，链延长到六五碳肽肽阶段，Z（OMe）-（RNase 69-124） ）-OBzl，通过肽片段Z（OMe）-Asp-（OBzl）-Cys（MBzl）-Arg（MBS）-Glu（OBzl）-Thr-Gly-NHNH-Troc的六次连续叠氮化物缩合，（10）， Z（OMe）-Ser-Ile-Thr-NHNH 2（11），Z（OMe）-Ser-Thr-Met（O）-NHNH 2（12），Z（OMe）-Gln-Ser-Tyr-NHNH 2（13），Z（OMe）-Asn-Cys（MBzl）-Tyr-NHNH 2（14），和Z（OMe）-Gln-Thr-NHNH 2（15）。在缩合之前，通过用Zn处理从片段（10）中除去Troc基团。与N-甲基吡咯烷酮-5％H 2O作为洗脱剂，在Sephacryl

  DOI：

  10.1039/p19810000804
• 作为产物：
  描述：

  2-(4-甲氧基苄氧基羰基氧基亚氨基)-2-苯乙腈 、 L-谷氨酰胺 以94%的产率得到
  参考文献：
  名称：

  CHEN, SHUI-TEIN;WENG, CHIH-SHYONG;WANG, KUNG-TSUNG, J. CHIN. CHEM. SOC., 34,(1987) N 2, 117-123

  摘要：

  DOI：

文献信息

• Amino Acids and Peptides. XVIII. Synthetic Peptides Related to N-Terminal Portion of Fibrin .ALPHA.-Chain and Their Inhibitory Effect on Fibrinogen/Thrombin Clotting.
  作者：Koichi KAWASAKI、Masanori MIYANO、Katsuhiko HIRASE、Masahiro IWAMOTO

  DOI：10.1248/cpb.41.975

  日期：——

  Peptide analogs of the N-terminal portion of fibrin α-chain were prepared and their inhibitory effects on fibrinogen/thrombin clotting were examined. Of the synthetic peptides, H-Gly-Pro-Arg-Pro-Pro-NH2 exhibited the most potent inhibitory effect.

  纤维α链N末端部分的肽类似物被制备出来，并考察了它们对纤维蛋白原/凝血酶凝固的抑制作用。在合成的肽中，H-Gly-Pro-Arg-Pro-Pro-NH₂表现出最强的抑制效果。
• Amino acids and peptides. VI. Synthesis of the N-terminal pentapeptide of .ALPHA.2-plasmin inhibitor and its analogue.
  作者：SATOSHI OKUSADA、KOICHI KAWASAKI、NOBUTOSHI SUGIYAMA

  DOI：10.1248/cpb.33.3484

  日期：——

  The N-terminal pentapeptide of α2-plasmin inhibitor, H-Asn-Gln-Glu-Gln-Val-OH, and its analogue, H-Asp-Gln-Glu-Gln-Val-OH, were synthesized and their inhibitory effects on the cross-linking reaction of α2-plasmin inhibitor to fibrin mediated by factor XIIIa were examined. The synthetic peptides were inhibitory at high concentration.

  α2-纤溶酶抑制剂的N端五肽H-Asn-Gln-Glu-Gln-Val-OH及其类似物H-Asp-Gln-Glu-Gln-Val-OH被合成，并对其在因子XIIIa介导的α2-纤溶酶抑制剂与纤维蛋白的交联反应中的抑制作用进行了研究。合成的肽在高浓度下具有抑制作用。
• 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。
• Amino Acids and Peptides. XVII. Synthesis of Peptides Related to N-Terminal Portion of Fibrin .ALPHA.-Chain and Their Inhibitory Effect on Fibrinogen/Thrombin Clotting.
  作者：Koichi KAWASAKI、Toshiki TSUJI、Katuhiko HIRASE、Masanori MIYANO、Sachiye INOUE、Masahiro IWAMOTO

  DOI：10.1248/cpb.41.525

  日期：——

  Various peptides related to N-terminal portion of fibrin alpha-chain were synthesized by the solution method and the solid-phase method, and their inhibitory effect on fibrinogen/thrombin clotting was examined. Extension of peptide chain from N-terminal tripeptide decreased the inhibitory effect. The most potent effect was shown by N-terminal decapeptide analog, H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2

  通过溶液法和固相法合成了与纤维蛋白α链的N末端部分有关的各种肽，并研究了它们对纤维蛋白原/凝血酶凝血的抑制作用。N端三肽的肽链延伸降低了抑制作用。N端十肽类似物H-Gly-Pro-Arg-Pro-Pro-Glu-Arg-His-Gln-Ser-NH2显示了最有效的作用。
• Studies on peptides. CXLVI Synthesis of Gln15-motilin and examination of its immunological properties.
  作者：SUZUMITSU KUNO、WEI LI、NOBUTAKA FUJII、HIDEKI ADACHI、KIYOSHI BESSYO、TOMIO SEGAWA、YOSHIHIRO NAKATA、ATSUKO INOUE、HARUAKI YAJIMA

  DOI：10.1248/cpb.34.4811

  日期：——

  Gln15-motilin was synthesized in a conventional manner by assembling seven peptide fragments followed by deprotection with 1M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The usefulness of phenylthiotrimethylsilane for the reduction of Met(O) was confirmed. This motilin analog was as biologically active as synthetic motilin in terms of contraction of rabbit duodenal muscles, but in radioimmunoassay it was only about 25% as reactive with antiserum raised against synthetic porcine motilin.

  Gln15-motilin通过传统方法合成，即组装七个肽片段，然后用1M三氟甲磺酸-三氟乙酸中的三氟甲磺酸-三氟乙酸进行脱保护。苯基硫代三甲基硅烷在还原Met（O）方面的有效性得到了证实。在兔十二指肠肌肉收缩方面，这种促胃肠蠕动素类似物与合成促胃肠蠕动素一样具有生物活性，但在放射免疫测定中，它与针对合成猪促胃肠蠕动素产生的抗血清的反应性只有约25%。