Z(OMe)-Gly-OSu | 108304-82-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Z(OMe)-Gly-OSu
• 英文别名: (2,5-dioxopyrrolidin-1-yl) 2-[(4-methoxyphenyl)methoxycarbonylamino]acetate
• CAS: 108304-82-1
• 化学式: C₁₅H₁₆N₂O₇
• 分子量: 336.301
• InChiKey: JYGBPZFSRFPTJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  111.24
• 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-OSu 在 一水合肼 、 三乙胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Z(OMe)-Gly-Gln-Gly-NHNH2
  参考文献：
  名称：

  肽的研究。CXLV。合成27种残基的肽酰胺，其对应于犬胃泌素释放多肽（cGRP）的整个氨基酸序列。

  摘要：

  犬胃泌素释放多肽（cGRP，其特征为类似于蚕豆蛋白的 27 个残基的多肽）是通过连续缩合 7 个纯度已确定的多肽片段，然后在三氟乙酸中用三氟甲磺酸进行脱保护而合成的。在去保护层之前，先用苯基硫代三甲基硅烷在一定量的三氟甲磺酸三甲基硅酯催化下进行短暂处理，还原受保护 cGRP 中的 Met(O) 残基。经 HPLC 纯化的均相产物与合成的人 GRP 相似，能显著提高大鼠血浆中的免疫活性胃泌素水平。

  DOI：

  10.1248/cpb.34.4805

文献信息

• 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。
• Synthesis of an immunologically active fragment analog of prothymosin .ALPHA. with enhanced enzymatic stability.
  作者：Takashi ABIKO、Hiroshi SEKINO

  DOI：10.1248/cpb.39.752

  日期：——

  A fragment analog, [D-Arg30]prothymosin α fragment 1-30, containing D-arginine in place of arginine residue at position 30 was synthesized by the liquid phase procedure and studied for immunological effect on the impaired blastogenic response of T-lymphocytes isolated from uremic patients after treatment of human serum. Deacetyl-thymosin α1, a synthetic octaeicosapeptide corresponding to deacetyl-prothymosin α fragment 1-28, has restoration ability for the impaired blastogenic response of T-lymphocytes of uremic patients but is susceptible to proteolytic digestion. On the other hand, the fragment analog, [D-Arg30]prothymosin α fragment 1-30 retained activity and was shown to exhibit a high degree of stability when incubated in human serum. These results indicate that N-terminal acetylation and the introduction of D-residue into the C-terminal residue of prothymosin α fragment 1-30 increase resistance to proteolytic degradation by exopeptidases.

  通过液相法合成了一种片段类似物[D-Arg30]胸腺肽α片段1-30，该片段含有D-精氨酸，取代了第30位的精氨酸残基。脱乙酰胸腺肽α1是一种与脱乙酰胸腺肽α片段1-28相对应的合成八代肽，它对尿毒症患者T淋巴细胞受损的鼓泡生成反应具有恢复能力，但易被蛋白酶消化。另一方面，片段类似物[D-Arg30]原胸腺肽α片段 1-30 保留了活性，并且在人血清中培养时表现出高度稳定性。这些结果表明，原胸腺肽α片段1-30的N端乙酰化和在C端残基中引入D-残基可增强对外肽酶蛋白分解的抵抗力。
• Studies on peptides. CLXIV. Solution-phase synthesis of a 36-residue peptide amide corresponding to the entire amino acid sequence of chicken antral peptide.
  作者：LILI Guo、EIGORO MURAYAMA、SUSUMU FUNAKOSHI、NOBUTAKA FUJII、MITSURU AONO、MASAYUKI MATSUDA、MOTOYUKI MORIGA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.4364

  日期：——

  A 36-residue peptide amide corresponding to the entire amino acid sequence of chicken antral peptide was synthesized by assembling seven peptide fragments via the azide, followed by thioanisole-mediated deprotection with trimethylsilyl bromide and trimethylsilyl trifluoromethanesulfonate in trifluoroacetic acid.The synthetic peptide stimulated gastric secretion, but not pancreatic secretion.

  通过叠氮化物组装七个肽片段，然后在三氟乙酸中用三甲基溴硅烷和三氟甲磺酸三甲基硅烷酯介导的硫代茴香醚介导的去保护，合成了对应于鸡胃窦肽的整个氨基酸序列的36个残基的肽酰胺。合成的肽刺激胃液分泌，但不是胰腺分泌。
• Studies on peptides. CL. Syntheses of (D-His2)-analogs of enkephalin and adrenorphin and several (D-Arg2)enkephalin analogs.
  作者：SUSUMU FUNAKOSHI、MINORU KUBOTA、NAOTO KOSUGA、JIAN-PING XU、HARUAKI YAJIMA、WEI LI、SHIGEKI TAMURA、SHUJI KANEKO、MASAMICHI SATOH、HIROSHI TAKAGI

  DOI：10.1248/cpb.35.2561

  日期：——

  [D-His2] Leu-enkephalin and [D-His2] adrenorphin were synthesized. In addition, eight [D-Arg2] enkephalin-related peptides were synthesized. Their inhibitory effects on electrically stimulated myenteric plexus-longitudinal muscle preparations of guinea-pig ileum were examined.

  合成了[D-His2] Leu-脑啡肽和[D-His2] 肾上腺啡肽。此外，还合成了八种[D-Arg2]脑啡肽相关肽。研究了这些肽对电刺激豚鼠回肠肠肌丛纵肌制备物的抑制作用。
• Studies on peptides. CLIX. Preparation of a protected 33-residue peptide for the synthesis of human cholecystokinin (hCCK-33).
  作者：NOBUTAKA FUJII、SHIROH FUTAKI、SUSUMU FUNAKOSHI、KENICHI AKAJI、HIROSHI MORIMOTO、OSAMU IKEMURA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.3271

  日期：——

  A protected 33-residue peptide corresponding to the entire amino acid sequence of human cholecystokinin (hCCK-33) was synthesized by successive azide condensations of 7 peptide fragments of established purity. β-Cycloheptyl aspartate [Asp(OChp)] was employed to suppress base-catalyzed succinimide formation.

  通过连续叠氮化物缩合 7 个已确定纯度的肽片段，合成了对应于人胆囊收缩素 (hCCK-33) 完整氨基酸序列的受保护的 33 个残基肽。 β-环庚基天冬氨酸 [Asp(OChp)] 用于抑制碱催化的琥珀酰亚胺形成。