Z(OMe)-Asp(OChp)-OSu | 108056-94-6

• 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)-Asp(OChp)-OSu
• 英文别名: 4-O-cycloheptyl 1-O-(2,5-dioxopyrrolidin-1-yl) (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]butanedioate
• CAS: 108056-94-6
• 化学式: C₂₄H₃₀N₂O₉
• 分子量: 490.51
• InChiKey: GQRMUFQYJHTSHK-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  137.54
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Z(OMe)-Asp(OChp)-OSu 在 N-甲基吗啉 、 苯甲醚 、 三氟乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Studies on peptides. CLIX. Preparation of a protected 33-residue peptide for the synthesis of human cholecystokinin (hCCK-33).

  摘要：

  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。

  DOI：

  10.1248/cpb.36.3271
• 作为产物：
  描述：

  Z(OMe)-Asp(OChp)-OH*CHA 生成 Z(OMe)-Asp(OChp)-OSu
  参考文献：
  名称：

  Futaki, Shiroh; Taike, Takashi; Yagami, Takeshi, Journal of the Chemical Society. Perkin transactions I, 1990, p. 1739 - 1744

  摘要：

  DOI：

文献信息

• Studies on peptides. CLX. Synthesis of a 33-residue peptide corresponding to the entire amino acid sequence of human cholecystokinin (hCCK-33).
  作者：NOBUTAKA FUJII、SHIROH FUTAKI、SUSUMU FUNAKOSHI、KENICHI AKAJI、HIROSHI MORIMOTO、RYUICHIRO DOI、KAZUTOMO INOUE、MASAFUMI KOGIRE、SHOICHIRO SUMI、MITSUTOSHI YUN、TAKAYOSHI TOBE、MITSURU AONO、MASAYUKI MATSUDA、HIROAKI NARUSAWA、MOTOYUKI MORIGA、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.3281

  日期：——

  An unsulfated form of human cholecystokinin (hCCK-33) was synthesized by successive azide condensations of seven peptide fragments, followed by deprotection with 1 M trimethylsilyl trifluoromethanesulfonate/trifluoroacetic acid. The phenolic group of Tyr (position 27) was selectively sulfated with pyridine-SO3 complex, after reversible masking of other functional groups with hard base (F-)-labile protecting groups, i.e., the amino functions with 9-fluorenyl-methyloxycarbonyl group and the hydroxyl functions of 4 Ser residues with tert-butyldiphenylsilyl groups. In terms of pancreatic protein output and capillary blood flow in dogs, the relative potency of synthetic hCCK-33 with respect to that of synthetic CCK-8 (taken as 1 on a molar basis) was 0.9. In terms of gastric acid and pepsin output in rat in vivo assays, synthetic hCCK-33 was about 2- to 3-fold more potent than CCK-8 on a molar basis.

  一种人胆囊收缩素（hCCK-33）的非硫酸化形式通过七个肽片段的连续叠氮化缩合合成，随后用1 M三甲基硅烷三氟甲磺酸盐/三氟乙酸去保护。Tyr（位置27）的酚羟基在用具有硬碱性（F-）的保护基团可逆掩蔽其他功能基团后，选择性地与吡啶-SO3复合物进行硫酸化，即用9-氟烯基-甲氧基羧基基团保护氨基功能，以及用叔丁基二苯基硅基团保护4个丝氨酸残基的羟基功能。在犬的胰腺蛋白输出和毛细血管血流方面，合成的hCCK-33相对于合成的CCK-8（以1为摩尔基准）的相对效力为0.9。在大鼠体内实验中，合成的hCCK-33在胃酸和胃蛋白酶的输出方面，其效力比CCK-8高约2到3倍。
• 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. 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. CLXIII. Synthesis of guinea pig vasoactive intestinal polypeptide (gVIP).
  作者：MIKA HATANO、SUSUMU FUNAKOSHI、NOBUTAKA FUJII、MASAHARU TAKEYAMA、MITSUTOSHI YUN、KAZUTOMO INOUE、MASAFUMI KOGIRE、TAKAYOSHI TOBE、HARUAKI YAJIMA

  DOI：10.1248/cpb.36.3857

  日期：——

  A 28-residue peptide corresponding to the entire amino acid sequence of vasoactive intestinal polypeptide of guinea pig origin (gVIP) was synthesized by assembling 6 peptide fragments, followed by thioanisole-mediated deprotection with 1 M trimethylsilyl trifluoromethanesulfonate in trifluoroacetic acid. The synthetic peptide was biologically as active as synthetic porcine VIP, but behaved immunologically in a different manner from the above mammalian VIP.

  通过组装 6 个肽段，然后在三氟乙酸中用 1 M 三甲基硅基三氟甲磺酸酯进行硫代苯甲醚介导的脱保护，合成了与豚鼠源血管活性肠多肽（gVIP）整个氨基酸序列相对应的 28 位氨基酸肽。合成肽的生物活性与合成猪 VIP 相同，但免疫学行为与上述哺乳动物 VIP 不同。
• Studies on peptides. CLIII. Application of the hard-acid deprotecting procedure to the synthesis of ovine corticotropin releasing factor (oCRF).
  作者：KENICHI AKAJI、MOTOYOSHI NOMIZU、KAZUHIDE WATANABE、SUSUMU FUNAKOSHI、HIROO IMURA、TOSHIHIKO TSUKADA、JUNICHI FUKATA、HIROMICHI NAKAMUTA、MASAO KOIDA、NOBUTAKA FUJII、HARUAKI YAJIMA

  DOI：10.1248/cpb.35.3859

  日期：——

  A 41-residue peptide corresponding to the entire amino acid sequence of ovine corticotropin releasing factor (oCRF) was synthesized by assembling ten peptide fragments of established purity, followed by hard-acid deprotection with 1 M trimethylsilyl trifluoromethanesulfonate in trifluoroacetic acid. β-Cycloheptylaspartate was employed to minimize base-catalyzed succinimide formation. When tested by in vivo assay, synthetic oCRF was as active as synthetic hCRF in terms of ability to release immunoreactive corticotropin.

  通过组装十个已确定纯度的肽片段，然后用三氟乙酸中的 1 M 三甲基甲硅烷基三氟甲磺酸酯进行硬酸脱保护，合成了对应于绵羊促肾上腺皮质激素释放因子 (oCRF) 整个氨基酸序列的 41 个残基肽。 β-环庚基天冬氨酸用于最大限度地减少碱催化的琥珀酰亚胺的形成。当通过体内测定进行测试时，合成的 oCRF 在释放免疫反应性促肾上腺皮质激素的能力方面与合成的 hCRF 一样活跃。