Z(OMe)-Val-OSu | 23235-00-9

• 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)-Val-OSu
• 英文别名: Z(OMe)-Val-Su
• CAS: 23235-00-9
• 化学式: C₁₈H₂₂N₂O₇
• 分子量: 378.382
• InChiKey: JQIYYVYQOANUMU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 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：
  0.44
• 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)-Val-OSu 在 TEA 、 苯甲醚 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[2-((S)-2-Amino-3-methyl-butyrylamino)-acetylamino]-6-benzyloxycarbonylamino-hexanoic acid methyl ester
  参考文献：
  名称：

  Studies on peptides. CLXII. Synthesis of chicken calcitonin-gene-related peptide(cCGRP) by application of sulfoxide-directed disulfide-bond-forming reaction.

  摘要：

  通过叠氮化物连续组装七个肽片段，然后分两步对受保护的 cCGRP 进行酸处理，合成了对应于鸡降钙素基因相关肽 (cCGRP) 整个氨基酸序列的 37 个残基肽，即：在二苯硫醚存在下与三氟乙酸 (TFA) 反应，在 Cys(MBzl) 亚砜和 Cys(MBzl) 残基（分别为位置 2 和 7）之间建立二硫键，然后与 TFA 中的 1 M 三甲基甲硅烷基三氟甲磺酸酯反应以除去使用其余的保护基团。合成肽抑制小鼠颅盖释放 45Ca。

  DOI：

  10.1248/cpb.36.3304
• 作为产物：
  描述：

  (2S)-2-[(4-甲氧基苯基)甲氧基羰基氨基]-3-甲基丁酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 Z(OMe)-Val-OSu
  参考文献：
  名称：

  Studies on peptides. CXLVIII Application of a new deprotecting procedure with trimethylsilyl trifluoromethanesulfonate for the syntheses of two porcine spinal cord peptides, neuromedin U-8 and neuromedin U-25.

  摘要：

  在溶液合成两种猪脊髓多肽（分别为神经生长因子 U-8 和神经生长因子 U-25）的过程中，证明了新的去保护程序的实用性。通过缩合两个片段制备的受保护神经生长素 U-8（8 个残基的多肽）可作为合成神经生长素 U-25（25 个残基的多肽）的 C 端氨基成分。在这一片段上，用叠氮程序连续缩合了五个肽片段，从而构建了神经生长素 U-25 的整个氨基酸序列，它可能是神经生长素 U-8 的生物合成前体。在三氟乙酸中用 1 M 三甲基硅基三氟甲磺酸-硫代苯甲醚裂解了受保护的神经生长素 U-8 和神经生长素 U-25 上的所有保护基团。结果与三氟甲磺酸脱保护法的结果进行了比较。在大鼠子宫收缩活性方面，神经生长素 U-25 是神经生长素 U-8 的两倍。

  DOI：

  10.1248/cpb.35.1076

文献信息

• Studies on peptides. CXXVII. Synthesis of a tripentacontapeptide with epidermal growth factor activity.
  作者：KENICHI AKAJI、NOBUTAKA FUJII、HARUAKI YAJIMA、KYOZO HAYASHI、KAZUHIKO MIZUTA、MITSURU AONO、MOTOYUKI MORIGA

  DOI：10.1248/cpb.33.184

  日期：——

  The tripentacontapeptide corresponding to the entire linear sequence of epidermal growth factor was synthesized by assembling 15 peptide fragments and one His residue (position 22), followed by deprotection with trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The deprotected peptide was subjected to air-oxidation. After purification by ion-exchange chromatography on diethyl aminoethyl cellulose followed by high performance liquid chromatography, a peptide with powerful anti-gastric activity was obtained.

  通过组装15个肽片段和一个组氨酸残基（位置22），合成了对应于表皮生长因子整个线性序列的三十五肽。随后，通过三氟甲磺酸-噻吩在三氟乙酸中进行脱保护。脱保护的肽进行空气氧化。经过二乙氨基乙基纤维素上的离子交换色谱法纯化，接着用高效液谱法，获得了一种具有强大抗胃活性的肽。
• Studies on peptides. CXXXV. Preparation of seven peptide fragments for the synthesis of human calcitonin gene-related peptide (hCGRP).
  作者：NOBUTAKA FUJII、AKIRA OTAKA、SUSUMU FUNAKOSHI、MOTOYOSHI NOMIZU、KENICHI AKAJI、HARUAKI YAJIMA、KOUKI KITAGAWA、TADASHI AKITA、KENSHI ANDO、TATSUHIKO KAWAMOTO

  DOI：10.1248/cpb.34.603

  日期：——

  Seven peptide fragments were synthesized by known amide-forming reactions as building blocks for the solution-phase synthesis of the heptatriacontapeptide amide corresponding to the entire amino acid sequence of human calcitonin gene-related peptide (hCGRP). S-1-Adamantyl-cysteine [O. Nishimura, C. Kitada, and M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)] was employed, together with amino acid derivatives bearing protecting groups removable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid.

  七个肽片段通过已知的酰胺形成反应合成，作为溶液相合成与人类降钙素基因相关肽（hCGRP）完整氨基酸序列相对应的七十氨基肽酰胺的构建块。采用了S-1-亚当烷基半胱氨酸 [O. Nishimura, C. Kitada, 和 M. Fujino, Chem. Pharm. Bull., 26, 1576 (1978)]，同时使用了具有保护基团的氨基酸衍生物，这些保护基团可通过1 M三氟甲磺酸-硫醇醚在三氟乙酸中去除。
• 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。