Z(OMe)-Gln-Gly-OMe | 67413-10-9

• 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)-Gln-Gly-OMe
• 英文别名: methyl 2-[[(2S)-5-amino-2-[(4-methoxyphenyl)methoxycarbonylamino]-5-oxopentanoyl]amino]acetate
• CAS: 67413-10-9
• 化学式: C₁₇H₂₃N₃O₇
• 分子量: 381.386
• InChiKey: KHLFXDXCAIINDO-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.16
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  146.05
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Z(OMe)-Gln-Gly-OMe 在 盐酸 、 苯甲醚 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 Z(OMe)-Arg(Mts)-Gln-Gln-Gly-OMe
  参考文献：
  名称：

  Studies on peptides. CXVI. Synthesis of the protected docosapeptide corresponding to the C-terminal portion of human growth hormone releasing factor (GRF, somatocrinin).

  摘要：

  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）。

  DOI：

  10.1248/cpb.32.510

文献信息

• 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.
  作者：NOBUTAKA FUJII、OSAMU IKEMURA、SUSUMU FUNAKOSHI、HISAYUKI MATSUO、TOMIO SEGAWA、YOSHIHIRO NAKATA、ATSUKO INOUE、HARUAKI YAJIMA

  DOI：10.1248/cpb.35.1076

  日期：——

  The usefulness of a new deprotecting procedure was demonstrated in the solution syntheses of two porcine spinal cord peptides, designated neuromedin U-8 and neuromedin U-25. Protected neuromedin U-8 (8-residue peptide), prepared by condensation of two fragments, served as a C-terminal amino component for the synthesis of neuromedin U-25 (25-residue peptide). Onto this fragment, five peptide fragments were successively condensed by the azide procedure to construct the entire amino acid sequence of neuromedin U-25, a possible biosynthetic precursor of neuromedin U-8. All protecting groups were cleaved from protected neuromedin U-8 and neuromedin U-25 by 1 M trimethylsilyl trifluoromethanesulfonate-thioanisole in trifluoroacetic acid. The results were compared with those obtained by trifluoromethanesulfonic acid deprotection. In terms of contractile activity in rat uterus, neuromedin U-25 was twice as active as neuromedin U-8.

  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。
• 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. CXLV Synthesis of a 27-residue peptide amide corresponding to the entire amino acid sequence of canine gastrin-releasing polypeptide (cGRP).
  作者：SUZUMITSU KUNO、KENICHI AKAJI、MITSURU AONO、ATSUSHI TAKAGI、MOTOYUKI MORIGA、KIYOSHI BESSYO、HARUAKI YAJIMA

  DOI：10.1248/cpb.34.4805

  日期：——

  Canine gastrin-releasing polypeptide (cGRP, characterized as a bombesin-like 27-residue peptide) was synthesized by successive azide condensations of 7 peptide fragments of established purity, followed by deprotection with trifluoromethanesulfonic acid in trifluoroacetic acid. Prior to deprotection, the Met(O) residue in the protected cGRP was reduced by brief treatment with phenylthiotrimethylsilane in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate. The homogeneous HPLC-purified product induced a significant increase of immunoreactive gastrin level in rat plasma, like synthetic human GRP.

  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。
• GUO, LILI;MURAYAMA, EIGORO;FUNAKOSHI, SUSUMU;FUJII, NOBUTAKA;AONO, MITSUR+, CHEM. AND PHARM. BULL., 36,(1988) N1, C. 4364-4376
  作者：GUO, LILI、MURAYAMA, EIGORO、FUNAKOSHI, SUSUMU、FUJII, NOBUTAKA、AONO, MITSUR+

  DOI：——

  日期：——