L-苏氨酸,N-[[(4-甲氧苯基)甲氧基]羰基]-,酰肼 | 16152-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: L-苏氨酸,N-[[(4-甲氧苯基)甲氧基]羰基]-,酰肼
• 英文名称: Z(OMe)-Thr-NHNH2
• 英文别名: (4-methoxyphenyl)methyl N-[(2S,3R)-1-hydrazinyl-3-hydroxy-1-oxobutan-2-yl]carbamate
• CAS: 16152-87-7
• 化学式: C₁₃H₁₉N₃O₅
• 分子量: 297.311
• InChiKey: YYZQRDGFEFOSHH-KCJUWKMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.34
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  122.91
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  L-苏氨酸,N-[[(4-甲氧苯基)甲氧基]羰基]-,酰肼 在 diazotizing reagent 、 一水合肼 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Z(OMe)-Thr-Arg(Mts)-Leu-NHNH2
  参考文献：
  名称：

  Studies on peptides. XCV. Alternative synthesis of porcine vasoactive intestinal polypeptide (VIP).

  摘要：

  猪血管活性肠肽(VIP)的合成采用了两种不同的脱保护程序。除了氢氟酸外，发现TFA-硫代茴香醚能裂解所用的所有保护基团，包括苄酯、甲砷酸和三甲基硅基，并抑制了一种新发现的副反应，即自由羧基的天冬氨酸残基在酸性催化下形成琥珀酰亚胺。在pH 6下静置时，与Ser-Asp相连的N端组氨酸残基有少量被释放。

  DOI：

  10.1248/cpb.28.1873
• 作为产物：
  描述：

  L-苏氨酸甲酯 、 4-甲氧基苄氧基羰酰叠氮物 生成 L-苏氨酸,N-[[(4-甲氧苯基)甲氧基]羰基]-,酰肼
  参考文献：
  名称：

  Ribonuclease T₁Peptides. I. Synthesis of a ProtectedN-Terminal Undecapeptide Containing Asparagine Residue in Third Position

  摘要：

  由对甲氧基苄氧羰基七肽酯与苏氨酰-S-苄基-天冬氨酰-甘氨酰-丝氨酰-天冬氨酰-S-苄基-天冬氨酰-酪氨酸酯偶联合成。通过解锁 XXI 并用亮氨酸氨肽酶消化游离出的后十肽，确定了受保护的后十肽（XXI）的光学均匀性。

  DOI：

  10.1246/bcsj.40.204

文献信息

• 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 a 37-residue peptide amide corresponding to the entire amino acid sequence of .ALPHA.-form of rat calcitonin gene-related peptide (.ALPHA.-rCGRP).
  作者：KENSHI ANDO、KOUKI KITAGAWA、SHINYA KIYAMA、TATSUHIKO KAWAMOTO、TADASHI AKITA、ITSUO YAMAMOTO、KANJI TORIZUKA

  DOI：10.1248/cpb.35.60

  日期：——

  The heptatriacontapeptide amide corresponding to the entire amino acid sequence of α-form of rat calcitonin gene-related peptide (α-rCGRP) was synthesized by the conventional solution method. All protecting groups employed were removed by treatment with 1 M trifluoromethanesulfonic acid-thioanisole-trifluoroacetic acid, and the deprotected peptide was subjected to airoxidation to form the intramolecular disulfide bond. After purification by gel-filtration on Sephadex G-50, followed by reversed-phase high performance liquid chromatography, a highly purified sample of synthetic α-rCGRP was obtained. In terms of suppression of bone 45Ca-release stimulated by synthetic human parathyroid hormone (1-34), synthetic α-rCGRP was as active as synthetic human CGRP.

  采用传统的溶液法合成了与大鼠降钙素基因相关肽（α-rCGRP）的整个氨基酸序列相对应的七胜肽酰胺。用 1 M 三氟甲磺酸-硫代苯甲醚-三氟乙酸去除所有保护基团，然后对去保护基团的肽进行氧化反应以形成分子内二硫键。经 Sephadex G-50 凝胶过滤纯化后，再经反相高效液相色谱纯化，就得到了高度纯化的合成 α-rCGRP 样品。在抑制合成人甲状旁腺激素（1-34）刺激的骨 45Ca 释放方面，合成 α-rCGRP 与合成人 CGRP 具有同样的活性。
• 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。