(S)-2-(4-Methoxy-benzyloxycarbonylamino)-pentanedioic acid 5-benzyl ester 1-(4-nitro-phenyl) ester | 53049-31-3

• 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: (S)-2-(4-Methoxy-benzyloxycarbonylamino)-pentanedioic acid 5-benzyl ester 1-(4-nitro-phenyl) ester
• 英文别名: Z(OMe)-Glu(OBzl)-ONp；5-O-benzyl 1-O-(4-nitrophenyl) (2S)-2-[(4-methoxyphenyl)methoxycarbonylamino]pentanedioate
• CAS: 53049-31-3
• 化学式: C₂₇H₂₆N₂O₉
• 分子量: 522.511
• InChiKey: SXPPUMBRUUQWIU-DEOSSOPVSA-N

物化性质

• 沸点：
  704.4±60.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  143.3
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-Methoxy-benzyloxycarbonylamino)-pentanedioic acid 5-benzyl ester 1-(4-nitro-phenyl) ester 在 ammonium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以72%的产率得到Z(OMe)-Glu(OBzl)-NH2
  参考文献：
  名称：

  Studies on peptides. CXX. Synthesis of growth hormone releasing factor (GRF-37-NH2) and N.ALPHA.-biotinyl-GRF-44-NH2.

  摘要：

  与人胰腺肿瘤衍生肽之一（称为生长激素释放因子（hpGRF））的完整氨基酸序列相对应的七十三肽的酰胺形式是使用苯硫基苯甲醚介导的脱保护程序以常规方式合成的。在体内测定中，该肽 (hpGRF-37-NH2) 与合成的四十四肽酰胺 (hpGRF-44-NH2) 具有相同的活性。然而，在体外测定中，合成的hpGRF-37-NH2的效力仅为合成的hpGRF-44-NH2的15%。此外，还制备了 Nα-生物素-GRF-44-NH2 用于组织化学受体研究。该 GRF 衍生物的活性约为 hpGRF-44-NH2 的 60%。

  DOI：

  10.1248/cpb.32.1200

文献信息

• Studies on peptides. CXXVI. Synthesis of the protected tetracosapeptide corresponding to positions 30-53 of mouse epidermal growth factor (EGF).
  作者：KENICHI AKAJI、NOBUTAKA FUJII、HARUAKI YAJIMA

  DOI：10.1248/cpb.33.173

  日期：——

  As a starting material for the synthesis of mouse epidermal growth factor, a half of the molecule, the protected tetracosapeptide ester (positions 30-53), was synthesized by successive condensations of eight peptide fragments : (positions 51-53), (49-50), (46-48), (42-45), (39-41), (37-38), (34-36), (30-33).

  作为合成小鼠表皮生长因子起始原料的半个分子，即30-53位点的受保护二十四肽酯，是通过八个肽片段（51-53位点，49-50位点，46-48位点，42-45位点，39-41位点，37-38位点，34-36位点，30-33位点）的连续缩合反应合成的。
• 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。
• Facile reduction of methionine sulfoxide with sulfur trioxide/iodide ion system.
  作者：Shiroh FUTAKI、Takeshi YAGAMI、Takashi TAIKE、Toyoko OGAWA、Tadashi AKITA、Kouki KITAGAWA

  DOI：10.1248/cpb.38.1165

  日期：——

  A new system for the facile reduction of Met(O) in protected peptides (dimethylformamide-sulfur trioxide complex/iodide ion) was introduced. Met(O) in protected Met-enkephalins and protected leucosulfakinins were reduced to Met within 1h by this system, and the reducing ability of this new system seemed comparable to or greater than that of the formerly reported dimethylformamide-sulfur trioxide complex/ethanedithiol system. The methylsulfinylbenzyl protecting group of Tyr was also reduced to a methylthiobenzyl group by this system.

  一种新系统被引入，用于在保护肽中便捷地还原Met(O)（二甲基甲酰胺-三氧化硫复合物/碘离子）。在此系统的作用下，保护的Met-恩凯法林和保护的白介素硫肽中的Met(O)在1小时内被还原为Met。这个新系统的还原能力似乎与以前报道的二甲基甲酰胺-三氧化硫复合物/乙烷二硫系统相当或更强。此外，Tyr的甲基亚磺酰苯基保护基也被该系统还原为甲基硫苯基基团。
• Synthesis of the untriacontapeptide corresponding to the entire amino acid sequence of human .BETA.-endorphin.
  作者：MINORU KUBOTA、TADAMASA HIRAYAMA、OSAMU NAGASE、HARUAKI YAJIMA

  DOI：10.1248/cpb.26.2139

  日期：——

  In a conventional manner, the untriacontapeptide corresponding to the entire amino acid sequence of human β-endorphin was synthesized using amino acid derivatives, Lys (Z) Glu (OBzl), bearing protecting groups removable by methanesulfonic acid. Potency ratios of the synthetic peptide to morphin (taken as 1) was 6.5, when assayed the analgesic effect on tail pinch method in mice.

  按照常规方法，合成了对应人β-内啡肽整个氨基酸序列的三十肽，使用了带有可由甲磺酸去除的保护基团的氨基酸衍生物Lys (Z) Glu (OBzl)。在小鼠尾夹法测定镇痛效果时，合成肽的效能与吗啡（视为1）的比值为6.5。
• 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。