luteinizing hormone-releasing hormone | 47924-54-9

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: luteinizing hormone-releasing hormone
• 英文别名: Glu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2；(4S)-4-amino-5-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 47924-54-9
• 化学式: C₅₅H₇₇N₁₇O₁₄
• 分子量: 1200.32
• InChiKey: KTVPQHFLYINKPT-LVHVEONVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  86
• 可旋转键数：
  34
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  509
• 氢给体数：
  17
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  Nα-t-Butoxycarbonyl-L-(γ-tert-butoxy)glutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide Sesquiacetate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以0.0271 g的产率得到luteinizing hormone-releasing hormone
  参考文献：
  名称：

  Masiukiewicz, Elzbieta; Rzeszotarska, Barbara; Fortuna, Gabriela, Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 4, p. 573 - 578

  摘要：

  DOI：

文献信息

• Hydrolytic Cleavage of Pyroglutamyl-peptide Bond. V. Selective Removal of Pyroglutamic Acid from Biologically Active Pyroglutamylpeptides in High Concentrations of Aqueous Methanesulfonic Acid
  作者：Junko Kobayashi、Kazuhiro Ohki、Keiko Okimura、Tadashi Hashimoto、Naoki Sakura

  DOI：10.1248/cpb.54.827

  日期：——

  Application of aqueous methanesulfonic acid (MSA) for selective chemical removal of pyroglutamic acid (pGlu) residue from five biologically active pyroglutamyl-peptides (pGlu-X-peptides, X=amino acid residue at position 2) was examined. Gonadotropin releasing hormone (Gn-RH), dog neuromedin U-8 (d-NMU-8), physalaemin (PH), a bradykinin potentiating peptide (BPP-5a) and neurotensin (NT) as pGlu-X-peptides were incubated in either 70% or 90% aqueous MSA at 25 °C. HPLC analysis of the incubation solutions showed that the main decomposition product was H-X-peptide derived from each pGlu-X-peptide by the removal of pGlu. The results revealed that the pGlu-X peptide bond had higher susceptibility than various internal amide bonds in the five peptides examined, including the Trp-Ser bond in Gn-RH, the C-terminal Asn-NH2 in d-NMU-8, and the Asp-Pro bond in PH, whose acid susceptibility is well known. Thus, mild hydrolysis with high concentrations of aqueous MSA may be applicable to chemically selective removal of pGlu from pGlu-X-peptides for structural examinations.

  使用水溶性甲磺酸（MSA）选择性化学去除五种生物活性脯氨酸肽（pGlu-X-肽，X为位置2的氨基酸残基）中的脯氨酸残基的应用进行了研究。促性腺激素释放激素（Gn-RH）、犬神经肽U-8（d-NMU-8）、物理肽（PH）、一种缓激肽增效肽（BPP-5a）和神经肽（NT）作为pGlu-X肽，在25°C下分别在70%或90%的水溶性MSA中进行孵育。孵育溶液的HPLC分析显示，主要的分解产物是由每个pGlu-X肽去除pGlu后产生的H-X肽。结果表明，pGlu-X肽的肽键对酸的敏感性高于所研究的五种肽中的各种内酰胺键，包括Gn-RH中的色氨酸-丝氨酸键、d-NMU-8中的C末端天冬酰胺-NH2键，以及PH中的天冬氨酸-脯氨酸键，其酸敏感性是众所周知的。因此，使用高浓度水溶性MSA的温和水解可能适用于化学选择性去除pGlu，以便进行结构研究。
• Synthesis of LH-RH using a new phenolic polymer as solid support and “BOP” reagent for fragment coupling
  作者：P. Rivaille、J.P. Gautron、B. Castro、G. Milhaud

  DOI：10.1016/0040-4020(80)80193-1

  日期：1980.1

  p-Hydroxyphenyl propionic resin (Table I, compound 4) was used to prepare the 1–6 protected fragment of LH-RH which was then condensed with “BOP” (benzotriazolyl N-oxytrisdimethylaminophosphonium hexafluorophosphate) as coupling reagent to the 7–10 residue synthesized on the same resin. Peptidylresin was divided into two aliquots in order to obtain LH-RH after aminolysis and treatment with liquid hydrogen

  使用对羟基苯丙酸丙酯（表I，化合物4）制备LH-RH的1-6保护片段，然后与“ BOP”（苯并三唑N-氧基三二甲基氨基phosph六氟磷酸酯）缩合作为7-10残基的偶联剂在同一树脂上合成。肽基树脂分为两等份，以便在氨解和液氟化氢处理后得到LH-RH，在皂化后加氢或液化氟化氢处理后得到LH-RH-COOH。仅通过两次凝胶过滤就可以快速纯化得到的激素。
• Raap, J.; Kerling, K. E. T., Recueil des Travaux Chimiques des Pays-Bas, 1981, vol. 100, # 2, p. 62 - 64
  作者：Raap, J.、Kerling, K. E. T.

  DOI：——

  日期：——
• Iyer; Upadhye; Mahale, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 2, p. 233 - 236
  作者：Iyer、Upadhye、Mahale

  DOI：——

  日期：——
• Masiukiewicz, Elzbieta; Rzeszotarska, Barbara; Fortuna, Gabriela, Journal fur praktische Chemie (Leipzig 1954), 1991, vol. 333, # 4, p. 573 - 578
  作者：Masiukiewicz, Elzbieta、Rzeszotarska, Barbara、Fortuna, Gabriela、Kochman, Kazimierz

  DOI：——

  日期：——