胸腺五肽醋酸盐 | 85471-58-5

• 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
• 中文名称: 胸腺五肽醋酸盐
• 中文别名: 醋酸胸腺肽
• 英文名称: H-L-Arg-L-Lys-L-Asp-L-Val-L-Tyr-OH*3HOAc
• 英文别名: thymopentin triacetate；thymopentine；Thymopentin monoacetate；acetic acid;(3S)-3-[[(2S)-6-amino-2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]hexanoyl]amino]-4-[[(2S)-1-[[(1S)-1-carboxy-2-(4-hydroxyphenyl)ethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-oxobutanoic acid
• CAS: 85471-58-5；89318-88-7
• 化学式: 3C₂H₄O₂*C₃₀H₄₉N₉O₉
• 分子量: 859.932
• InChiKey: YRTISBKUCLDRGF-ADVSENJOSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  -2.31
• 重原子数：
  52
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  365
• 氢给体数：
  12
• 氢受体数：
  14

制备方法与用途

生物活性

Thymopentin 醋酸酯是一种主要由胸腺皮质和髓质上皮细胞分泌的生物活性肽，也是一种有效的免疫调节剂，具有很短的血浆半衰期（30 秒）。Thymopentin 醋酸酯能够促进自人类胚胎干细胞产生 T 细胞群。

体外研究

Thymopentin 醋酸酯可以增强源自 hESCs 的 T 细胞谱系的生成。

反应信息

• 作为产物：
  描述：

  N-(N-benzyloxycarbonyl-L-valyl)-L-tyrosine methyl ester 在 palladium on activated charcoal sodium hydroxide 、 氢溴酸 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 溶剂黄146 为溶剂， 反应 123.5h， 生成 胸腺五肽醋酸盐
  参考文献：
  名称：

  Martynov, V. F.; Anokhina, V. V.; Belokrylov, G. A., Journal of general chemistry of the USSR, 1989, vol. 59, # 10, p. 2122 - 2128

  摘要：

  DOI：

文献信息

• Tyrosine Bioconjugation through Aqueous Ene-Like Reactions
  申请人：Barbas, III Carlos F.

  公开号：US20120289682A1

  公开（公告）日：2012-11-15

  A new and versatile class of cyclic diazodicarboxamides that reacts efficiently and selectively with phenols and the phenolic side chain of tyrosine through an Ene-like reaction is reported. This mild aqueous tyrosine ligation reaction works over a broad pH range and expands the repertoire of aqueous chemistries available for small molecule, peptide, and protein modification. The tyrosine ligation reactions are shown to be compatible with the labeling of native enzymes and antibodies in buffered aqueous solution. This reaction provides a novel synthetic approach to bispecific antibodies. This reaction will find broad utility in peptide and protein chemistry and in the chemistry of phenol-containing compounds.

  报道了一种新型多功能环状二氮基二羧酰胺类化合物，通过Ene反应与苯酚和酪氨酸的苯基侧链高效选择性反应。这种温和的水相酪氨酸连接反应适用于广泛的pH范围，并扩展了小分子、肽和蛋白质修饰的水相化学反应库。该酪氨酸连接反应可与缓冲水溶液中的天然酶和抗体标记兼容。该反应提供了一种新的双特异性抗体合成方法。该反应将在肽和蛋白质化学以及含酚化合物的化学中发挥广泛的实用价值。
• Enzymatic process for producing immunomodulating pentapeptides and intermediates for use in the process
  申请人：CARLBIOTECH LTD. A/S

  公开号：EP0324659A2

  公开（公告）日：1989-07-19

  Synthesis of peptides Ri-A-B-C-D-E-R2 wherein A, B, C, D and E represent amino acid residues coupled with peptide bonds and A is a ω-amino-or ω-guanidino substituted basic L-or D-amino acid residue or a desamino derivative thereof, B is a (o-amino- or ω-guanidino substituted basic L-amino acid residue, L-Pro or L-dehydroPro, preferably Asp or Glu, C is an acidic L- or D-amino acid residue, preferably Asp or Glu, D is an unpolar, hydrophobic aliphatic or aromatic aryl- or aralkyl group containing L-amino acid residue, preferably Val, lie or Leu, E is an unpolar, hydrophobic aliphatic or aromatic aryl- or aralkyl group containing L- or D-amino acid residue or a decarboxy derivative thereof, preferably Tyr, Trp, Phe, His or Val, Ri is H or an a-amino substituting group, and R2 is OH or an a-carboxy substituting group, by sequential coupling of reactive derivatives of said amino acids and/or by fragment coupling of reactive oligopeptide derivatives on the basis of said amino acids. At least one of these coupling reactions is carried out in a completely or partly aqueous medium at pH 3-12, in the presence of a proteolytic enzyme capable of catalyzing the formation of a peptide which, if desired, is coupled with a reactive amino acid derivative or peptide derivative in the presence of the same or another proteolytic enzyme, further enzymatic or chemical coupling reactions being carried out, if necessary. The process, which is particularly suited for synthesizing the immunomodufating pentapeptides thymopentin and spleninopentin and their analogues, comprises several coupling strategies, the preferred enzymes for use in these strategies i.a. including thermolysin, trypsin, subtilisin, carboxypeptidase Y, elastase and bromelain. The process i.a. uses the intermediates Z1ABOR, Z1ABC(OR')(OR") and Z1ABC(OR)OH, wherein Z1 has the same meaning as Ri, and R is alkyl or benzyl.

  肽的合成 Ri-A-B-C-D-E-R2 其中 A、B、C、D 和 E 代表以肽键连接的氨基酸残基，并且 A 是被ω-氨基或ω-胍基取代的碱性 L-或 D-氨基酸残基或其去氨基衍生物、 B 是邻氨基或ω-胍基取代的碱性 L-氨基酸残基、L-Pro 或 L-脱氢 Pro，最好是 Asp 或 Glu， C 是酸性 L-或 D-氨基酸残基，最好是 Asp 或 Glu， D 是含有 L-氨基酸残基的非极性、疏水性脂肪族或芳香族芳基或芳烷基，最好是 Val、lie 或 Leu、 E是含有 L-或 D-氨基酸残基或其羧基衍生物的非极性、疏水性脂肪族或芳香族芳基或烷基，优选 Tyr、Trp、Phe、His 或 Val，Ri 是 H 或 a-氨基取代基，R2 是 OH 或 a-羧基取代基。 这些偶联反应中至少有一种是在 pH 值为 3-12 的完全或部分水性介质中，在能催化形成肽的蛋白水解酶存在下进行的，如果需要，可在相同或另一种蛋白水解酶存在下与活性氨基酸衍生物或肽衍生物偶联，必要时还可进行进一步的酶或化学偶联反应。 该工艺特别适用于合成免疫调节五肽胸腺五肽和脾脏五肽及其类似物，包括几种偶联策略，在这些策略中使用的首选酶包括热溶解酶、胰蛋白酶、枯草酶、羧肽酶 Y、弹性蛋白酶和菠萝蛋白酶。 工艺 i.a. 使用中间体 Z1ABOR、Z1ABC(OR')(OR") 和 Z1ABC(OR)OH，其中 Z1 的含义与 Ri 相同，R 是烷基或苄基。
• Agent for the atopy prophylaxis
  申请人：Beiersdorf Aktiengesellschaft

  公开号：EP0391218A2

  公开（公告）日：1990-10-10

  Disclosed is an agent for atopy prophylaxis. Supplying gamma-linolenic acid, dihomo-gamma-linolenic acid, the physiologically compatible salts, esters, amides, phospholipids, glycolipids thereof, and Prostaglandin E₁ (PGE₁), PGE₁ derivatives, PGE₁ analogs to babies can prevent a subsequent occurrence of manifest atopy forms. The agents according to the invention are preferably contained in a baby food and/or should be supplied to the baby together therewith. In a further preferred embodiment the agent con­tains thymus hormones, or said hormones are provided in combination with the agent.

  本发明公开了一种用于预防过敏症的制剂。提供 γ-亚麻酸、二氢-γ-亚麻酸、其生理相容的盐、酯、酰胺、磷脂、糖脂和前列腺素 E₁（PGE₁）、PGE₁ 衍生物、PGE₁ 类似物。 给婴儿服用这些药物可以防止随后出现明显的过敏症状。根据本发明的制剂最好包含在婴儿食品中，并且/或者应与婴儿食品一起供应给婴儿。 在另一个优选的实施方案中，制剂含有胸腺激素，或者所述激素与制剂一起提供。
• Stabilizing alkylglycoside compositions and method thereof
  申请人：Aegis Therapeutics, LLC

  公开号：EP2158898A1

  公开（公告）日：2010-03-03

  The present invention relates to alkylglycoside-containing compositions and methods for increasing the stability, reducing the aggregation and immunogenicity, increasing the biological activity, and reducing or preventing fibrillar formation of a peptide, polypeptide, or variant thereof, for example insulin and Peptide T or analog thereof.

  本发明涉及含烷基糖苷的组合物和方法，用于提高肽、多肽或其变体（例如胰岛素和肽 T 或其类似物）的稳定性，降低其聚集性和免疫原性，提高其生物活性，减少或防止其纤维状形成。
• Stabilizing alkylglycoside compositions and methods thereof
  申请人：Aegis Therapeutics, LLC

  公开号：EP2158920A1

  公开（公告）日：2010-03-03

  The present invention relates to alkylglycoside-containing compositions and methods for increasing the stability, reducing the aggregation and immunogenicity, increasing the biological activity, and reducing or preventing fibrillar formation of a peptide, polypeptide, or variant thereof, for example insulin and Peptide T or analog thereof.

  本发明涉及含烷基糖苷的组合物和方法，用于提高肽、多肽或其变体（例如胰岛素和肽 T 或其类似物）的稳定性，降低其聚集性和免疫原性，提高其生物活性，减少或防止其纤维状形成。