L-鲸肌肽 | 331-38-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 中文名称: L-鲸肌肽
• 英文名称: L-anserine
• 英文别名: (+)-balenine；L-balenine；Anserine；Ophidine；(2S)-2-(3-azaniumylpropanoylamino)-3-(1-methylimidazol-4-yl)propanoate
• CAS: 331-38-4
• 化学式: C₁₀H₁₆N₄O₃
• 分子量: 240.262
• InChiKey: SLRNWACWRVGMKD-QMMMGPOBSA-N

物化性质

• 溶解度：
  甲醇（微溶）、水（微溶）
• 沸点：
  611.3±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为产物：
  描述：

  S-(+)-7-Methoxycarbonyl-5,6,7,8-tetrahydroimidazo<1,5-c>pyrimidin-5-on 在 N-甲基吗啉 、 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 118.0h， 生成 L-鲸肌肽
  参考文献：
  名称：

  Carnosine protects cardiac myocytes against lipid peroxidation products

  摘要：

  Endogenous histidyl dipeptides such as carnosine (-alanine-l-histidine) form conjugates with lipid peroxidation products such as 4-hydroxy-trans-2-nonenal (HNE and acrolein), chelate metals, and protect against myocardial ischemic injury. Nevertheless, it is unclear whether these peptides protect against cardiac injury by directly reacting with lipid peroxidation products. Hence, to examine whether changes in the structure of carnosine could affect its aldehyde reactivity and metal chelating ability, we synthesized methylated analogs of carnosine, balenine (-alanine-N-methylhistidine) and dimethyl balenine (DMB), and measured their aldehyde reactivity and metal chelating properties. We found that methylation of N residue of imidazole ring (balenine) or trimethylation of carnosine backbone at N residue of imidazole ring and terminal amine group dimethyl balenine (DMB) abolishes the ability of these peptides to react with HNE. Incubation of balenine with acrolein resulted in the formation of single product (m/z 297), whereas DMB did not react with acrolein. In comparison with carnosine, balenine exhibited moderate acrolein quenching capacity. The Fe2+ chelating ability of balenine was higher than that of carnosine, whereas DMB lacked chelating capacity. Pretreatment of cardiac myocytes with carnosine increased the mean lifetime of myocytes superfused with HNE or acrolein compared with balenine or DMB. Collectively, these results suggest that carnosine protects cardiac myocytes against HNE and acrolein toxicity by directly reacting with these aldehydes. This reaction involves both the amino group of -alanyl residue and the imidazole residue of l-histidine. Methylation of these sites prevents or abolishes the aldehyde reactivity of carnosine, alters its metal-chelating property, and diminishes its ability to prevent electrophilic injury.

  DOI：

  10.1007/s00726-018-2676-6

文献信息

• 一种N(π)-甲基-L-组氨酸衍生物的制备方法及其在合成鲸肌肽中的应用
  申请人：南京纽邦生物科技有限公司

  公开号：CN108997187A

  公开（公告）日：2018-12-14

  本发明涉及一种N(π)‑甲基‑L‑组氨酸衍生物的制备方法，以及由合成的N(π)‑甲基‑L‑组氨酸衍生物制备鹅肌肽的方法，本发明所述方法原辅料廉价易得，选择性好，收率高；操作简单易行、工艺稳定、易于控制、反应后处理方便、产物收率好，纯度高，可以经济方便地用于工业化生产。
• Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction
  作者：Toshiyuki Kan、Megumi Yamashita、Keita Shimizu、Yasuaki Koizumi、Toshiyuki Wakimoto、Yoshitaka Hamashima、Tomohiro Asakawa、Makoto Inai

  DOI：10.1055/s-0035-1562796

  日期：——

  A concise synthesis of anserine and related compounds was accomplished by Et-DuPhos-Rh-catalyzed asymmetric hydrogenation of dehydrohistidine derivatives in 2,2,2-trifluoroethanol, which played a key role in improving the yield and selectivity.

  通过 Et-DuPhos-Rh 催化脱氢组氨酸衍生物在 2,2,2-三氟乙醇中的不对称加氢，实现了鹅丝氨酸及相关化合物的简洁合成，这对提高产率和选择性起到了关键作用。
• NOVEL HISTIDINE DERIVATIVES
  申请人：Nakazawa Yoshitaka

  公开号：US20100152459A1

  公开（公告）日：2010-06-17

  The present invention is to provide a novel compound which is useful as a pharmaceutical agent such as an analgesic. The present invention is to provide the novel histidine derivative having an excellent analgesic action and the like. The compound of the present invention has a very high intermigration into the blood upon oral administration and is very useful as a pharmaceutical agent, especially an analgesic for the treatment of acute or chronic pain diseases and of neuropathic pain diseases.

  本发明提供了一种新型化合物，可用作药物剂，如镇痛剂。本发明提供了具有出色镇痛作用的新型组氨酸衍生物等。本发明的化合物在口服后能够迅速进入血液循环，并且非常适用作为药物剂，特别是用于治疗急性或慢性疼痛疾病和神经病理性疼痛疾病的镇痛剂。
• Stable aqueous compositions comprising amide-protected bioactive creatine species and uses thereof
  申请人：Owoc, John H.

  公开号：EP2377578A1

  公开（公告）日：2011-10-19

  The present invention provides amide-protected creatine molecules and compositions, containing one or more bioactive forms of creatine in aqueous compositions, wherein bioactive forms of creatine do not appreciably degrade into creatinine. Also provided are various beneficial effects of administering aqueous compositions having at least one amide-protected creatine molecule.

  本发明提供了酰胺保护的肌酸分子和组合物，其中包含一种或多种生物活性形式的肌酸在水性组合物中，其中生物活性形式的肌酸不会明显降解为肌酸酐。同时提供了在至少含有一种酰胺保护的肌酸分子的水性组合物中给予的各种有益效果。
• 一种鹅肌肽及其中间体的制备方法
  申请人：南京纽邦生物科技有限公司

  公开号：CN109748874A

  公开（公告）日：2019-05-14

  本发明提供了两种鹅肌肽的制备方法，以及一种合成鹅肌肽中间体的制备方法，操作简单易行、工艺稳定、易于控制、反应后处理方便、产物收率好，纯度高，可以经济方便地用于工业化生产。