methyl (S)-2-acetamidobut-3-enoate | 820220-49-3

• 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: methyl (S)-2-acetamidobut-3-enoate
• 英文别名: N-acetyl-vinylglycine methyl ester；N-acetyl-Vgl methyl ester；Ac-Vgl-OMe；Methyl (2S)-2-acetamidobut-3-enoate
• CAS: 820220-49-3
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: DLUNQFFKPOIAOQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-2-acetamidobut-3-enoate 在 ammonium hypophosphite 、 三乙基硼 、 氧气 作用下， 以 甲醇 、 hexanes 为溶剂， 生成
  参考文献：
  名称：

  Syntheses of the P-Methylase Substrates of the Bialaphos Biosynthetic Pathway

  摘要：

  Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.

  DOI：

  10.1021/ol802269x
• 作为产物：
  描述：

  methyl (S)-2-acetamido-4-(phenylselenyl)butanoate 在 silica gel supported NaIO₄ 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以81%的产率得到methyl (S)-2-acetamidobut-3-enoate
  参考文献：
  名称：

  Syntheses of the P-Methylase Substrates of the Bialaphos Biosynthetic Pathway

  摘要：

  Genetic studies suggest that either N-acetyldemethyl phosphinothricin (1, N-AcDMPT) or N-acetyldemethyl phosphinothricin tripeptide (2, N-AcDMPTT) is the substrate for the P-methylation reaction in the biosynthesis of phosphinothricin tripeptide (PTT), which is widely used as an herbicide. To study the mechanism for this unique P-methylation reaction catalyzed by the BcpD protein and the functions of the unusual nonribosomal peptide synthetases involved in PTT biosynthesis, this work reports the chemical syntheses of 1 and 2.

  DOI：

  10.1021/ol802269x

文献信息

• [EN] SUBSTITUTED 1,3-PHENYL HETEROARYL DERIVATIVES AND THEIR USE IN THE TREATMENT OF DISEASE<br/>[FR] DÉRIVÉS DE 1,3-PHÉNYL HÉTÉROARYLE SUBSTITUÉS ET LEUR UTILISATION DANS LE TRAITEMENT D'UNE MALADIE
  申请人：NOVARTIS AG

  公开号：WO2021038426A1

  公开（公告）日：2021-03-04

  The invention relates to heterocyclic compounds of the formula (I) in which all of the variables are as defined in the specification; capable of modulating the ctivity of TMEM16a. The invention further provides a method for manufacturing compounds of the invention, and its therapeutic uses. The invention further provides methods to their preparation, to their medical use, in particular to their use in the treatment and management of diseases or disorders including COPD, bronchiectasis, asthma, cystic fibrosis, primary ciliary dyskinesia, chronic bronchitis, cystic fibrosis, primary ciliary dyskinesia, respiratory tract infections (acute and chronic; viral and bacterial), lung carcinoma.

  该发明涉及公式（I）中的杂环化合物，其中所有变量均如规范中定义；能够调节TMEM16a的活性。该发明进一步提供了一种制造该发明化合物的方法及其治疗用途。该发明还提供了它们的制备方法，医学用途，特别是在治疗和管理包括COPD、支气管扩张、哮喘、囊性纤维化、原发性纤毛运动障碍、慢性支气管炎、肺部感染（急性和慢性；病毒和细菌性）、肺癌等疾病或疾病的用途。
• Ribosomal synthesis of dehydrobutyrine- and methyllanthionine-containing peptides
  作者：Yuki Goto、Kazuhiro Iwasaki、Kohei Torikai、Hiroshi Murakami、Hiroaki Suga

  DOI：10.1039/b904314d

  日期：——

  We report here the ribosomal synthesis of methyllanthionine-containing cyclic peptides involving a site-specific incorporation of vinylglycine under the reprogrammed genetic code, followed by the isomerization of the vinylglycine to dehydrobutyrine, and the subsequent intramolecular Michael addition of a cysteine residue placed at a downstream position of the vinylglycine.

  我们在此报告了含甲基黄嘌呤环肽的核糖体合成过程，包括在重编遗传密码下特异性地加入乙烯基甘氨酸，然后将乙烯基甘氨酸异构化为脱氢丁炔，随后在乙烯基甘氨酸的下游位置与半胱氨酸残基进行分子内迈克尔加成。
• Small Molecule Inhibitors of Ghrelin O-Acyltransferase
  申请人：Harran Patrick G.

  公开号：US20110318807A1

  公开（公告）日：2011-12-29

  Ghrelin O-acyltransferase (GOAT) is inhibited with designed small molecules. Methods comprise contacting the GOAT with an inhibitor and detecting a resultant inhibition.

  Ghrelin O-acyltransferase（GOAT）被设计的小分子抑制。方法包括将抑制剂与GOAT接触并检测所产生的抑制作用。
• US8329745B2
  申请人：——

  公开号：US8329745B2

  公开（公告）日：2012-12-11
• [EN] PREPARATION OF GLYCOSYLATED AMINO ACIDS, PROTEINS AND PEPTIDES VIA OLEFIN METATHESIS REACTIONS<br/>[FR] PREPARATION D'ACIDES AMINES, DE PROTEINES ET DE PEPTIDES GLYCOSYLES AU MOYEN DE REACTIONS DE METATHESE D'OLEFINES
  申请人：ISIS INNOVATION

  公开号：WO2005000873A1

  公开（公告）日：2005-01-06

  A method for the preparation of a glycosylated amino acid, protein or peptide, the method comprising reacting an unprotected carbohydrate compound containing a carbon-carbon double bond with an amino acid, a protein or a peptide containing a side-chain carbon-carbon double bond under conditions whereby olefin metathesis occurs. Preferably the method takes place in a protic solvent, and the carbohydrate compound is an allyl or vinyl C-glycoside.