Nalpha-乙酰基-L-组氨酸甲基酰胺 | 6367-11-9

• 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: Nalpha-乙酰基-L-组氨酸甲基酰胺
• 英文名称: Ac-L-His-NHMe
• 英文别名: N-Acetyl-L-histidinmethylamid；N-Acetyl-L-histinmethylamid；N-Acetyl-histidin-methylamid；N^α-acetyl-histidine methylamide；N^α-acetyl-L-histidine-methylamide；N^α-Acetyl-L-histidin-methylamid；AC-HIS-NHME；(2S)-2-acetamido-3-(1H-imidazol-5-yl)-N-methylpropanamide
• CAS: 6367-11-9
• 化学式: C₉H₁₄N₄O₂
• mdl: MFCD00237489
• 分子量: 210.236
• InChiKey: XWLRQKZOVSBKSE-QMMMGPOBSA-N

物化性质

• 熔点：
  242-247°C
• 溶解度：
  可溶于DMSO（轻微加热）、甲醇（轻微）、水（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

反应信息

• 作为产物：
  描述：

  N-乙酰-L-组氨酸 在 甲醇 、 氯化亚砜 作用下， 生成 Nalpha-乙酰基-L-组氨酸甲基酰胺
  参考文献：
  名称：

  The Interaction of α-Chymotrypsin with a Series of α-N-Acetyl-α-amino Acid Methylamides¹

  摘要：

  DOI：

  10.1021/ja01518a050

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。
• SIEMION, IGNACY Z.;PICUR, BOLESLAW, BULL. POL. ACAD. SCI. CHEM., 35,(1987) N 5-6, 179-186
  作者：SIEMION, IGNACY Z.、PICUR, BOLESLAW

  DOI：——

  日期：——
• US8765920B2
  申请人：——

  公开号：US8765920B2

  公开（公告）日：2014-07-01
• [EN] TYROSINE BIOCONJUGATION THROUGH AQUEOUS ENE-LIKE REACTIONS<br/>[FR] BIOCONJUGAISON DE LA TYROSINE PAR DES RÉACTIONS DE TYPE ÈNE EN MILIEU AQUEUX
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2011079315A1

  公开（公告）日：2011-06-30

  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.
• The Interaction of α-Chymotrypsin with a Series of α-N-Acetyl-α-amino Acid Methylamides¹
  作者：Thomas H. Applewhite、Carl Niemann

  DOI：10.1021/ja01518a050

  日期：1959.5