N-甲酰基色氨酸 | 27520-72-5

• 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: N-甲酰基色氨酸
• 中文别名: N-甲酰基-L-色氨酸
• 英文名称: N-formyl-L-tryptophan
• 英文别名: N-Formyltryptophan；(2S)-2-formamido-3-(1H-indol-3-yl)propanoic acid
• CAS: 27520-72-5
• 化学式: C₁₂H₁₂N₂O₃
• 分子量: 232.239
• InChiKey: RNEMLJPSSOJRHX-NSHDSACASA-N

物化性质

• 熔点：
  162 °C
• 沸点：
  590.4±45.0 °C(Predicted)
• 密度：
  1.375±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-甲酰基色氨酸 在 (R)-Carvone 、 盐酸 作用下， 以 丙醇 、 水 为溶剂， 反应 0.08h， 以74%的产率得到色胺盐酸盐
  参考文献：
  名称：

  Rapid Conventional and Microwave-Assisted Decarboxylation of L-Histidine and Other Amino Acids via Organocatalysis with R-Carvone Under Superheated Conditions

  摘要：

  This article reports a new methodology taking advantage of superheated chemistry via either microwave or conventional heating for the facile decarboxylation of alpha amino acids using the recoverable organocatalyst, R-carvone. The decarboxylation of amino acids is an important synthetic route to biologically active amines, and traditional methods of amino acid decarboxylation are time consuming (taking up to several days in the case of L-histidine), are narrow in scope, and make use of toxic catalysts. Decarboxylations of amino acids including L-histidine occur in just minutes while replacing toxic catalysts with green catalyst, spearmint oil. Yields are comparable to or exceed previous methods and purification of product ammonium chloride salts is aided by an isomerization reaction of residual catalyst to phenolic carvacrol. The method has been shown to be effective for the decarboxylations of a range of natural, synthetic, and protected amino acids.

  DOI：

  10.1080/00397911.2015.1100745
• 作为产物：
  描述：

  NΑ-甲酰基-DL-色氨酸 在 (1S,2S)-(+)-2-氨基-1-[4-(甲硫基)苯基-1,3-丙二醇 作用下， 生成 N-甲酰基色氨酸
  参考文献：
  名称：

  Process of resolving dl-acyl tryptophan compounds and products obtained thereby

  摘要：

  公开号：

  US02797226A1

文献信息

• [EN] REDOX DEHYDRATION COUPLING CATALYSTS AND METHODS RELATED THERETO<br/>[FR] CATALYSEURS DE COUPLAGE DE DÉSHYDRATATION RÉDOX ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：UNIV EMORY

  公开号：WO2017070157A1

  公开（公告）日：2017-04-27

  This disclosure relates to synthetic coupling methods using catalytic molecules. In certain embodiments, the catalytic molecules comprise heterocyclic thiolamide, S-acylthiosalicylamide, disulfide, selenium containing heterocycle, diselenide compound, ditelluride compound or tellurium containing heterocycle. Catalytic molecules disclosed herein are useful as catalysts in the transformation of hydroxy group containing compounds to amides, esters, ketones, and other carbon to heteroatom or carbon to carbon transformations.

  这份披露涉及使用催化分子的合成偶联方法。在某些实施例中，这些催化分子包括杂环硫酰胺、S-酰基硫代水杨酰胺、二硫化物、含硒杂环、二硒化合物、二碲化合物或含碲杂环。本文披露的催化分子可用作催化剂，用于将含羟基化合物转化为酰胺、酯、酮和其他碳到杂原子或碳到碳的转化过程中。
• Formyloxyacetoxyphenylmethane as an <i>N</i>-Formylating Reagent for Amines, Amino Acids, and Peptides
  作者：Robert S. L. Chapman、Ruth Lawrence、Jonathan M. J. Williams、Steven D. Bull

  DOI：10.1021/acs.orglett.7b02382

  日期：2017.9.15

  Formyloxyacetoxyphenylmethane is a stable, water-tolerant, N-formylating reagent for primary and secondary amines that can be used under solvent-free conditions at room temperature to prepare a range of N-formamides, N-formylanilines, N-formyl-α-amino acids, N-formylpeptides, and an isocyanide.

  Formyloxyacetoxyphenylmethane是一种稳定的，水耐受性，Ñ对于可以无溶剂的条件下在室温下可用于制备一系列的伯和仲胺-formylating试剂Ñ -formamides，Ñ -formylanilines，Ñ甲酰基α氨基酸，N-甲酰基肽和异氰化物。
• Chiral β₃-isocyanopropionates for multicomponent synthesis of peptides and depsipeptides containing a β-amino acid fragment
  作者：Danil P. Zarezin、Olga I. Shmatova、Valentine G. Nenajdenko

  DOI：10.1039/c8ob01507d

  日期：——

  An efficient three-step synthesis of a novel family of enantiomerically pure isocyanides derived from β3-isocyanopropionic acids was elaborated. Easily available N-formylated α-amino acids were used as starting materials towards this aim. The 3-step sequence (Arndt–Eistert reaction–Wolff rearrangement–dehydration) resulted in target isonitriles in good yields (up to 97%). As a result a new family of

  新家族从β衍生的对映体纯的异腈的有效的三步合成3个-isocyanopropionic酸得到阐述。容易获得的N-甲酰化的α-氨基酸被用作实现该目标的原料。3步序列（Arndt-Eistert反应-Wolff重排-脱水）导致目标异腈具有良好的收率（高达97％）。其结果是异氰化物轴承β片段的新家族3得到的α-氨基酸具有不同官能团（酰胺，酯和短肽）。已证明这些新的异腈可用于Ugi和Passerini反应中，以制备掺入β-氨基酸片段的短肽和二肽。
• [EN] COMPSTATIN ANALOGS WITH IMPROVED POTENCY AND PHARMACOKINETIC PROPERTIES<br/>[FR] ANALOGUES DE COMPSTATINE DE PUISSANCE ET DE PROPRIÉTÉS PHARMACOCINÉTIQUES AMÉLIORÉES
  申请人：UNIV PENNSYLVANIA

  公开号：WO2015142701A1

  公开（公告）日：2015-09-24

  Compounds comprising peptides capable of binding C3 protein and inhibiting complement activation are disclosed. The compounds include a modified compstatin peptide or analog thereof, comprising an added N-terminal component that improves (1) the binding affinity of the peptide to C3, C3b or C3c and/or (2) the plasma stability and/or plasma residence time of the peptide, as compared with an unmodified compstatin peptide under equivalent conditions. Methods of improving the C3 binding of compstatin or compstatin analogs are also disclosed, as well as methods of designing compstatin analogs with improved C3 binding.

  本发明涉及包含能够结合C3蛋白并抑制补体激活的肽的化合物。这些化合物包括一种经过修改的compstatin肽或其类似物，其中包括一个添加的N-末端组分，该组分改善了肽与C3、C3b或C3c的结合亲和力和/或与未经修改的compstatin肽在等效条件下相比的血浆稳定性和/或血浆停留时间。还公开了改善compstatin或compstatin类似物的C3结合的方法，以及设计具有改善C3结合的compstatin类似物的方法。
• Cysteine thiol-protected peptides for use in immunoassays
  申请人：——

  公开号：US20030215788A1

  公开（公告）日：2003-11-20

  Peptides immunoreactive with antibodies to native proteins, and which have at least two cysteine residues that contribute to mimicking an epitope of the protein, are prepared with the cysteine thiol groups protected. When deprotected, the peptides have enhanced immunoreactivity. The peptides are particularly useful for detecting antibodies or antigens associated with retroviruses, including the clinically important lymphotropic retroviruses HIV-1, HIV-2, HTLV-I, and HTLV-II

  具有至少两个半胱氨酸残基，与天然蛋白质抗体免疫反应，且有助于模拟蛋白质表位的肽，使用半胱氨酸巯基保护，制备出来的肽具有增强的免疫反应性。这些肽特别适用于检测与逆转录病毒相关的抗体或抗原，包括临床重要的淋巴病毒HIV-1、HIV-2、HTLV-I和HTLV-II。