Fmoc-N-methyl-L-serine | 291311-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-N-methyl-L-serine
• 英文别名: Fmoc-N-methyl-serine；Fmoc-N-Me-Ser-OH；(2S)-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]-3-hydroxypropanoic acid
• CAS: 291311-48-3
• 化学式: C₁₉H₁₉NO₅
• 分子量: 341.364
• InChiKey: ZVWHTEOKMWNXGP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-N-methyl-L-serine 在 三氟化硼乙醚 、 达卡巴嗪 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 (S)-2-[(9H-Fluoren-9-ylmethoxycarbonyl)-methyl-amino]-3-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-propionic acid pentafluorophenyl ester
  参考文献：
  名称：

  Deacetylation of Nα-methylated glycopeptides reveals that aza-enolates provide protection against β-elimination of carbohydrates O-linked to serine

  摘要：

  Three glycopeptides Ac-Ala-Ser[beta-Gal(OAc)(4)]-Phe-NH2, Ac-Ala-N-alpha-Me-Ser[beta-Gal(OAc)(4)]-Phe-NH2 and Ac-Ala-Ser[beta-Gal(OAc)(4)]-N-alpha-Me-Phe-NH2 have been prepared and treated with base in order to remove the O-acetyl protective groups. The glycopeptide which carried the N-methyl group on the glycosylated serine, was substantially more susceptible to beta-elimination than the two others. This reveals that formation of an aza-enolate from the amide bond to a glycosylated serine provides protection against p-elimination under basic conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00611-0
• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl (4S)-4-(acetyloxymethyl)-5-oxo-1,3-oxazolidine-3-carboxylate 在 盐酸 、 三氯化铝 、 三异丙基硅烷 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 Fmoc-N-methyl-L-serine
  参考文献：
  名称：

  An improved synthesis of Fmoc-N-methyl serine and threonine

  摘要：

  An improved method for the synthesis of Fmoc-N-methyl serine and threonine has been developed, which involves formation and subsequent reduction of the corresponding oxazolidinone with a Lewis acid under mild conditions, with improved yields and shorter reaction times. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.112

文献信息

• Assembly of the TAN-1057 A/B Heterocycle from a Dehydroalanine Precursor
  作者：Peishan Lin、A. Ganesan

  DOI：10.1055/s-2000-8713

  日期：——

  A tandem reaction process was used to form the tetrahydropyrimidinone core of the TAN-1057 A and B dipeptide antibiotics. Michael addition of ammonia to a dehydroalanine derivative, followed by intramolecular displacement of an S-methylisothiourea assembles the tetrahydropyrimidinone in one-step.

  采用串联反应过程形成了TAN-1057 A和B二肽抗生素的四氢吡咯啉酮核心。氨对去氨基丙氨酸衍生物的迈克尔加成，随后S-甲基异硫脲的分子内取代，在一步中组装了四氢吡咯啉酮。
• Antiplasmodial activity of short peptide-based compounds
  作者：Amit Mahindra、Rahul P. Gangwal、Sunil Bansal、Nathan E. Goldfarb、Ben M. Dunn、Abhay T. Sangamwar、Rahul Jain

  DOI：10.1039/c5ra00779h

  日期：——

  Three series of short peptide-based compounds were synthesized, which upon evaluation against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains ofPlasmodium falciparum in vitro, produced IC₅₀values ranging between 1.4–4.7 μg mL⁻¹.

  合成了三系列基于短肽的化合物，经评估对疟原虫Plasmodium falciparum的氯喹敏感（D6）和氯喹耐药（W2）菌株进行体外实验，产生的IC₅₀值范围在1.4-4.7 μg mL⁻¹之间。
• PEPTIDE-COMPOUND CYCLIZATION METHOD
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20150080549A1

  公开（公告）日：2015-03-19

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.

  本发明的目的是提供一种发现对于难以处理的靶点有效的药物的方法，这些药物通常很难被发现。本发明涉及新型的环化肽化合物的方法，以及包含这些化合物的新型肽库，以实现上述目的。
• Peptide-compound cyclization method
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US09409952B2

  公开（公告）日：2016-08-09

  An object of the present invention is to provide methods of discovering drugs effective for tough targets, which have conventionally been discovered only with difficulty. The present invention relates to novel methods for cyclizing peptide compounds, and novel peptide compounds and libraries comprising the same, to achieve the above object.

  本发明的目的是提供发现对于难以发现的药物目标有效的药物的方法，这些药物目标通常很难被发现。本发明涉及新型的循环肽化合物的方法，以及包含这些化合物的新型肽库，以达到上述目的。
• CYCLIC PEPTIDE COMPOUND HAVING HIGH MEMBRANE PERMEABILITY, AND LIBRARY CONTAINING SAME
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP3636807A1

  公开（公告）日：2020-04-15

  The present inventors have found that when screening for cyclic peptide compounds that can specifically bind to a target molecule, the use of a library including cyclic peptide compounds having a long side chain in the cyclic portion can improve the hit rate for cyclic peptide compounds that can specifically bind to the target molecule. Meanwhile, the present inventors have found that tryptophan and tyrosine residues, which have conventionally been used in oral low molecular-weight pharmaceuticals and are amino acid residues having an indole skeleton or a hydroxyphenyl group, are not suitable for peptides intended to attain high membrane permeability.

  本发明人发现，在筛选能与目标分子特异性结合的环肽化合物时，使用包括环状部分具有长侧链的环肽化合物库，可以提高能与目标分子特异性结合的环肽化合物的命中率。同时，本发明者发现色氨酸和酪氨酸残基不适合用于旨在获得高膜渗透性的肽，这两种残基通常用于口服低分子量药物，是具有吲哚骨架或羟基苯基的氨基酸残基。