O-[N-(9H-fluoren-9-ylmethoxycarbonyl)-L-prolyl]glycolic acid | 131228-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: O-[N-(9H-fluoren-9-ylmethoxycarbonyl)-L-prolyl]glycolic acid
• 英文别名: (9-fluorenylmethoxycarbonyl)-L-prolylglycolic acid；(S)-2-((1-(((9H-fluoren-9-yl)methoxy)carbonyl)pyrrolidin-2-carbonyl)oxy)acetic acid；2-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]oxyacetic acid
• CAS: 131228-94-9
• 化学式: C₂₂H₂₁NO₆
• 分子量: 395.412
• InChiKey: NSERYVHZQRDIQX-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  phenacyl (9-fluorenylmethoxycarbonyl)-L-prolylglycolate 在 水 、 溶剂黄146 、 锌 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 生成 O-[N-(9H-fluoren-9-ylmethoxycarbonyl)-L-prolyl]glycolic acid
  参考文献：
  名称：

  Direct cleavage of peptides from a solid support into aqueous buffer. Application in simultaneous multiple peptide synthesis

  摘要：

  A method of simultaneous multiple peptide synthesis which integrates synthesis, side-chain deprotection, cleavage, and purification so as to afford peptide solutions suitable for immediate biological testing is described. The approach utilizes a novel diketopiperazine-forming cleavable linker 1. Upon side-chain deprotection, 1 gives 2, which is stable to a protocol designed to remove contaminants from the support-bound peptide prior to cleavage. Peptide cleavage is then effected by treating 2 with a neutral or near neutral buffer to give peptide 4, which carries a C-terminal diketopiperazine moiety, in good yield. In this study the glycolamido and 4-(oxymethyl)benzamido esters of 1 have been appraised. The approach is demonstrated in model studies on 7 and 8 and in the preparation and characterization of peptides 17-21. The general approach allows 10-100-nmol quantities of many hundreds of peptides to be concurrently prepared in a relatively short period of time when used in conjunction with the multipin method of multiple peptide synthesis.

  DOI：

  10.1021/jo00023a035

文献信息

• Peptide Bond Isosteres:  Ester or (<i>E</i>)-Alkene in the Backbone of the Collagen Triple Helix
  作者：Cara L. Jenkins、Melissa M. Vasbinder、Scott J. Miller、Ronald T. Raines

  DOI：10.1021/ol050780m

  日期：2005.6.1

  [structure: see text] Collagen is the most abundant protein in animals. Interstrand N-H...O=C hydrogen bonds between backbone amide groups form a ladder in the middle of the collagen triple helix. Isosteric replacement of the hydrogen-bond-donating amide with an ester or (E)-alkene markedly decreases the conformational stability of the triple helix. Thus, this recurring hydrogen bond is critical to the

  [结构：参见文字]胶原蛋白是动物中最丰富的蛋白质。主链酰胺基团之间的链间NH ... O = C氢键在胶原三螺旋的中间形成一个阶梯。用酯或（E）-烯烃的等氢取代给氢键的酰胺显着降低了三螺旋的构象稳定性。因此，这种重复的氢键对于胶原蛋白的结构完整性至关重要。在这种情况下，与（E）-链烯相比，酯-等排烷酯具有更高的稳定性。
• Improved solid phase synthesis of peptide carboxyamidomethyl (Cam) esters for enzymatic segment condensation
  作者：Timo Nuijens、Ana Toplak、Mathijs B.A.C. van de Meulenreek、Marcel Schmidt、Michel Goldbach、Peter J.L.M. Quaedflieg

  DOI：10.1016/j.tetlet.2016.06.132

  日期：2016.8

  based on the coupling of hydroxyl protected glycolic acid to a solid support, followed by ester synthesis using an N-protected amino acid and dicyclohexyl carbodiimide with catalytic 4-dimethylaminopyridine. The second type is based on the synthesis of amino acid carboxymethyl ester building blocks, which are coupled to the solid support using standard coupling reagents and procedures. The latter procedure

  肽C末端羧酰胺甲基（Cam-）酯是酶段缩合的关键组成部分，其收率和纯度对于该策略的整体效率至关重要。尽管已经公开了一些制备它们的方法，但是肽C-末端Cam-酯的固相合成并不简单。在这里，我们描述了两种新颖的方法类型，它们以高收率和良好的纯度进行合成。第一类是基于羟基保护的乙醇酸与固体载体的偶联，然后使用N保护的氨基酸和二环己基碳二亚胺与催化的4-二甲基氨基吡啶进行酯合成。第二种是基于氨基酸羧甲基酯结构单元的合成，其使用标准偶联剂和方法偶联至固体支持物。
• 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。
• Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs
  作者：Anton Agarkov、Scott J. Greenfield、Takahiro Ohishi、Scott E. Collibee、Scott R. Gilbertson

  DOI：10.1021/jo049103g

  日期：2004.11.1

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.