1,1’,1“-(1,3,5-triazinane-1,3,5-triyl)tris(2-bromoethanone) | 92531-02-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪烷类
• 英文名称: 1,1’,1“-(1,3,5-triazinane-1,3,5-triyl)tris(2-bromoethanone)
• 英文别名: 1,1′,1″-(1,3,5-triazinane-1,3,5-triyl)tris(2-bromoethan-1-one)；1,1',1''-(1,3,5-triazinan-1,3,5-triyl)tris(2-bromoethanon)；CCDC 1516968；TATB；1,1',1''-(1,3,5-Triazinane-1,3,5-triyl)tris(2-bromoethan-1-one)；1-[3,5-bis(2-bromoacetyl)-1,3,5-triazinan-1-yl]-2-bromoethanone
• CAS: 92531-02-7
• 化学式: C₉H₁₂Br₃N₃O₃
• 分子量: 449.925
• InChiKey: WQGMKAOQIJBHRG-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C (decomp)
• 沸点：
  595.7±50.0 °C(Predicted)
• 密度：
  2.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1’,1“-(1,3,5-triazinane-1,3,5-triyl)tris(2-bromoethanone) 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以82%的产率得到1,1′,1″-(1,3,5-triazinane-1,3,5-triyl)tris(2-azidoethan-1-one)
  参考文献：
  名称：

  蛋白质的原位环化（INCYPRO）：交联衍生化可调节蛋白质的稳定性。

  摘要：

  蛋白质大环化代表增加蛋白质三级结构稳定性的非常有效的策略。在这里，我们描述了一组新颖的C3对称三亲电子试剂及其用于蛋白质环化的用途。这些亲电试剂与包含三个溶剂暴露的半胱氨酸残基的蛋白质结构域反应，导致蛋白质原位环化（INCYPRO）。我们观察到交联速率对亲电性有明显的依赖性。与线性前体相比，所有九种获得的交联蛋白均显示出显着提高的热稳定性（最高可增加29°C的熔解温度）。最有趣的是，稳定度与交联的亲水性相关。

  DOI：

  10.1021/acs.joc.9b02490
• 作为产物：
  描述：

  三聚甲醛 、 溴乙腈 在 硫酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.25h， 以95%的产率得到1,1’,1“-(1,3,5-triazinane-1,3,5-triyl)tris(2-bromoethanone)
  参考文献：
  名称：

  极性铰链作为（双）环肽中的功能性构象约束。

  摘要：

  自行车/环肽工具包：已开发出两个用于肽环化的极性铰链，从而导致双环肽和环化肽具有更高的溶解度和生物活性。新的铰链也可能在肽上施加不同的构象，这使它们成为合成（双）环肽组合文库的有吸引力的试剂。

  DOI：

  10.1002/cbic.201600612

文献信息

• [EN] A METHOD FOR MODIFICATION OF PEPTIDES IMMOBILIZED ON A SOLID SUPPORT BY TRACELESS REDUCTIVELY CLEAVABLE LINKER MOLECULES<br/>[FR] PROCÉDÉ DE MODIFICATION DE PEPTIDES IMMOBILISÉS SUR UN SUPPORT SOLIDE PAR DES MOLÉCULES DE LIAISON POUVANT ÊTRE CLIVÉES PAR RÉDUCTION SANS TRACE
  申请人：BELYNTIC GMBH

  公开号：WO2021023892A1

  公开（公告）日：2021-02-11

  The present invention relates to a method for modifying and purifying peptides comprising an immobilizing step, a modification step and a releasing step. In the immobilizing step, a crude linker-tagged peptide L-P is coupled to a solid support yielding an immobilized linker-tagged peptide S-L-P. Subsequently, the immobilized linker-tagged peptide S-L-P is modified with one or more organic molecules yielding an immobilized linker-tagged peptide S-L-mP. Finally, the modified peptide is released via a reduced intermediate RI. The linker molecule is a compound of formula 1, X-Tb-Va-U-Y-Z (1), which can be coupled to a purification resin via the moiety X and to a peptide via the moiety Y under the release of the leaving group Z. T is an optional spacer moiety and V is an optional electron withdrawing moiety. U is an aryl or 5- or 6-membered heteroaryl moiety bound to at least one electron withdrawing moiety V, W or E. The linker is stable under acidic conditions and releases the peptide upon addition of a reducing agent.

  本发明涉及一种修饰和纯化肽的方法，包括固定步骤、修饰步骤和释放步骤。在固定步骤中，将粗链联标记的肽L-P偶联到固体支持上，得到固定的链联标记的肽S-L-P。随后，用一个或多个有机分子修饰固定的链联标记的肽S-L-P，得到固定的链联标记的肽S-L-mP。最后，通过还原中间体RI释放修饰的肽。链联分子是化合物1的化学式，X-Tb-Va-U-Y-Z（1），可以通过基团X偶联到纯化树脂，通过基团Y偶联到肽，释放离去基团Z。T是可选的间隔基团，V是可选的电子吸引基团。U是芳基或与至少一个电子吸引基团V、W或E结合的芳基或5-或6-成员杂芳基基团。该链联在酸性条件下稳定，并在加入还原剂后释放肽。
• AGADZHANYAN, TS. E.;MINASYAN, G. G., ARM. XIM. ZH., 1984, 37, N 3, 185-188
  作者：AGADZHANYAN, TS. E.、MINASYAN, G. G.

  DOI：——

  日期：——
• NOVEL lNHIBITORS OF THE ENZYME ACTIVATED FACTOR XII (FXIIA)
  申请人：ECOLE POLYTECHNIQUE FEDERALE DE LAUSANNE (EPFL)

  公开号：US20180118786A1

  公开（公告）日：2018-05-03

  The present invention relates to a bicyclic inhibitor of the coagulation enzyme activated factor XII (FXIIa) comprising or consisting of the peptide) (X 1 )(X 2 )(X 3 ) n (X 4 )RL(X 5 )(X 6 ) m (X 7 )(X 9 ) l (X 10 )(X 11 )(X 12 )(X 13 )(X 14 ) k (X 15 )(X 16 ), wherein (X 1 ) is present or absent and, if present, is an amino acid; (X 2 ) is an amino acid with a side chain; (X 3 ) is an amino acid and n is between 0 and 3, preferably 0 or 1 and most preferably 0; (X 4 ) is an aliphatic L-amino acid or a cyclic L-amino acid, preferably L, P or an aromatic L-amino acid, and most preferably an aromatic L-amino acid; (X 5 ) is an amino acid; (X 6 ) is an amino acid and m is between 0 and 3, preferably 0 or 1 and most preferably 0; (X 7 ) is an amino acid with a side chain; (X 9 ) is an amino acid and l is between 0 and 3, preferably 0 or 1 and most preferably 0; (X 10 ) is an amino acid; (X 11 ) is an amino acid, preferably Q; (X 12 ) is a hydrophobic L-amino acid, preferably an aliphatic L-amino acid, and is most preferably L; (X 13 ) is an amino acid; (X 14 ) is an amino acid and k is between 0 and 3, preferably 0 or 1 and most preferably 0, (X 15 ) is an amino acid with a side chain; and (X 16 ) is present or absent and, if present, is an amino acid; and wherein the side chains of (X 2 ), (X 7 ) and (X 15 ) are connected via a connecting molecule, said connecting molecule having at least three functional groups, each functional group forming a covalent bond with one of the side chains of (X 2 ), (X 7 ) and (X 15 ).
• US4128538A
  申请人：——

  公开号：US4128538A

  公开（公告）日：1978-12-05
• [EN] NOVEL INHIBITORS OF THE ENZYME ACTIVATED FACTOR XII (FXIIA)<br/>[FR] NOUVEAUX INHIBITEURS DU FACTEUR XII À ACTIVATION ENZYMATIQUE (FXIIA)
  申请人：ECOLE POLYTECHNIQUE FÉDÉRALE DE LAUSANNE (EPFL)

  公开号：WO2016174103A1

  公开（公告）日：2016-11-03

  The present invention relates to a bicyclic inhibitor of the coagulation enzyme activated factor XII (FXIIa) comprising or consisting of the peptide (X1)(X2)(X3)n(X4)(X5)(X6)m(X7)(X9)l(X10)(X11)(X12)(X13)(X14)k(X15)(X16), wherein (X1) is present or absent and, if present, is an amino acid; (X2) is an amino acid with a side chain; (X3) is an amino acid and n is between 0 and 3, preferably 0 or 1 and most preferably 0; (X4) is an aliphatic L-amino acid or a cyclic L- amino acid, preferably L, P or an aromatic L-amino acid, and most preferably an aromatic L-amino acid; (X5) is an amino acid; (X6) is an amino acid and m is between 0 and 3, preferably 0 or 1 and most preferably 0; (X7) is an amino acid with a side chain; (X9) is an amino acid and I is between 0 and 3, preferably 0 or 1 and most preferably 0; (X10) is an amino acid; (X11) is an amino acid, preferably Q; (X12) is a hydrophobic L-amino acid, preferably an aliphatic L-amino acid, and is most preferably L; (X13) is an amino acid; (X14) is an amino acid and k is between 0 and 3, preferably 0 or 1 and most preferably 0, (X15) is an amino acid with a side chain; and (X18) is present or absent and, if present, is an amino acid; and wherein the side chains of (X2), (X7) and (X15) are connected via a connecting molecule, said connecting molecule having at least three functional groups, each functional group forming a covalent bond with one of the side chains of (X2), (X7) and (X15).